Inside the GM Mindset

Welcome to the debut episode of Rosters to Rings, hosted by long-time MLB executive Thad Levine and former NBA GM Ryan McDonough. In this kickoff conversation, Thad and Ryan share their unconventional journeys to the front office and reveal the behind-the-scenes reality of running pro sports teams—what fans see and hear is just 40% of the story. Get a preview of what’s to come this season as they pull back the curtain on the strategies, decisions, and pressures that define life as a GM.

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Episode Transcript

Speaker 1 (00:05):
Welcome to the Rosters to Rings podcasts, where general managers
from all major sports, including Major League Baseball, the NBA,
and the NFL, will take you behind the curtain and
share their unfiltered experiences breaking down all of the major
sports events today and in the past. I am fad Levine.
I've spent twenty five years working in Major League Baseball

(00:26):
for the Los Angeles Dodgers, the Colorado Rockies, the Texas Rangers,
and the Minnesota Twins. In my career, I've negotiated over
a billion dollars worth of contracts. I've participated in two
three and four team trades. I worked for a team
that went bankrupt at beginning of the season, was sold
in the middle of the season, and ultimately went to

(00:46):
the World Series in that very same season. I've tasted
the euphoria, champagne celebrations, and the utter bitterness of defeat.
I've also met some exceptional people along the way and
have had some incredible experiences and on Roster Rings, I
want to share as many of those with you as
I can. Throughout my career, I had opportunities to speak
to the media to fans alike. In my opinion, general

(01:09):
managers share about forty percent of what they know with
the fans based upon competitive reasons, league rules, mandates from
ownership in just extreme discretion. Well, here at rosterst Rings,
we aspire to share about as much of the other
sixty percent as we possibly can with you, the listeners.
Is my honor to introduce Ryan McDonough, who will be

(01:29):
my co host for the inaugural season of Rosters to Rings.
Ryan spent sixteen years working in the NBA, getting his
start in the video room with the Boston Celtics. He
attributes so much of his career success to the amazing
mentorship from ownership, the front office, and coaches alike. With
the Celtics, Ryan serves as a director of scouting, the

(01:49):
director of player personnel, and ultimately the assistant general manager.
While with the Celtics, they ended up going to the
Conference Championship three times between two thousand and eight and
two twenty twelve, winning the Conference championship in two thousand
and eight and twenty ten, and ultimately the NBA Championship
in two thousand and eight. After about ten years with
the Boston Celtics, Ryan was hired by the Phoenix Suns

(02:12):
to serve as their general manager at the age of
thirty three years old. He served in that role for
five and a half seasons. Please welcome Ryan McDonough, co
host of Rosters to Rings.

Speaker 2 (02:24):
Thanks for the glowing introduction that it's great to be
on with you and I think we have some shared experiences.
You and I know that general managers are exposed to
the best athletes in the world. We're also around a
lot of characters in this industry. There's extreme pressure on
every aspect of it, from ownership to the front office, coaches,
and especially with the players. And then there's complex and

(02:45):
challenging decision making and incredible experiences that we have to
share with you our listeners. So in Roster to Rings,
we're excited that we'll not only take fans behind the
scenes for deep dives into how decisions are made, will
also explain the how and why those decisions are made,
the strategic nature of negotiations, roster construction, and the true
depth of relationships between executives, coaches, players, agents, media and fans,

(03:11):
the people behind the scenes and the characters that make
up the game, and all the other elements that make
sports so incredibly impactful in our lives. Let me give
you a little extra color on Thad. He spent the
last twenty five years working in a variety of leadership
roles for the Rockies, the Rangers, and the Twins. The
last nineteen years he was either an assistant general manager

(03:32):
or a general manager. That has been blessed, He'll tell
you he has been blessed to be surrounded by so
many exceptional mentors. And he worked with twelve people who
became general managers, ten who became major league managers, and
other countless elite leaders. So, Sad, I'm sure working with
me is not one of the career highlights for you,
but we do the show regardless, but take our listeners

(03:54):
a little bit into your past and some of the
great people you've worked with.

Speaker 1 (03:57):
Yeah, you know, I think this will be a theme
of this show, which is just gratitude. You know, Ryan
and I have been shaped to have great success in
our careers, but it has so much to do with
the people who've invested their genuine time and efforts into
shaping us and growing us and giving opportunities to develop.
And you know, I reflect on there just so many
people would love to have these jobs, and you know why,

(04:20):
did Ryan and I get these opportunities, But not only
when we did get the opportunity did we get the
opportunities to excel. And I just think I trace it
back to the people I got a chance to work with.
You know, when I started with the Colorado Rockies, you know,
kind of unbeknownst to me, the general manager at the
time was Dan Odoud and one of his hiring philosophies,
which it was passed down from John Hard, who is
a borderline Hall of Fame general manager, was always hire

(04:42):
people who are extremely intelligent and capable, and then hold
them accountable to succeed at levels they never thought they
could succeed. And so Dan, you know, I'm not sure
if this was ultimately the plan, but seven people who
work there of the fifteen were working the front office
at the time, which kind of dates us because now
these front offices are so much bigger. But seven of
us went on to be general managers of Major League

(05:03):
Baseball teams, and an eighth guy went on to be
a manager of a big League team. And so that
was my proving ground. That was where I got my start.
I was the most junior person there of that group,
and I got to learn from each and every one
of those guys and from Dan. So it was just
such a blessing to be in those environments as a
youngster in the game, to be open minded, to grow

(05:25):
and learn, and then being just taken along for the ride.
And then here we are and now, you know, I
think Ryan and I will reflect on the chances to
give back in our careers, but more than anything, that's
part of the format of this podcast is for us
to give back and to share our experiences with people
who not only do work in the game, or maybe
who do aspire to work in the game. So, you know, Ryan,

(05:46):
take us into a few of the topics that you
think we may hit on as as we reveal and
get behind this curtain and show the fans some of
those glorious experiences we've had throughout our careers.

Speaker 2 (05:57):
Yeah, I think the main thing that our listeners will
come from this with, at least I hope it is
he is the roller coaster that it is to work
for a pro team, whether it's Major League Baseball, NBA
or otherwise, And to give our listeners a feel for that,
I'll take you back to the two thousand and seven
NBA offseason. I had been in the Boston Celtics for
four years as a much younger man, and we were

(06:19):
coming off not only the longest losing streak in the
illustrious history of the Boston Celtics. We lost eighteen games
in a row, but we finished that season at twenty
four and fifty eight, which was the second worst year
in the history of the Celtics. And so after that
brutal season, Thad We're slotted second in the two thousand
and seven draft lottery, had high hopes. Keep in mind
that was to Greg godin Kevin Durant draft, but when

(06:41):
the ping pong balls were drawn, we dropped all the
way down to fifth, which was the lowest possible pick
slot we could have in that you know, I want
to tell you that, you know, eighteen years later, it
was you know, we saw this coming, or we you know,
look back in hindsight and were calm and collected. Really,
I think we're all warnering how long are we going
to be a Loyd. We're going to get fired pretty soon,

(07:02):
because you know, coming off a disaster season and then
having a disastrous lottery result, those are the tenuous moments.
I think that you and I can can share with
the listeners just how fragile it is sometimes working for
a professional team.

Speaker 1 (07:14):
Ran, do you remember, like where you were when you
saw you guys dropped from two to five and what
was that ament? So what role were you in at
that time and what was your feeling and who were
you surrounded by and what was their reaction in that moment?

Speaker 2 (07:28):
Yeah, I remember it vividly that in two thousand and
seven on lottery night, we all watched it at the
Boston Celtics practice facility in Waltham, Massachusetts. Danny Ainge was
our general manager, Doc Rivers was our head coach, and
ESPN brought in cameras to watch us and watch our
reaction and we were told that they were not going
to use the reaction shots unless we won the lottery

(07:49):
or got the second pick, which was the expectation. Well
you probably guess what happened next. The headline on Sports
Center that night is, you know, disaster and Boston Celtics
fall to five. And you know, I one of Danny
Andrew Doc Rivers, I can't remember which one took his
hat off and kind of slammed it down. The other
was running his Uh you know, his hand through his
hair saying oh man like and so so that was

(08:10):
that was tenuous. And again that was Greg Odin one,
Kevin Durant two. We were five. But but luckily that
and then this tould be a key I think for
us throughout the show thanks to some good moves. I mean,
we drew what we thought was a bad draw, a
short straw, so to speak. But thanks to some brilliant
moves by Danny aing RGM that offseason, instead of picking five,

(08:32):
which was Jeff Green, we ended up doing a deal
on Draft night with the Seattle SuperSonics. We were able
to bring in Ray Allen to Boston to play alongside
Paul Pierce. And then later that summer we were able
to hold enough assets out of that deal to then
go get Kevin Garnett from the Minnesota Timberwolves to add
to our roster. So we'd had Paul Pierce, we Hadrajian Rondo,
who was entering his second year point guard. We added

(08:53):
two other Hall of famers, and that we weren't sure
how it was going to work, to be honest with
you, you know, and we're sitting there in training camps and
I think we're going to be pretty good. Well, the
team started twenty nine and three, one of the best
starts in NBA history. We went on to win sixty
six games that year. That forty two win season to
season improvement is still the largest in NBA history by

(09:14):
a pretty significant margin. So, you know, a few months
after that we won the championship. Not only do we
win in two thousand and eight, we beat the Lakers,
you know, the story rivals of the Boston Celtics, in
a game six beat down. So that was neat. That's
what I think you and I will be able to
share with our listeners, the highs and lows. Unfortunately, you

(09:34):
and I have examples on the other end. Two when
you're in the finals, you think you're going to win
the championship, you're right there. But this job more than
anything that and being in pro sports, I think you
and I both agree. My experiences have made me realize
and be fortunate enough to never have a real job,
and that's some of what we want to take our
listeners inside too. Yet you know how you and I

(09:55):
came up. We'll have a number of guests on who
will talk about their pass and the different roles they've
had in pro sports as well. And for me, as
I look back, you know, I've been around a number
of fascinating people. I've been paid to travel all over
the country and across the world scouting players. And now
as I started in my early twenties, I'm in my
mid forties. My good fortune continuesta because instead of getting

(10:17):
a real job, I can come do this podcast with
you and you know, maybe maybe make a few bucks
on the side, but more importantly bring our listeners behind
the curtain in into a front office.

Speaker 1 (10:27):
Yeah, a wonderful breakdown, Ryan, and I got to be honest, like,
I've got like fifteen questions myself. I can only imagine
what the listeners are thinking when they hear that. I'm
going to hit you with a few and then I'm
going to save some of it for because we should
do a full episode on that whole turnaround you guys had,
that draft, you guys had. But one of the questions
that hits me in the top is that you mentioned Odin,
you mentioned Durant. As you guys are sitting there, You're

(10:49):
I'm sure contemplating, Okay, who would we select it too?
And maybe the answer is just whoever of that two fail.
To you, you're not contemplating selecting five. Ultimately, as you
and Stanny aged, we've some magic. After the ping pong
ball comes up and you guys are five, I think,
to me, that really illuminates the fact that you know,

(11:10):
in sports, you always do have a plan A, but
tomorrow's plan A is today's plan B. And I think
the people I've worked with who've had the most success,
resounding success, they always are thinking three D chess. You know,
it's always thinking about, Okay, what's Plan A, Plan B,
Plan C. Like you never can just have one plan,
and then when that plan gets foiled, you you get derailed.

(11:32):
Like those are the people who unfortunately have sustained failure
in the game, because the game doesn't allow for you
just to have one path to success. You have to
you have to be able to adjust. And as crushing
as I'm sure that moment was, where you guys probably
hadn't even contemplated who on earth would we select five,
that's not something you had to consider. You now, all

(11:53):
of a sudden, are thrust into a situation where you
know you mentioned it. The headline's written, the devastation and being,
and now all of a sudden you have to pick
up the pieces. And not only did you pick up
the pieces, but you go and acquire two guys who
are you know, top fifty players of all time, they're
Hall of famers, they're in their prime, and they take
you to a championship. Do you have a sense of

(12:15):
if you had dropped to three, if you had dropped
to four, if you had stayed a two, does Danny
make those trades or do you guys stand pat and
make the most of that draft? And have you ever
wondered what would be the trajectory of the franchise if
you had just stayed put and taken Jeff Green, or
if you'd taken whomever it was the right guy at
three or four?

Speaker 2 (12:33):
There one of the debates internally that was Greg Oden
versus Kevin Durant for sure, especially if we got the
number one pick, because if we got the number two pick,
it was more likely, I think to b Durant because
we projected that Odin was going to go number one.
And you know, one of the challenges when you're on
the team side that is, you know there are medical

(12:53):
situations that come up to that you can't go out
and say well, we have concerns about this player. Know,
you could get in a lot of trouble not only
with the player, his agent, with the league office. You
could get sued for violating hippo laws and things like that,
so you do have to be careful. But yeah, all
of that factored into the equation. And we went through
that process for the fifth pick, because that trade with

(13:17):
the Seattle SuperSonics in which we brought back Ray Allen
from Seattle to Boston was not consummated until draft, if
I remember correctly, right before the draft started. So we
went through the entire process. Yeah, we looked at just
off the top of my head, Al Horford, Corey Brewer,
Jeff Greeny, giondling On, a seven foot Chinese guy who
was extremely skilled. They used to call him Chairman Yee

(13:39):
because he worked out great against a chair But we
didn't know if he could play against any other guys.
So we went through that process and it's amazing, you know,
just how that that one off season really sad swung
the careers for so many of us, myself included. You know,
Doc Rivers is now one of the winning ast coaches
in the history of the NBA. Danny Ainge is my opinion,

(14:00):
the best executive in the NBA last couple of decades,
and then three Hall of famers Paul Pierce, Kevin Garnett,
Ray Allen Rajion Rondo may be a fourth. And then
a number of guys on those staffs went on to
get general manager jobs or head coaching jobs somewhere else,
you know. In addition myself, we had Tom Thibodeau was
our defensive coordinator who's currently leading the New York Knicks

(14:21):
in the Conference finals. Lawrence Frank wanted to be not
only the head coach of the Detroit Pistons, but is
now doing a great job running the LA Clippers as
their president of basketball Operations. So I think that's one
of the other interesting things that we'll share with our
listeners and bring them behind the curtain on, is how
many of us are connected you and Major League Baseball,
me and NBA and sometimes even across sports given our relationships.

(14:44):
But those connections, those relationships and kind of the origin stories,
you know, where we started and as you know that
for all of us, it's never a straight line, but yeah,
to take us behind, you know, kind of some of
year background we've talked a lot about the Celtics, you know,
I know, you know, Rockies, Rangers and Twins, especially with
the Rangers. You guys were close. What are some of
the things that you want to share with our listeners

(15:05):
just about you know, the times you want and the
times you were right there and it slipped away.

Speaker 1 (15:09):
You know, Ryan just talked about one of the best
turnarounds in NBA history. Chance to go from that two
thousand and seven season, which was a little bit of
a scuffle, to the heights of the two thousand and
eight winning a championship. Well, I'll give you a near
miss story, which was, you know, something that really shaped
me in You know, I think we can all attest
the fact that nothing galvanized as a fan base like
an abject failure. And you know, you hear about the

(15:31):
lovable losers with the Cubs and the Boston Red Sox
for a long time notorious, and you know, Golden State
had such a long drought before they've had this tremendous
run and a lot of the things that galvanize those
fans is all those losing seasons. Well, I'll give you
a galvanizing moment for you. So I'm dating myself back
to the twenty eleven World Series. The Texas Rangers are

(15:51):
playing the Saint Louis Cardinals. For those of you who
haven't been utterly scarred throughout your whole life by this
this series, I'll paint the picture that the Rangers were
up three to two in a best of seven. We
go to Saint Louis, Game six, We got a head
of steam behind us. The game gets rained out, despite
the fact that not a drop of rain falls from

(16:13):
the sky, which was probably the first omen that something
was about to go badly arrive for the team. But
fast forward to the eighth inning. We're going into the ninth.
We're up seven to five with three outs to get
before we give up two runs. We had a ninety
eight percent chance to win, which is one of the
more crushing advancements in analytics is that you know at

(16:35):
any point in any game exactly what your odds are
to win. Well, we had a two percent chance to lose,
and just you wait. So they ended up tying it
in the ninth in a absolutely devastating fashion, and they
ended up winning it in extra innings. So we are crushed.

(16:56):
I'm watching the game in the stands we trudge into
the club house. Things had happened so quickly that all
of the lockers were taped off. The Champagne was sitting
in the hall on Ice, the opposing team's general manager,
had come down to congratulate us. He retreated from the room.
We walk into the clubhouse and it's like a morgue.

(17:17):
They're grown, grown men crying, and we walk into the
manager's office. It's me John Daniels, the general manager at
the time, Nolan Ryan, who was the president of the team,
Ron Washington's the managers. It's silent, deathly silent. And Ron,
who is just one of the most effervescent people I've
ever met in my life, just looks at us and says,

(17:40):
can you bleep and bleep bleep bleep? What just happened
in that game? That was one of the most amazing
games I've ever seen in my life. And he was
like he was extremely energized by it, and it was like,
you know what, he was dead right. It was a
game that people will talk about forever because of the
ninety eight percent chance to win and two percent chance
to lose. In the moment, it didn't feel like the
exact right time to be expressing exuberance about how powerful

(18:04):
that game was. But that was a game that I
will never forget in my life because we came so close,
and the listener will not be surprised to hear despite
the fact that that was only game six and now
is three to three, we ended up losing Game seven
as well. We do not triumph. It takes another decade
before the Texas Rangers ultimately win the World Series for

(18:26):
the first time in franchise history. But we literally had
victory snatched from us in a very unceremonious way, and
it's something that really drove me for the next fifteen
years of my career.

Speaker 2 (18:39):
Both ad In one of the future episodes, after you
break down that twenty eleven World Series, I'll share my
experience of the twenty ten NBA Finals the year prior,
very similar experience. I was with the Boston Celtics. We
were up three games to two against the Lakers, again
the second time in three years those two teams had
met in the NBA Finals. That was under the old

(18:59):
two to three two format in terms of finals games
where the lower ceded team had three consecutive games in
the middle. Games three through five were in Boston. We
were up three to two heading to LA and then
it really went off the rails in LA. We'll get
we get into that and break that down, because you're right,
it was so fragile, and that's what a lot of
people don't realize. DNAs was great emphasizing that in Boston,

(19:21):
to try to take advantage of your window in your opportunity.
And one of the things that really stands out to
meet that is we're recording this show the NBA Conference
Finals are about to get underway, and the fragility of
it as we look at the NBA playoffs this year, well,
the Boston Celtics, the defending champions or without Jason Tatum,
not only from this year, they've been eliminated but likely
for most of all of next season as well. The

(19:43):
Golden State Warriors were as good as any team in
the NBA. They were a championship caliber club. After they
acquired Jimmy Butler from Miami, they are out as well.
They were up one to zero against Minnesota, Steph gets
injured in Game one in the first half. They going
to win the game, but then without if they lose
four games in a row, So I think those are
some of the things that we will take our listeners

(20:05):
behind the curtain, Fad, just in terms of that fragile nature.
And it's one of the things that you and I
have talked about a lot off air too, just how
much luck plays into it. As much as we don't
want to admit it, it's impacted our careers, certainly, both
positively and negatively. And I think with some of the
other guests, whether it's players, coaches, or executives, we'll talk about,

(20:27):
you know, some of the breaks they got along the
way and sometimes where it didn't go that way. And
that's one of the fascinating things to me about sports.
It's not scripted, it's not predictable. Historically, in the NBA,
you need to win sixty plus games to win a championship,
and usually if you win sixty plus games, you're at
least in the conference finals, if not the NBA Finals. FAD.
We just saw in the first two rounds of the playoffs,

(20:48):
the sixty one win Celtics are out, the sixty four
win Cavaliers, the number one seed in the Eastern Conference,
is out, and then the sixty eight win OKC thunder
who had one of the best seasons in NBA history.
We're teetering and on the ropes against the Denver team
that was depleted. So that I think that's you know,
those insights managing the emotions from a player, coach, executive standpoint,

(21:12):
I think that'll be you know, fascinating to bring our
listeners behind the scenes and maybe maybe a little bit
you know, therapy for me and you kind of going
back and forth with that. You know, we're living some
of these moments, remembering the good, and maybe we can
put to rest some of the bad that we still
linger after after all these years.

Speaker 1 (21:30):
Well, we guarantee to the listeners this won't be just
therapy sessions for me and Ryan to dump all of
our tragic stories on you. There will also be some
some stories of triumph there. But hey, listen that that's
exactly the reason we're calling it Rosters to Rings. We're
going to try to try to cover the strategy of
opening day rosters and putting those together, and then how
we every strategic step along the way to get to

(21:52):
winning a championship, bring and like everything in between. Like that,
that is our goal in bringing the listeners into those conversations,
and we're going to be able to offer the general
manager's perspective, a perspective that you know, we feel, by
and large is often muted because we have this we're
consumed with this notion of competitive advantages and not wanting
to reveal too much to the fans and to ultimately

(22:14):
to our opposition. But we're not no longer in the seats.
We get to do that. And so one of the
things we want the listeners to hold us to is
we're used to answering questions in general managers speak, where
we speak kind of in riddles. We want to speak
very transparently to you, so like, call us out when
you feel as if we're not giving those transparent, heartfelt answers.
Will be here for that. And you know, another thing

(22:36):
that I look at when I'm looking at the NBA
playoffs and something Ryan I really want to get your
perspective on in future episodes is kind of this notion
of you know, when you're building a championship team, there's
an adage that you need to have a veteran presence
on your team, Otherwise, if people haven't been there, they're
going to get overwhelmed by the moment. But yet, you know,
one side of the coin. You know, one of the

(22:56):
teams you didn't mention, but the two seed in the
Western Conference, the Houston Rockets. It was one of the
younger teams, not the youngest team in the playoffs, but
one of the younger teams, and they ended up losing
to a much more veteran team in the first round.
I yet, that same veteran team showed some injuries in
the second round and got beat by very young teams. So,
you know, sometimes we hear definitively you have to have

(23:17):
this veteran core to be able to overcome the pressures
and the trials and tribulations that the playoff process has.
In other sides of the coin, I think you see
that sometimes these youth movements really pay off because they're
probably slightly less likely to get injured. But sometimes not
knowing the pressure of the moment is powerful, you know.
And I certainly have worked with teams with rosters where

(23:39):
we got into playoff situations, and it was actually the
veterans who I think struggled in that moment because they
understood the magnitude of being in the playoffs. They were
maybe a little bit apprehensive that this was the last
time they ever were going to be able to play,
where sometimes the rookies play with their hair on fire.
They don't know better and they think, oh, I'm here
as a rookie. I guess we'll just go to the

(24:00):
payoffs every year, And of course that's not accurate, but
that's the exuberance with which they play and kind of
the reckless abandoned. So I think that kind of cuts
both ways. This NBA Playoffs has proven sometimes it pays
to have the veteran but as long as they stay healthy,
right because if those guys get hurt, sometimes it's a
little tougher to recover and then you really are diving
into your depth. But ran you know, we've talked about

(24:21):
this before, I'd love you to shed a little light
on the fact that we may be seeing some new
trends in the NBA playoffs right now. And two that
jump to mind that i'd love to get your thoughts on,
and maybe first we'll start with this one is just
it seemed to me that the NBA one of the
biggest shifts from regular season to postseason is how much
you would trim your rotation, and that typically in the
regular season you're playing ten to eleven guys, whereas in

(24:44):
the postseason you'd stick with your eight and maybe play
nobody past that eight. What are we seeing in this
playoffs that you feel is a little bit different.

Speaker 2 (24:52):
Well, even now that we're in the final fourth AD,
we do see some contrasts on the team's remaining. The
New York Knicks. Tom Thibodeau their head coach, who I
work with in Boston, he's kind of been the face
for anti load management frease. He's an old school coach.
He plays his starters in his top reserver two a
number of minutes. Really, if you look at the Knicks rotation,

(25:12):
they only play about seven guys that Mitchell Robinson comes
off the bench, as does Deuce McBride, but really that's it.
They may play other guys spot minutes here there, but
it's those seven. And it's kind of ironic. And I
wonder if it will cause teams to re visit and
reevaluate their stamps on loads management. That all these other
teams who rested guys, who limited minutes, who gave players

(25:33):
nights off and back to backs, a lot of them
have broken down that they didn't make it. That health,
as you mentioned, has been one of the key things
in the NBA playoffs in the New York Knicks, who
have the NBA's Iron Man, a guy we drafted in
Phoenix mckel bridges and others playing forty plus minutes a night.
They're thriving and they're healthy, as the Celtics and other
teams break down and fall by the wayside. And that's

(25:56):
one of the things that's so interesting in sports. We
really hope to take our listen behind the scenes on this.
That is it's copycat. It's copycat league teams copy trends
until there's something else that works or something better, and
then they shift and adapt. And so the NBA, You're
absolutely right. Forever it was the same guys seemingly in
the finals every year, Steph Curry and or Lebron James

(26:21):
and or you know the old adage, you needed guys
in their thirties to win. You needed veterans to win well.
In the final four, the best players in this year's
playoffs are all in their twenties. Tyrese Halliburton, Jalen Brunson,
Sha Gildos Alexander and then Anthony Edwards, who is currently
the same age. There's a lot of players who are
going through the draft right now. So so yeah, it

(26:41):
does shift and evolve. And one of the things that
I'm fascinated to see is if the two deepest teams remaining,
the Indiana Pacers and the OKC Thunder, advance out of
the conference finals end up playing in the NBA Finals,
will teams look at less star heavy rosters that that
was always the trends in the NBA. We need a
big three to big three. Well, frankly, the teams that

(27:02):
have big threes, looking at Philadelphia and Phoenix in particular,
haven't done very well in the hard cap era because
they don't have depth, they don't have roster balance, and
they don't have a lot of financial flexibility to make trades,
whereas the teams that have a more balanced roster and
a more balanced payroll are thriving and still playing as
we approach late May.

Speaker 1 (27:21):
And Ryan, I think you're shedding some light on the
cyclical nature of building championship rosters. You know, when your
team is less experienced, it also means they're probably less
pricey because they're less far along and they're earning cycles,
and so you know, I harken back to the twenty
ten team that went to the World Series with the

(27:42):
Texas Rangers, and we were I think like the nineteenth
or twentieth highest payroll just to retaine that same team.
Going into the next season, we jumped to the fifteenth
and then the next year we were up to the tenth.
We really hadn't fundamentally added significant talent to that team,
just the price of retaining that core. So whether you're
building that that big three where you know you're recruiting

(28:03):
those guys at free agent dollars and paying them up front,
or you're retaining them. Because I saw the comments from
Nikola Jokic where he was saying he felt that they
just didn't have the same depth that other teams had.
But that's due to run a little bit more of
the maturation of that team right where he obviously is
a superstar talent, But guys like Jamal Murray and Porter
and other guys and Gordon got paid because they matriculated

(28:26):
through the process, and to retain the talent, you had
to pay them. So it wasn't as if they recruited
him at the high price. That was just a matter
of retention. And so maybe we're looking at a team
there which is still within its window. But you know,
do you as an executive of the NBA look at
it and says, is that window starting to close? Or
they may need to change that roster because you know,
now they're on the backside of it. They've had to

(28:47):
peel off so many of those championship caliber extra pieces
that they had that put them over the top, and
now they have to singularly rely on that smaller core
group of guys. If any of those guys get injured,
they're really compromised.

Speaker 2 (29:00):
That's the cost of success, and that'll be one of
the themes on this show. When you're successful, your role
players in particular get paid someone say overpaid elsewhere based
on the performance, based on that productivity. And one of
the things is so challenging, especially if you're in a
championship window chasing the title, is trying to develop young
players at the same time, and that's almost an impossible

(29:22):
task for a head coach or a manager in the dugout,
but organizationally, that's the goal that you have guys to
replace in backfill. And you're absolutely right. The Denver Nuggets
are a real time example of that. They won the
championship in twenty twenty three, they dominated not only the
Western Conference but the Miami Heat in the finals. The
Koli Jokich was clearly the best player in the world

(29:42):
at that time. But gone from that team are their
poor role players. Contavious Caldwell Pope got a big deal
from the Orlando Magic, Jeff Green left, He's in Houston now,
Bruce Brown got a big deal from the Indiana Pacers.
So at some point in the new hardcap era, with
the second apron being so punitive in the NBA, that
you just have to let guys go and you hope

(30:04):
that you have enough young talent you're able to nail
your low cost minimum signings and fill out your roster
that way. And that's going to be a theme in
the NBA, and we'll talk a lot about that on
this show. The championship window now in the NBA is
very narrow, and I think the best real time example
that it'll be fascinating to follow over the next few
months is the Boston Celtics, last year's champion, the favorites

(30:25):
to win it again this year. We know the Knicks
played great, we know Tatum is injured, So what does
Brad Stevens and company do in Boston that And that's
one of the neat things about doing this show with
you every week is it will be able to break down,
you know, often in real time, not only reaction to
what happened, but also looking ahead to what we think
is going to happen. Because I look at the Boston
Celtics roster in payroll, I think they're going to have

(30:47):
to make some excruciating decisions. And whenever Jason Tatum comes back,
whether it's late in the year, next year, or in
the playoffs or even the season after, I think the
Celtics roster is going to look very different. And you know,
I'd love to get your take on just the disparity
in Major League Baseball. That's one of the things that
stands out for me, you know, the disparity between what
the Dodgers are doing at the high end and say

(31:08):
the Marlins at the low end, and how you operate
in each different salary range. I think that'd be fascinating,
fascinating for our listeners to hear.

Speaker 1 (31:17):
Yeah, and Ryan, you're talking about it. It's like the
cycle of winning a championship, Like we always aspire to
build something that is sustainable and you know, part of
your role as a general managers, you're constantly thinking you
have a one year, three year, and a five year
plan and they're all running kind of parallel to each other,
and you hope they all work in synchronicity with each other.
But as you just illuminated, it's incredible how quickly it derails.

(31:40):
And you think your once your windows open, that it's
wide open, and then you find out it's really one
full season. And then you know the Celtics who were
poised to strike again this year, and you know, we'll
dive There's another topic we'll dive into, is you know,
how rare is it that a team is being sold
against the backdrop of a pursuit of a second back
to back championship, Like you don't see that too often,

(32:01):
and so you know, between Ryan and my experience, like
we've been exposed to real time sales of these franchises,
but that that's pretty unique. But you know, part of
the reason that team is selling for a record is
because the expectation was that they were one of the
prohibitive favorites to not only win this year, but potentially
if everyone stayed healthy, they were going to go into
the offseason as one of the favorites. Well, you know,

(32:21):
I experienced that in baseball quite a bit. You know,
they're they're teams that you know, every year you aspire
to control what you can control. If you win your
division in baseball, you get to play home playoff games,
and that is a boon. And so then once you're
playing home playoff games, it's it's really a decided home
field advantage. And then at that point you feel like
you're you know, you take your chances, as Ryan and

(32:44):
I discussed, like based upon injuries, based upon momentum, based
upon a little bit of luck, maybe you can knock
off one of the big boys and keep rolling. But
you hope that that window is open, kind of open ended.
It's it's indefinite, and it's amazing how quickly your team
would is the young, upstar team that maybe has no expectations,
all of a sudden has a expectations heaped upon them.

(33:06):
And so to me, that was one of the biggest
distinctions between the twenty ten World Series team, the twenty
eleven World Series team, and then the twenty twelve team,
which I could argue was the best Texas Rangers roster
that we configured it lost in the first round of
the playoffs, and I think the biggest difference there was expectations.
And this will be another part of our conversation is

(33:26):
you know, keep in mind, listeners that these guys we're
talking about, these athletes are absolutely exceptional at what they do.
They are in the top one percent in the world
and what they do everything else, they are representative of
all of us. They have insecurities, they have flaws, they
have challenges at home that we all experience. They're extremely relatable.

(33:48):
Outside of the fact that they can do things above
the rim or hit balls harder than any of us
could possibly dream. The rest of it is pretty much
across section of humanity. And so twenty eleven, going into
twenty twelve, we were the prohibitive favor to get back
to the World Series and potentially win it. It was
palpable to see how the players respond to having that

(34:10):
level of expectations on them, because now, instead of just
going and playing the game, anything shy of a World
Series repeat performance would was being deemed a failure. Not
by them and not by us. That's not how we
were shaping it, but that's what the media was saying,
that's what the fans were saying, that's what the pundits
were saying, and it's hard not to listen to that.

(34:30):
And it's incredible when you see a team which was
just as talented as it was the year before, and
all that talent warranted those prognostications, but now, all of
a sudden, the mental side of the game becomes a
significant factor that plays in and I think that's part
of that winning cycle of which we speak and that's
why sometimes when you as a fan, think, wow, that

(34:50):
it felt like this team should have won for three
to five years, but they only win for one to two.
That heaping of expectations, that pressure, to me, always seemed
like a sudden when you're sprinting, you've got a parachute
behind you instead of wind at your sales. The teams
that master that and can hone that such when they
come to the ballpark every day, they not only believe
they can win, but they expect to win. I think

(35:12):
that's what propels them forward. But it takes a minute,
especially for those young teams. And I think you know,
as we talked about the merits of having veterans versus
the youth, movement. I do think that's where you know,
either the young guys have to learn that on the
fly or the veteran guys need to be able to
educate them to that, because that is a real pressure.
You know, think about what it feels like when you
walk into class and you've got a social studies test

(35:35):
that you're not prepared for, or even the one that
you are prepared for, there's a heightened anxiety. Well, imagine
playing a baseball game or a basketball game in front
of a packed house where there's pandemonium in the stands
and everyone staring at you in every movement you have,
and you're playing against the best in the world. These
guys feel pressure, they feel anxiety, they feel stressed. It

(35:55):
impacts their performance and ultimately changes sometimes the trajectory of
these championship cycles that we go through. Ran I'd like
to shift shifters. Oh, please jump in if you had
some thoughts on that.

Speaker 2 (36:07):
Now. The final thing I was going to say is
one of the things I really look forward to is
bringing on guests who can talk about how the pressure
is different with different organizations at different cycles in the
franchise of development, and with different external expectations. Whether that's ownership, pressure, payroll,
all of that. In Major League Baseball, imagine it's very

(36:28):
different being the general manager or the field manager of
the LA Dodgers and the New York Yankees than it
is trying to run the Miami Marlins or Colorado Rockies.
Those are different things. Same in the NBA. You mentioned NICOLEA. Jokic.
If you have an all time great player in its prime,
whether it's Jokic, Steph Curry, Lebron James, that year to
year pressure is real. Now it's great to have those

(36:49):
guys because they can single handily win you games, if not,
playoff series if not, sometimes carry you all the way
to a championship. But the pressure is very different than
developing a bunch of young guys. In that case. Stat
sometimes you're trying just to not let go of the
rope and keep everybody positive as the losses pile up.
So one of the neat things I think we'll do
on this show is bringing people who have done it

(37:11):
at all levels, and as you know that if you
do it long enough, usually you're at the different levels
you know you and I have been lucky to be
in the championship round. I've also been affiliated with the
worst teams in the league in Boston and Phoenix and
in the middle trying to build through the middle. It
presents its own challenges as well. So that's one of
the things I look forward to on the show, not
only you and I sharing our experiences, but bringing on

(37:32):
different guests, especially players, coaches, managers, executives, maybe even some
owners who can share with us and illuminate for our
listeners what the different challenges are in those different roles.

Speaker 1 (37:44):
Yeah, and you know baseball, as you just reference, like
it's the last major sport that doesn't have a salary cap,
and so you know, there are such different pressures in
some of those big markets. You know, it's really win
or bust in all of those, whereas I think it's
some of the smaller markets. You can define success differently.
Now you also deal with the realities. You know, I
think in baseball the last thirty years, no team that

(38:06):
didn't sit with a top fifteen Paarrol has won a
World Series, and so parody is a real concern in
that league. You know, there been fleeting successes from the
Tampa's and Milwaukee's and Minnesota's and Cleveland's of the world
but in practice that the teams that are triumphing and
winning the World Series buy and large are those those
payroll behemoths. But you know, one of the biggest distinctions

(38:26):
that Ryan and I will talk about, and we'll bring
in guys from the NFL to talk about this as well,
is the notion that in the NBA, like there probably
was a time where you could really build around one superstar,
but even the teams that Ryan referenced earlier, that those
all those teams have tremendous complimentary players on those teams
as well. Baseball you really can't do that, you know,
I think probably the pinnacle example of that, and this

(38:48):
is not to take a shot at anybody, this is
just the reality of it. Is the Anaheim Angels. You know,
for a period of time had Mike Trout and Shoe Otani,
you know, one guy who was unequivocally the best player
of his generation and coupled with a guy who's proving
to be maybe the best player now of his generation,
and not only did they not win in the playoffs,
they never actually got to the playoffs together and win together. So,

(39:10):
you know, it is really tough when you're building out
these rosters, especially in a league where there's a you know,
no salary cap and you're trying to work within payroll
parameter set up by your ownership group. The notion that
you know, it's the intoxication of pursuing that star, but
at what cost, Like what type of team can you
genuinely put around him to build what you know you

(39:32):
is required to build a championship caliber team, not just
a championship caliber corps.

Speaker 2 (39:38):
Yeah, add another interesting angle I think that you and
I can take, and we'll bring on some guests to
share their experiences as well. But if you're a commissioner
of Major League Baseball for a day, or I were
commissioner of the NBA, what changes would we make? And
I know, as you know, I look in my rolodex.
You know, Adam Silver's in it. Byron Spruell runs basketball
operations for the league, Kiki vandaway you to do the same.

(40:01):
I'd be really interested to hear from guys like that.
What changes are being discussed currently, What changes maybe have
been discussed in the past but put to bed and
then in the future. Is there anything on the horizon
the teams are looking forward to and the leagues are
looking forward to one hot button topic in the NBA
fad is expansion, with Seattle in Vegas potentially being the
two cities. So we'll have on I think a really

(40:24):
interesting cross section of guests thatad. But you know, I
threw it a couple names from league offices. I guess
I could tap into my Celtics rolodex and maybe get
on a Doc Rivers or a Danny Ainge or even
player like Rajion Rondo, James Posey. As I look at
my Phoenix Sun's time, you know, as I add up
the career in ranks for Devin Booker and mckail Bridges,
I'm not saying those guys owe me, but they're going

(40:45):
to make between a half a billion and a billion
dollars in their NBA careers. That's hopefully they get gig
us half an hour show or so on this show.
But who are some of the guys take our listeners behind.
Who are some of the guests you know you have
in mind that you would love to get on this
show at some point?

Speaker 1 (40:59):
Yeah, I got to be honest, Ryan, when you shared
with me your list of people you thought you could access,
I became a geeked out fan, I was like fired
up at the prospect, you know, just so the listeners know,
Like you know, Ryan has access to every single general
manager in the NBA. He has access to the vast
majority of the superstar players, access to owners, access to

(41:21):
every member of the media. Like, hopefully I will be
able to do the exact same thing on the baseball side,
Like if you guys want to hear from any general manager,
past or president. You know, Ryan and I are both
personal friends with theo Epstein. THEO is most likely going
to be a future Hall of Famer. He really transformed
the game meaningfully, impacting marketplaces in both Boston and Chicago.

(41:43):
Got to start over in San Diego. But he's a
personal friend to Ryan and I know, and I'm sure
he would come and share some of his wisdom with us.
Billy Bean's been one of my biggest mentors. Obviously memorialized
in the movie Moneyball, but he's been so much more
than that, And he's been the embodiment of general managers
past I think in Major League Baseball, a guy who

(42:06):
is willing to take you under his wing. Never got
a chance to work with Billy, but every year he
took an opportunity to mentor me and we had constructive
career counseling calls. Wonderful human being, exceptionally intelligent guy, dynamic
really transformed the game. I'd be fascinated to hear from him.
You know, if we had Moneyball two, which would be
the team that we would focus on, who would star

(42:26):
in it? What did he feel they got right? What
did they get wrong? And Moneyball won? And how much
did that change the trajectory of the Oakland Athletics franchise.
I look at some of the Hall of famers I've
been blessed to work with last year's Hall of Fame class,
Joe Mauer from Minnesota, Adrian Beltray from Texas, and Todd
Helton from Colorado. I was fortunate to work with every

(42:47):
single one of those guys in my stops along the
way getting one of those guys on to share their wisdom,
Paul Mollador, Greg Maddox, Jim Tomy, some other general I
mean a Hall of Famer sorry, who were gracious enough
to spend their time with me, and I've developed personal
relationships with them. If we could get those types of
guys on in addition to being some of the best

(43:08):
players of their era, their exceptional storytellers, and their preparation
for the game. Once you hear about it, you would
understand why they had the careers that they had, and
just sharing a glimpse into that would, I think would
be exceptional for the listeners. Any member of the media,
you guys want to hear from in baseball, any member
of a current front offices, past front offices, I think

(43:31):
we can access. But a lot of guys who not
only one World Series as players, but kinneley guys maybe
who fell a little bit short in their careers and
what happened along the way for them. We're going to
share each and every one of those experiences stories. One
of my best friends and mentors, Jamie Reid, always called
baseball it's a funny game with even funnier people and

(43:52):
funny stories. We want to share as many of those
funny people and funny stories with you guys along the way.
But one thing before I let you go episode run here, Ryan,
I think one of the common themes that we feel
throughout the game that we were blessed to work in
is that the tie that binds all of us together
is an exceptional passion for sports and whether that's the

(44:13):
listeners listening right now, executives who've gotten a chance to
work in it, or players. What is your origin story, Ryan,
Why did you want to pursue sports when you were
a kid? Well?

Speaker 2 (44:25):
That I was very fortunate to grow up in a
sports household with a famous father. My father, Will McDonough
is in the Sportscasters and Sports Writers Hall of Fame
in North Carolina. He wrote for the Boston Globe basically
his entire adult life for forty four years. So my
brothers and I and our sisters, we grew up in
the Boston suburbs, and our father was one of the

(44:45):
very first sports writers to cross over that from print
journalism to TV. That really didn't happen in the eighties.
Usually either an on air TV personality or a sports writer,
and you didn't do both. My dad's information was so
good that CBS initially reached out, and in nineteen eighty six
he ended up doing both. And CBS's thought was, if

(45:06):
we can get Will McDonough for one day a week,
and Boston Globe can have him the other six, but
we'll have him on Sunday breaking news. So I really
don't know if there's anybody like him in today's media.
I think maybe some combination of Adam Schefter and Adrian
Rojanowski and Jeff Passon. I mean, that's who my father was,
and I think an older generation of listeners will remember him.
And then my oldest brother, Sean. He's a long time

(45:28):
played by play broadcaster. He's done big games at just
about every level of every sport. Currently he's doing the
NHL Playoffs for ESPN and ABC. He's done the World Series,
he's done the Olympics, he's done college football semi finals,
national Championship. He's not all of that, so he is
current relevant and it would be a great guest. I

(45:49):
probably have to buy a mistake dinner to come on
and maybe bribe him with some wine, but that's that's fine.
We can work these kind of things out. And then
our middle brother, Terry Thad. He was a longtime NFL executive.
He was a member of the Baltimore Ravens front office
when they won Super Bowl five back in two thousand
and one. So, as far as we know, our family
is the only one with three brothers who have championship

(46:10):
rings from three different sports. Terry has one from the Ravens.
Sean has one from a broadcast the Red Sox in
two thousand and four, and I have one from the Celtics.
And the joke in our family was the race for two.
And now that I think about, it's been a while
for all of us, so I think we're all falling.
We're all falling well well short, but that take us
behind the scenes. Was what's your sports origin story and

(46:32):
how did you get so passionate about sports growing up?

Speaker 1 (46:35):
So I grew up in northern Virginia. My dad really
genetically passed down a love for sports to me. He
grew up in New York City. My mom grew up
in Mississippi. They ultimately decided to raise me and my
sister in Virginia. The closest team of the time was
the Baltimore Orioles, and so we'd go to about ten
games a year and we'd pile into the car, my sister,

(46:56):
my mom, my dad, and I and we would go
to a game. And I remember distinctly, I was about
five years old. I was sitting in my dad's lap.
We were sitting just to the right field side of
first base, about fifteen rows deep. An old, old memorial
stadium and a pop fly came in our area, a
foul ball. I'm sitting on my dad's lap without any
hesitation whatsoever, he voults to his feet. He drops me

(47:19):
to the ground, beer cascading down to me, hot dog
mustard face down on my chest. He ranges into the aisle,
catches the ball, and I'm just looking up at him
like incredulous. And you know, I'm thinking at the time,
I'm his favorite and only son, and he just put
me in total harm's way in the name of pursuing
this catch. He celebrates with everybody in the stands as

(47:39):
if this was unequivocally his proudest day of his life.
And keep in mind, he had been married to my mother,
he had had two children, but this was the day
that was going he was going to hang his proverbial
hat on. And I was thinking, if somebody could love
something that much that he'd forego the well being of
his only son, maybe this is something I'd want to
get involved in in my life. And so then, and

(48:01):
I'm sure we're going to hear more about stories like this.
But you know, when I graduated from college, I applied
to all thirty Major League baseball teams. I got no
response whatsoever. From twenty six I got formal rejections from
four and I was ecstatic. I was like to date
myself and Ryan and I may date ourselves a few
times in the show, so bear with us. There was
this team called the Montreal Expos. We've already referenced the

(48:25):
Seattle Superstonics, the Montreal Expos. We should have a bingo
card of all the franchises that are now defunct that
we reference. But Claude Brocho as a team president, and
he sent me a formal rejection letter, cordially inviting me
not to work for his franchise. And I was like,
I am that close. And so the passion for sports continued.
I ended up going to work for the Rebox shoe

(48:47):
company at a college, thinking that I was pretty close
to sports. Within about six months on the job, they
farmed me out to one of their subsidiaries, which was
the rock Port Shoe Company, which was a few concentric
circles away from professional athletics at that time. The demographics
of Rockport at the time was if you were a
man in a casket, you probably were wearing rock Ports.

(49:07):
That was their demo. If you were sneakers up, you
were wearing rock ports. But anyway, the journey continued from there.
The passion never subsided, and I was fortunate enough to
break in with the Colorado Rockies coming out of a
graduate school and then just never look back from there.
But we could talk more about that at some point,
but that's kind of where it all started for me.

(49:29):
And you know, another theme that you're going to just
hear from Ryan and from me and from people will
be on the show is just how incredibly blessed we
feel to have had these careers. There's so many people
who strive to work in sports. We were two of
the fortunate ones who were able to do it, and
just to work with so many wonderful people along the
way that we were allowed to sustain careers of sixteen

(49:51):
and twenty five seasons long and stay tangentially connected to
sports even after leaving the franchises that we gave our
whole careers too, so that that will be shared along
the way. But we can't wait to hear from the audience.
We want to hear what the listeners want to hear.
We're going to be back here in a week's time

(50:12):
in which we are going to dive headlong into the
conference championships and we're going to talk more about those
four rising stars that Ryan referenced and how they are
prevailing in the championship round. We're going to bring on
some people who have exceptionally keen insights into the NBA
playoff process, guests to be named later, that you will

(50:34):
hear from in the coming weeks where we break down
the NBA, and we also turn our eye to Major
League Baseball where the season is starting unfold and we're
already starting to see some surprises, you know, from the
triumphs of teams like the Detroit Tigers, the success of
teams like the Saint Louis Cardinals who kind of pin
this as a rebuilding season, as well as some of

(50:57):
the struggles at the outset of the teams that were
expected to do well, such as the Baltimore Orioles, and
then sadly that one team is on pace to break
a record in terms of run differential and total losses
within of the year, which hopefully in the next couple
of weeks we'll start writing itself. Because we don't want
to talk too much about the Colorado Rockies if we

(51:17):
can avoid it, so those will be our topics on
the horizon. We appreciate your time, we look forward to
seeing you again on Rosters to Rings with Ryan McDonough
at That Levine. Please join me host That Levine, Ryan
McDonough and other general managers every week for Roster to
Rings on Apple, Spotify, or wherever you get your podcasts.