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September 30, 2025 • 20 mins
Episode two explores the Preakness Stakes at historic Pimlico Race Course, the crucial pivot point in the Triple Crown challenge. Host Marty Sinclair reveals why this middle jewel, run just two weeks after the Kentucky Derby, serves as the great revealer of championship mettle. Listeners discover Pimlico's unique character as "Old Hilltop," its distinctive traditions including the Black-Eyed Susan blanket, and why the track's tighter turns and shorter distance create tactical challenges vastly different from the Derby. The episode examines iconic Preakness moments that derailed Triple Crown bids and validated true champions, explaining how this race separates authentic contenders from horses who simply had one lucky day in Louisville.
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Episode Transcript

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Speaker 1 (00:00):
Ladies and gentlemen, boys and girls, racing enthusiasts from coast
to coast. Marty Sinclair is back in the saddle and
ready to take you on another wild ride for the
magnificent world of Triple Crown Racing. Now, folks, as your
AI host, I've got access to every thrilling detail, every
dramatic moment, every statistical wonder, and I'm bringing it all

(00:21):
to you with the energy of a starting gate bursting open.
Welcome back to Triple Crown, and today we're diving headfirst
into the middle Jewel, the pivot point, the race that
sits right smack in the middle of racing's greatest challenge,
the Preakness Stakes. Buckle up, my friends, because we're heading
to Baltimore, Maryland, where history gets made, dreams get shattered,

(00:42):
and the road to immortality takes a dramatic turn every
single year. Now, let me tell you something about Pimlico
Race Course that'll make your heart sing with appreciation for
American sporting history. This magnificent cathedral of horse racing, located
in Baltimore, Maryland, is not just another race track. Oh No,
this is Old Hilltop, a venue so steeped in tradition

(01:03):
and character that walking through its gates feels like stepping
into a time machine that takes you back to when
racing was the sport of choice for everyone, for presidents
to every day working folks. Pinlico opened its Howood Gates
way back in eighteen seventy, making it the second oldest
racetrack in America. And let me tell you, every inch
of that place breathes history, like a living, breathing monument

(01:26):
to the sport of kings. The Preakness Stakes itself first
ran in eighteen seventy three, just three years after Pinlico opened,
and it was named after a colt called Preakness, who
won the very first dinner party states at the track.
Can you imagine that, folks, a race so important, so prestigious,
so absolutely central to the Triple Crown Challenge, named after

(01:46):
a horse that most people today have never heard of.
But that's the beautiful poetry of racing history, where the
past echoes through the present and weighs both grand and subtle,
Where every name carries a story, every tradition honors something
that came before. The character of Pimlico itself is something
that sets the Preakness apart from its Triple Crown siblings
in weighs both obvious and wonderfully nuanced. While Churchill Downs

(02:09):
gleams with its famous twin spires and Belmont Park sprawls
with its massive nane track, Pimlico presents a more intimate,
more lived in, more wonderly weathered face to the world.
It's a blue collar track in a blue collar city,
a place where the grand stands have absorbed decades of
cheers and groans, where the paint might be chipped in places,
but the soul of the joint is absolutely unbreakable. Walking

(02:31):
through Pimlico on Preakness Day feels like attending a family
reunion where everyone's invited and the party has been going
strong since eighteen seventy. Now here's where things get absolutely fascinating,
where the strategic chest match of the Triple Crown really
reveals itself in all its complex glory. The Preakness Stakes
runs at a distance of one mile in three sixteenth,

(02:52):
which is shorter than both the Derby at a mile
and a quarter and certainly shorter than the Belmont's gruelling
mile and a half. But don't let that full you
into thinking the Preakness is any easier. Oh no, no no.
This race has a character all its own, a personality
that has humbled some of the greatest horses air to
look through a bridle. The Pimlico track itself is tighter
than Churchill Downs, with turns that come up faster and

(03:14):
require a different kind of tactical awareness from both horse
and rider. Where the Derby allows for sweeping moves around
the far turn, the Preakness demands quicker decisions, sharper positioning,
more immediate responses to the flow of the race. It's
like the difference between playing chess on a full board
versus playing speed chess, where every second counts and hesitation
means defeat. The surface at Pimlico can vary widely depending

(03:38):
on weather conditions, and Baltimore in mid May can serve
up anything from brilliant sunshine to torrential rain that turns
the track into a muddy challenge that tests courage as
much as speed. But here's what makes the Preakness absolutely
critical to understanding the Triple Crown quest. What elevates it
from just another important race to the true pivot point

(03:59):
of the entire fire drama. The Preakness comes exactly two
weeks after the Kentucky Derby, right in the middle of
this compressed campaign, and it serves as the great revealer
of truth. Hold on to your hats. History is knocking.
A horse might win the Derby on sheer talent and
good fortune, might catch the racing god smiling on that
first Saturday in May. But the Preakness tells us whether

(04:21):
that Derby victory was a flash in a pan or
the real deal. It's the race that separates the authentic
championship contenders from the horses who simply had one great
day in Louisville. One New family. Think about what these
magnificent animals have endured. By the time they enter the
starting gated Pemlico. Folks, they've already run the most important
race of their lives two weeks earlier, already experienced the

(04:43):
crushing pressure of Derby Day, already had their system subjected
to the enormous physical stress that competing at racing's highest level.
Now they're being asked to do it all again before
they fully recovered, before the lactic acid has completely cleared
from their muscles, before the mental strain has had time
to Filly dissipate. It's like asking a marathon runner to
run another marathon two weeks later while carrying the weight

(05:05):
of the world's expectations on their shoulders. The traditions surrounding
the Preakness are wonderfully unique, delightfully Baltimore, and absolutely integral
to the race's identity. While the Derby has its blanket
of roses and the Belmont has its Carnation blanket, the
Preakness winner receives a blanket woven from black eyed Susans
Maryland state flower. Though here's a delicious little secret that

(05:27):
makes racing fans smile. Black eyed Susans don't actually bloom
in May, so the blanket is traditionally made with daisies
painted to look like black eyed Susans. It's the kind
of charming, practical solution that captures the no nonsense, make
it work spearing of Baltimore perfectly. The official drink of
the Preakness is the Black Eyed Susan Cocktail, a potent

(05:47):
mixture that bears absolutely no resemblance to a mint jewlip
and makes no apologies for being its own unique creation.
Deanfield at Pimlico on Preakness Day becomes one of the
wildest parties in American sports, a celebration that would make
Marty Gras look tame, where thousands of fans gather to
celebrate racing, spring and the pure joy of being alive

(06:08):
on a Saturday afternoon in Maryland. It's absolute bedlam, folks,
and I wouldn't have it any other way. The weather
gods seem to have a particular fondness for creating drama
at the Preakness, serving up conditions that range from perfect
racing weather to apocalyptic storms that turn the track into
a quadmire. Some of the most memorable Preakness races have

(06:29):
been run through sheets of rain, with horses and jockeys
covered in mud, with visibility reduced to nearly nothing, with
only courage and grick determining who crosses the finish line first.
These weather impacted races add an element of unpredictability that
makes the Preakness even more challenging, even more dramatic, even
more likely to derail a triple Crown bay before it

(06:50):
can reach the final jewel. Now, let me take you
through some of the iconic moments that have defined the
Preakness as the great pivot race of the Triple Crown,
vents that have turned what seemed like inevitable marches to
immortality into heartbreak and disappointment, or occasionally confirmed that a
horse truly belonged among the all time greats. These moments,

(07:11):
my friends, these incredible flashes of drama and destiny, are
what make the Preakness Stakes absolutely essential to understanding the
Triple Crown challenge. Cast your mind back to nineteen eighty two,
when a magnificent cult named the Looma's Ruler shocked the
racing world by winning the Preakness after finishing a distant
third in the Kentucky Derby. The Derby winner Gatto the

(07:32):
Soul finished fourth at Pimlico, and just like that, the
Triple crowd, a Triple Crown dream died before it could
fully take flight. Aloa's Ruler demonstrated exactly what the Preakness
does best. It reveals which horses can handle the quick turnaround,
which runners have the tactical speed to excel on Pimlico's
tighter oval, Which animals possessed the kind of versatility the

(07:54):
championship rusing demands. In nineteen ninety eight, Real Quiet won
both the Darby and the pre setting up a dramatic
Belmont stake showdown where he would come within a nostril
of Trickle Crown gory, losing by a nose in one
of the most heartbreaking finishes in racing history. But it
was his Preakness victory, secured despite a troubled trip in
traffic problems that would have stopped the lesser horse, that

(08:16):
proved you belonged in that Belmont starting gate with a
legitimate shot at immortality. The Preakness confirmed his class, validated
his Derby victory, and set the stage for that agonizing
near miss in New York. The two thousand and four
Preakness gave us one of the most controversial and bizarre
moments in Triple Crown history when Smarty Jones, who had
won the Derby with authority and seemed destined for greatness,

(08:38):
won the Preakness despite a false start that sent the
field off prematurely, the race was allowed to continue. Smarty
Jones won anyway, and the racing world spent days debating
what should have happened, what could have happened, what the
rules said versus what actually occurred. The controversy didn't diminish
Smarty Jones's accomplishment, but it added a layer of what

(08:59):
off speculation that still gets debated in racing circles today.
And then there's nineteen ninety three, the year of the
Great Upset that sent shockwaves through the racing world and
reminded everyone that the Preakness respects no favorites and plays
by its own rules. Prairie Bayeux, who had finished second
in the Derby behind the impressive Sea Hero, came to

(09:19):
Pimlico and dominated the Preakness field with a performance that
announced he was the horse to beat going forward. Sea Hero,
the Derby winner, never threatened, and just like that, another
triple crown dream evaporated. In the Maryland Spring air bury
By You proved that two weeks can change everything in racing,
that the horse who looked best in Louisville might not
be the best horse when the calendar turns to mid May.

(09:42):
The role of the Preakness as the pivot race becomes
even clear when we examined the horses who won the
Derby but couldn't capture the Middle Jewel, whose triple crown
aspirations died of Pimlico before they could advance to the
Belmont Test. The list reads like a who's who of
talented runners who discovered that winning one jewel doesn't care
garantee success in the next, that each race demands something different,

(10:04):
that the triple Crown challenge is precisely as difficult as
its reputation suggests. In twenty twelve, I'll have another one
both the Darby and the Preakness in thrilling fashion, displaying
the kind of grit and determination that made him a
fan favorite and had the racing world buzzing about a
potential triple Crown breakthrough. But then the day before the

(10:24):
Belmont Stakes, he was scratched due to injury, a reminder
that the physical toll of the Triple Crown campaign can
break even the toughest competitors. His Preakness victory had been
hard fought, contested every step of the way against the
formidable Bodemeister, and it showcased exactly why this middle jewel
is so crucial to the triple Crown equation. The strategic

(10:45):
importance of the Preakness cannot be overstated when analyzing successful
Triple Crown campaigns. Every horse who has completed to sweep
had to navigate the unique challenges of Pimlico had to
prove that their derby victory wasn't a fluke, had to
demonstrate the versatility and resilience necessary to win under different
conditions at a different distance on a different track. The

(11:06):
Preakness serves as both validator and eliminator, confirming which derby
winners are legitimate Triple Crown threats and exposing which one
simply caught lightning in a bottle on the first Saturday
in May. Secretariot's nineteen seventy three Preakness run remains one
of the most controversial and spectacular performances in the race's history.
Big Red won the race convincingly, but the official time

(11:29):
was initially posted as one minute fifty five seconds flat,
which would have been fast but not extraordinary. However, two
different clockers caught him in one minute fifty three and
two fifth seconds, which would have shattered the track record
and stood as one of the greatest performances in Preaknous history.
The Daily Racing Form conducted an investigation and concluded that

(11:50):
Secretariat had indeed run the faster time, though Pimico never
officially changed the record. Regardless of the exact time, Secretariot's
Preakness victory confirmed what the Derby had suggested. This was
a horse for the ages, an animal capable of achieving
the triple Crown that had eluded racing for twenty five years.
The intimate nature of Pimlico adds to the pressure and

(12:13):
drama of Preakness Day in ways that are hard to
fully convey, but absolutely essential to understanding the race's character.
While Churchill Downs holds over one hundred fifty thousand fans
on Derby Day and Belmont Park can accommodate similar massive crowds,
Pimlico's capacity is smaller, creating an atmosphere that feels more intense,

(12:34):
more focused, more immediately present. The fans are closer to
the action, the noise bounces around the facility with deafening force,
and the horses feel every outs of that concentrated energy
as they parade to the post. The tracks, quirks, and
characteristics have influenced countless Preakness results over the decades. The
turns at Pimlico come up quickly, requiring jockeys to position

(12:57):
their mounts earlier than they might at larger tracks. The
stretch run, while adequate, doesn't offer the same opportunities for
sweeping late rallies that Churchill downs provides. Courses with tactical speed,
the ability to stay close to the pace and accelerate
when it matters tend to fare better at Pimlico than
pure closers who need lots of ground to make up
in the stretch. Understanding these nuances separates the trainers who

(13:21):
can navigate the Triple Crown successfully from those who stumble
when confronted with Pimlico's unique demands. California Chrome's twenty fourteen
Preakness victory perfectly illustrated how a horse with the right
combination of speed, stamina, and tactical awareness can thride at Pimlico.
After winning the Derby with a decisive performance, California Chrome

(13:42):
came to Baltimore and won the Preakness with authority, displaying
the kind of versatility that marked him as a serious
Triple Crown threat. His ability to rate behind the pace
when necessary, then accelerate with devastating effect when asked suited
Pimlico's characteristics perfectly and set up his attempt at emial
metality in the Belmont Stakes. The Preakness has also served

(14:03):
as redemption for horses who stumbled in the Derby but
found their best form in Baltimore. Many talented runners who
encountered trouble or simply didn't fire their best race in
Louisville have come to Pimlico and proven their class with
impressive Preakness victories. These races remind us that the Triple
Crown isn't always a linear progression. That horses can improve

(14:24):
dramatically from one race to the next. At the two
weeks between Derby and Preakness can see significant changes in form, fitness,
and fortune. The tactical nature of the Preakness rewards trainers
and jockeys who can adapt their strategy to sue Pimlico's
demands while keeping an eye on the bigger picture of
the Triple Crown campaign. Winning the Preakness often requires a

(14:45):
more aggressive approach than the Derby, with riders needing to
secure a good position early and stay out of trouble
rather than relying on late runs that might not materialize
on Pimlico's tighter oval. But trainers must also balance the
desire to win the Preakness with them. I acknowledge that
the Belmont Stakes looms three weeks later, requiring them to
manage their horses energy and enthusiasm carefully. The history of

(15:07):
close finishes and dramatic stretch duels that the Preakness adds
another layer of excitement to the race's legend. The shorter
stretch at Pimlico means that races are often decided in
the final furlong, with multiple horses bearing down on the
wire and a desperate scramble for victory. These photo finishes
create heart stopping moments that racing fans remember for decades,

(15:28):
races where inches separate glory from disappointment, where horses heart
and determination matter as much as pure speed. American Pharaoh's
twenty fifteen Preakness victory came after a troubled start where
he was bumped at the break, forcing Jocky Victor Espinoza
to drop back and circle the field to secure a
clear running lane. The fact that American Pharaoh overcame that

(15:49):
difficult beginning and still one with authority demonstrated the kind
of class and versatility that championship horses possess. His Preakness
triumph confirmed that his Derby victory was no fluke and
set up his historic run to end the Triple Crown
drought that had lasted thirty seven years. The economic and
cultural impact of the Preakness on Baltimore and Maryland racing

(16:11):
cannot be overstated. This race serves as the state's signature
sporting event, bringing national attention to Maryland's rich racing heritage
and generating enormous economic activity for the region. The week
leading up to the Preakness transforms Baltimore into racing central,
with parties, events and celebrations taking over the city. Local
pride in the Preakness runs deep, with generations of Maryland

(16:34):
families making the annual pilgrimage to Pimlico, a cherished tradition
passed down through the years. The media coverage of the
Preakness has evolved dramatically over the decades, from brief newspaper
reports to comprehensive television coverage that brings every moment of
the race into homes around the Guru beadvent of instant replay,
multiple camera angles, and sophisticated analysis has transformed how fans

(16:57):
experienced the Preakness, but the fundamental drum of the race
remains unchanged. Whether you're watching on a massive high definition
screen for listening on the radio or reading about it
in the next day's paper. The Preakness delivers heart pounding
excitement that transcends medium and era. The betting patterns surrounding
the Preakness often differ significantly from burbie wagering, with handicappers

(17:18):
having to factor in recent form, recovery from the Derby
effort an ability to handle Pimilko's unique characteristics. Horses who
raced well in the Derby but finished behind the winner
often attract significant support of pin Milko as better speculate
that two weeks of recovery might flip the script. Meanwhile,
Derby winners who looked vulnerable or faced easier competition in
Louisllville often see their odds shortened dramatically as betters anticipate

(17:42):
improvement with experience and maturity. Justify's twenty eighteen Preakness victory
came in absolutely miserable conditions, with rain creating a sloppy
track that tested both courage and ability. The Big cult
handled the slop brilliantly, powering through the mud to wind,
going away, and proving he could handle any conditions thrown
at him. His Preakness triumph in the muck demonstrated the

(18:04):
kind of versatility that separates Triple Crown winners from horses
who simply have won great waste, confirming that this powerhouse
could handle the compressed schedule and varying circumstances that define
the Triple Crown challenge. The role of the Preakness in
shaping racing history extends beyond just Triple Crown narratives. Countless
horses who never competed in all three races have found

(18:25):
gory at Preakness, with Preaknous victories launching successful stud careers
and cementing legacies. The race serves as a crucial proving
ground for three year olds, regardless of their Triple Crown aspirations,
a test that reveals which horses have genuine championship credentials
and which ones need more time to develop or simply
lack the necessary class to compete at racing's highest level.

(18:47):
The maintenance and future of Pimlico itself has become a
topic of significant discussion in recent years, with debates about renovations, relocation,
and preservation of this historic venue stirring passionate reactions from
racing fans and mayorae in residence. The idea of the
Preakness being run anywhere other than Old Hilltop strikes many
as unthinkable, akin to moving the Kentucky Derby from Churchill

(19:08):
Bounds or the Rose Bowl from Pasadena. The tracks, whether
charm and historical significance, are inseparable from the Preakness Stakes itself,
making the venue's preservation a matter of cultural importance beyond
just practical racing considerations. As we close out this journey
through the middle jewel of the Triple Crown, I want
you to appreciate the Preakness Stakes for what it truly

(19:28):
represents in the grand drama of racing's ultimate challenge. This
isn't just another race between the Derby and the Belmont.
This is the crucial test that separates pretenders from contenders,
the pivot point where Triple Crown dreams either gather momentum
or come crashing down, The race that proves whether a
Derby winner has what it takes to achieve immortality or

(19:49):
with simply a talented horse who had one spectacular day.
The Preakness Stakes, run at historic Pimlico Racecourse in Baltimore, Maryland,
stands as a unique and irreplaceable jewel in Racing's crown,
a race with its own character, its own traditions, and
its own absolutely critical role in determining which horses will
get their shot at triple Crown glory. Well, folks, that's

(20:11):
all the time we have for today's thrilling exploration of
the Preakness Stakes. Thanks for listening. For more content like this,
please go to quiet please dot ai. Until next time,
This is Marty Sinplair reminding you that in Baltimore, every
third Saturday in May, the middle Jewel shines bright and
the road to immortality takes a dramatic turn. Quiet, please

(20:33):
dot ai hear what matters.
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