September 16, 2025 • 11 mins
The newest installment of ESPN’s acclaimed 30 for 30 series is the three-part documentary Berlusconi: Condemned to Win, which tells the story of Silvio Berlusconi, one of the most significant and controversial figures in Italian history over the last three decades.Serving as Italy’s prime minister over three different stints, Berlusconi first rose to prominence as a business and media tycoon who owned one of the country’s most storied football clubs, A.C. Milan. As he turned the team into arguably the world’s most successful club, he used its victories to fuel his own popularity — ultimately propelling him to the highest political office in the land. Yet as the film reveals, Berlusconi’s ascent raised troubling questions about how sport can mask corruption and provide a pathway to power with consequences far beyond the game.Berlusconi: Condemned to Win was directed by documentary filmmaker Sam Blair (Maradona ‘86, Make Us Dream, Ronnie O’Sullivan: The Edge of Everything). A graduate of the UK’s National Film and Television School, Blair made his debut with the feature, Personal Best, and later directed Maradona ’86, an ESPN 30 for 30, about Diego Maradona’s legendary performance at the 1986 World Cup. Sam also directed the feature documentary Keep Quiet which premiered in the International Competition at the Tribeca Film Festival as well as the first episode of Captive, a Netflix original documentary series, executive produced by Simon Chinn and Doug Liman.
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Good morning, Sam. How are you doing today?
Speaker 2 (00:03):
Good morning, I'm great. Thanks, how are you? Dude?
Speaker 1 (00:05):
I'm very proud of you for doing this, And maybe
it's my addiction to we didn't get here by ourselves.
It took a story to get to this moment, and
you are proving here with Bruce Askani that it's just
one of those things where there's something that happened before
we got into these glory moments of sports, where the
figures have gone on to greater things, and this really
(00:27):
really has opened up my eyes.
Speaker 2 (00:30):
Wow, that's great to hear. Yeah, I mean it's part
of the power of this story is where it takes
you somewhere you're really not expecting, the twists and turns
the layers to the story, the way it connects with politics, power, culture,
and yeah, the relationship between sport and the I guess
(00:53):
the biggest stories that we see around us. Yeah, it's
something that is important to the stands.
Speaker 1 (01:00):
It also showcases something for we Americans who you know,
take soccer or football as the rest of the world
calls it, and that it shows how powerful it is
and how magnetic it is to those that participate with
keeping these teams together. It is not just something that happens.
They need leadership and they need charisma, and this guy
has it.
Speaker 2 (01:22):
Absolutely. I mean, he was really the first modern owner,
I would say he part of what he did was
transform the sport. Soccer was really way behind the US
in terms of its understanding of marketing and how to
broadcast the game. Burnsk only understood that, so he was
(01:43):
really working on a number of levels. He remarketed soccer
he but also revolutionized the way it was played with
his choice of coaches for Milan, his understanding the sport
needed to be entertainment and needed to be a track,
and his ambition. He wanted this kind of dream combination
(02:05):
of of something that was wonderful to watch but also
one and because winning was so important to him, hence
the title Condemned to Win.
Speaker 1 (02:14):
But you know what's really interesting about him, Sam is
the fact that never once in my studies and in
watching this it I feel like that he was really
pressing the flesh flesh when it comes to this is
a business, This business needs to survive. It just felt
like that he was always about the people, the fans.
Let me give you something to talk about so that
you can have a great day today.
Speaker 2 (02:36):
Right, I mean, yeah, that's I think that's very true. Yeah,
he was very concerned with the spectacle. It's something that
and I think that's why we watched Why do we
watch sport, it's the kind of it's entertainment, it's a
kind of it's a unique space in our lives for emotion,
and I think he was really concerned with emotion and feeling,
(02:57):
you know, and that ran from when he was the
owner of TV stations through to sports and then into politics.
Speaker 1 (03:05):
Wow. Just the evolution of that, because it's one of
those situations, Sam, where you sit there and you go,
I knew you when because we know him as the coach,
and then all of a sudden we start going through
the politics and you look at the rest of the
world and you're going, oh, these politicians did what before
they got here? Well, of course they did, because you know,
Berlusconi got it right. He opened up the door for
(03:27):
the everyday average, not only person but business owner to
make a voice for themselves in the political world.
Speaker 2 (03:37):
Yeah, that's true. He really turned politics upside down in
Italy at the time. This has never happened before for
someone outside of politics to step in. I mean that's true,
but I think there was also what emerged was a
lot of problems and questions that people had about politics
being self serving. That was often one of the things
that was thrown at him was that he was using
(04:00):
politics to improve his own position and security. And so,
I mean, I think the main thing is to let
the storytell itself, but there's lots of questions to be asked.
I think about this.
Speaker 1 (04:13):
I giggled Sam because because in America that I thought
that's what politics were. I'm going to make my life
better and the rest of you will take care of
you as well as I make my life better. I
thought that was regular politics.
Speaker 2 (04:26):
Well in Europe, certainly back then, it was not the case.
And maybe, you know, he was maybe ahead of the curve.
I think he saw something that people hadn't seen before,
didn't even think was an option, and that's why he's
seen as being so influential. And we can look at
(04:48):
the trajectory of his life and his career and think
about it. You know, where did this lead Italy? Where
did it Where did his promises end up? Was it successful?
Was it not? What the problem? You know? I think
that's why it's an important story to look at.
Speaker 1 (05:03):
Please do not move. There's more with Sam Blair coming
up next ESPN's thirty for thirty. We are back with
Sam Blair. Were there other nations that were jealous? I mean,
because I know how Brazil loves their game of soccer.
I know how that you know everybody around the world,
and all of a sudden you've got this leader that's
gaining national attention and global attention because he's he becomes
(05:25):
a politician. I say, what did did did the other nations?
Were they jealous at all with that power?
Speaker 2 (05:32):
I don't know about jealous, but I mean certainly in
the football on the football stage, the soccer stage, in
this or late eighties nineties, Italy became the pre eminent
league in the world. It was where everyone looked for
the best players, the best product, as he would say,
and that a huge part of that was down to him.
(05:53):
I think the power side of it, to be honest,
I think it brought him a lot of problems. A
lot of people feel that it was he would have
been better off to stay in business in sports because
his life became one long battle really to retain his position.
It made his life incredibly complicated and in a way,
(06:15):
the sport remained simpler thing for him that he could control,
because the controlling of a soccer team compared to the
controlling of a country are miles apart. And part of
the sort of illusion that kind of fell apart was
that you could apply sporting success to a nation. You know,
I got.
Speaker 1 (06:33):
I got in kind of a sports argument because that's
what we do in sports with a good friend from
the UK, and he goes, oh, oh, oh, I know
who you're talking about. This guy thought himself as being Jesus,
And I'm going I don't even bring that up because
until I talked to Sam, I'm not ever going to
even say that. Did he really think of himself as
that powerful?
Speaker 2 (06:52):
Well, he said some he was. He would say some
outrageous things, So he wasn't shy of saying things that
were hugely controversial. But he would say one thing one
day and then the opposite the next. He he didn't,
He didn't. I don't think he seriously thought of himself
that way. But in an argument or in a heated situation,
(07:15):
he would. He would fight his corner and the sort
it became hugely polarizing. That's that's the problem. He was
not moderate at all. He was you know, in terms
of the way he expressed himself. He wasn't kind of
an ideologically driven politician. He was much more kind of
concerned with his own occult, of his own personality.
Speaker 1 (07:35):
I would say, I guess I'm just used to it
here in the States. I mean, I mean you look
at all the different owners and all the different you know,
managers and stuff like that who were all about endorsements
and making it about them. I just I kind of
invest in that. It's like, Okay, well, if they think
they're great, I'm going to I'm going to buy that.
Speaker 2 (07:50):
Yeah. I mean, it's the part. It's incredibly powerful thing
and soccer, certainly in Europe and the UK where I
am has gone down that route. It's it's huge kind
of multinational business now and their power is incredibly seductive
to see with. You know that some of the biggest
institutions in our countries, and they and they take up
(08:12):
a lot of our thought, our emotion, our focus. We
put a lot of emphasis on them, and this I
have to say, making this series really made me think
about that. But why that is and what what does
it mean? What does it say about our cultures, the
importance that these sports teams and franchises have.
Speaker 1 (08:33):
What you guys do at ESPN thirty for thirty always
blows me away. There's not a documentary that I have
missed yet because I know that you guys are going
to dig in and I do not know how you
get the B role for your storylines, but my god,
and then you add the narrator to the storyline, all
of a sudden, you've got a piece of genius going on.
What is your secret solution?
Speaker 2 (08:53):
Oh wow? I mean each film is different, each series
is different. But you know, one thing with this, like
you said, the B role such extraordinary archive material. You know,
you get to kind of time travel back through into
the eighties and nineties and see this transformation is revolution
take place, and it obviously, you know, it happened in
real time, it happened in the news on television, and
(09:15):
so we put a lot of work to kind of
excavate this material which brings that time back to life.
And then it's about exploring that with character, with people
who witnessed it, people are involved in it through interview.
You know, one of the interesting things with this is
the feelings are often just still so present in people
and the conflicts they had. Life isn't simple. People aren't simple.
(09:39):
Berlusconi was a complex, contradictory person, and so that makes
it fascinating to explore. You know, we want to be
in the middle of this story, wondering what's going to
happen next, but also wondering why, examining our own response
to it.
Speaker 1 (09:53):
I think, don't you think his superpower was that smile?
Oh my god, when that man smiled for summary, then
I felt it, and like this is old film, and
I still felt it even today.
Speaker 2 (10:06):
Yeah, he was very and everyone agrees he was incredibly charismatic.
He brought a kind of a lightness, particularly to politics.
You know, there was the politics was incredibly dour in
Italy when he emerged, so of course he was this
completely new kind of image and image was something he
was incredibly aware of, and he was really at ease
(10:28):
in front of the camera. So you know, these are
all incredibly powerful things. So yeah, he's no questioning he
was magnetic and charismatic.
Speaker 1 (10:37):
I can't thank you enough for something like this because
what it's done is it's led me into doing my
own research about other owners and other coaches and things,
especially when it comes to soccer, because it's getting to
be so big here and if I am not caught
up with my soccer history, then I don't look like that.
I'm a fan.
Speaker 2 (10:54):
Absolutely well yeah, I mean again, if you look at how,
like I said, in the UK, soccer went from being
being something that was owned by a small local businessman
soccer teams now they're owned by nation states, some of
the most powerful people in the world. So that that's
within my lifetime we've seen such a huge change and
(11:14):
you really wonder where it's heading, where's it going to
go next? And yeah, what what does for what does
soccer mean in that context?
Speaker 1 (11:22):
You got to come back to this show anytime in
the future. Sam. The door is always going to be open,
and this story is not done yet.
Speaker 2 (11:30):
Thank you so much. Being the real pleasure of talking
to you.
Speaker 1 (11:32):
You'd be brilliant today. Okay,
Good morning, Sam. How are you doing today?
Speaker 2 (00:03):
Good morning, I'm great. Thanks, how are you? Dude?
Speaker 1 (00:05):
I'm very proud of you for doing this, And maybe
it's my addiction to we didn't get here by ourselves.
It took a story to get to this moment, and
you are proving here with Bruce Askani that it's just
one of those things where there's something that happened before
we got into these glory moments of sports, where the
figures have gone on to greater things, and this really
(00:27):
really has opened up my eyes.
Speaker 2 (00:30):
Wow, that's great to hear. Yeah, I mean it's part
of the power of this story is where it takes
you somewhere you're really not expecting, the twists and turns
the layers to the story, the way it connects with politics, power, culture,
and yeah, the relationship between sport and the I guess
(00:53):
the biggest stories that we see around us. Yeah, it's
something that is important to the stands.
Speaker 1 (01:00):
It also showcases something for we Americans who you know,
take soccer or football as the rest of the world
calls it, and that it shows how powerful it is
and how magnetic it is to those that participate with
keeping these teams together. It is not just something that happens.
They need leadership and they need charisma, and this guy
has it.
Speaker 2 (01:22):
Absolutely. I mean, he was really the first modern owner,
I would say he part of what he did was
transform the sport. Soccer was really way behind the US
in terms of its understanding of marketing and how to
broadcast the game. Burnsk only understood that, so he was
(01:43):
really working on a number of levels. He remarketed soccer
he but also revolutionized the way it was played with
his choice of coaches for Milan, his understanding the sport
needed to be entertainment and needed to be a track,
and his ambition. He wanted this kind of dream combination
(02:05):
of of something that was wonderful to watch but also
one and because winning was so important to him, hence
the title Condemned to Win.
Speaker 1 (02:14):
But you know what's really interesting about him, Sam is
the fact that never once in my studies and in
watching this it I feel like that he was really
pressing the flesh flesh when it comes to this is
a business, This business needs to survive. It just felt
like that he was always about the people, the fans.
Let me give you something to talk about so that
you can have a great day today.
Speaker 2 (02:36):
Right, I mean, yeah, that's I think that's very true. Yeah,
he was very concerned with the spectacle. It's something that
and I think that's why we watched Why do we
watch sport, it's the kind of it's entertainment, it's a
kind of it's a unique space in our lives for emotion,
and I think he was really concerned with emotion and feeling,
(02:57):
you know, and that ran from when he was the
owner of TV stations through to sports and then into politics.
Speaker 1 (03:05):
Wow. Just the evolution of that, because it's one of
those situations, Sam, where you sit there and you go,
I knew you when because we know him as the coach,
and then all of a sudden we start going through
the politics and you look at the rest of the
world and you're going, oh, these politicians did what before
they got here? Well, of course they did, because you know,
Berlusconi got it right. He opened up the door for
(03:27):
the everyday average, not only person but business owner to
make a voice for themselves in the political world.
Speaker 2 (03:37):
Yeah, that's true. He really turned politics upside down in
Italy at the time. This has never happened before for
someone outside of politics to step in. I mean that's true,
but I think there was also what emerged was a
lot of problems and questions that people had about politics
being self serving. That was often one of the things
that was thrown at him was that he was using
(04:00):
politics to improve his own position and security. And so,
I mean, I think the main thing is to let
the storytell itself, but there's lots of questions to be asked.
I think about this.
Speaker 1 (04:13):
I giggled Sam because because in America that I thought
that's what politics were. I'm going to make my life
better and the rest of you will take care of
you as well as I make my life better. I
thought that was regular politics.
Speaker 2 (04:26):
Well in Europe, certainly back then, it was not the case.
And maybe, you know, he was maybe ahead of the curve.
I think he saw something that people hadn't seen before,
didn't even think was an option, and that's why he's
seen as being so influential. And we can look at
(04:48):
the trajectory of his life and his career and think
about it. You know, where did this lead Italy? Where
did it Where did his promises end up? Was it successful?
Was it not? What the problem? You know? I think
that's why it's an important story to look at.
Speaker 1 (05:03):
Please do not move. There's more with Sam Blair coming
up next ESPN's thirty for thirty. We are back with
Sam Blair. Were there other nations that were jealous? I mean,
because I know how Brazil loves their game of soccer.
I know how that you know everybody around the world,
and all of a sudden you've got this leader that's
gaining national attention and global attention because he's he becomes
(05:25):
a politician. I say, what did did did the other nations?
Were they jealous at all with that power?
Speaker 2 (05:32):
I don't know about jealous, but I mean certainly in
the football on the football stage, the soccer stage, in
this or late eighties nineties, Italy became the pre eminent
league in the world. It was where everyone looked for
the best players, the best product, as he would say,
and that a huge part of that was down to him.
(05:53):
I think the power side of it, to be honest,
I think it brought him a lot of problems. A
lot of people feel that it was he would have
been better off to stay in business in sports because
his life became one long battle really to retain his position.
It made his life incredibly complicated and in a way,
(06:15):
the sport remained simpler thing for him that he could control,
because the controlling of a soccer team compared to the
controlling of a country are miles apart. And part of
the sort of illusion that kind of fell apart was
that you could apply sporting success to a nation. You know,
I got.
Speaker 1 (06:33):
I got in kind of a sports argument because that's
what we do in sports with a good friend from
the UK, and he goes, oh, oh, oh, I know
who you're talking about. This guy thought himself as being Jesus,
And I'm going I don't even bring that up because
until I talked to Sam, I'm not ever going to
even say that. Did he really think of himself as
that powerful?
Speaker 2 (06:52):
Well, he said some he was. He would say some
outrageous things, So he wasn't shy of saying things that
were hugely controversial. But he would say one thing one
day and then the opposite the next. He he didn't,
He didn't. I don't think he seriously thought of himself
that way. But in an argument or in a heated situation,
(07:15):
he would. He would fight his corner and the sort
it became hugely polarizing. That's that's the problem. He was
not moderate at all. He was you know, in terms
of the way he expressed himself. He wasn't kind of
an ideologically driven politician. He was much more kind of
concerned with his own occult, of his own personality.
Speaker 1 (07:35):
I would say, I guess I'm just used to it
here in the States. I mean, I mean you look
at all the different owners and all the different you know,
managers and stuff like that who were all about endorsements
and making it about them. I just I kind of
invest in that. It's like, Okay, well, if they think
they're great, I'm going to I'm going to buy that.
Speaker 2 (07:50):
Yeah. I mean, it's the part. It's incredibly powerful thing
and soccer, certainly in Europe and the UK where I
am has gone down that route. It's it's huge kind
of multinational business now and their power is incredibly seductive
to see with. You know that some of the biggest
institutions in our countries, and they and they take up
(08:12):
a lot of our thought, our emotion, our focus. We
put a lot of emphasis on them, and this I
have to say, making this series really made me think
about that. But why that is and what what does
it mean? What does it say about our cultures, the
importance that these sports teams and franchises have.
Speaker 1 (08:33):
What you guys do at ESPN thirty for thirty always
blows me away. There's not a documentary that I have
missed yet because I know that you guys are going
to dig in and I do not know how you
get the B role for your storylines, but my god,
and then you add the narrator to the storyline, all
of a sudden, you've got a piece of genius going on.
What is your secret solution?
Speaker 2 (08:53):
Oh wow? I mean each film is different, each series
is different. But you know, one thing with this, like
you said, the B role such extraordinary archive material. You know,
you get to kind of time travel back through into
the eighties and nineties and see this transformation is revolution
take place, and it obviously, you know, it happened in
real time, it happened in the news on television, and
(09:15):
so we put a lot of work to kind of
excavate this material which brings that time back to life.
And then it's about exploring that with character, with people
who witnessed it, people are involved in it through interview.
You know, one of the interesting things with this is
the feelings are often just still so present in people
and the conflicts they had. Life isn't simple. People aren't simple.
(09:39):
Berlusconi was a complex, contradictory person, and so that makes
it fascinating to explore. You know, we want to be
in the middle of this story, wondering what's going to
happen next, but also wondering why, examining our own response
to it.
Speaker 1 (09:53):
I think, don't you think his superpower was that smile?
Oh my god, when that man smiled for summary, then
I felt it, and like this is old film, and
I still felt it even today.
Speaker 2 (10:06):
Yeah, he was very and everyone agrees he was incredibly charismatic.
He brought a kind of a lightness, particularly to politics.
You know, there was the politics was incredibly dour in
Italy when he emerged, so of course he was this
completely new kind of image and image was something he
was incredibly aware of, and he was really at ease
(10:28):
in front of the camera. So you know, these are
all incredibly powerful things. So yeah, he's no questioning he
was magnetic and charismatic.
Speaker 1 (10:37):
I can't thank you enough for something like this because
what it's done is it's led me into doing my
own research about other owners and other coaches and things,
especially when it comes to soccer, because it's getting to
be so big here and if I am not caught
up with my soccer history, then I don't look like that.
I'm a fan.
Speaker 2 (10:54):
Absolutely well yeah, I mean again, if you look at how,
like I said, in the UK, soccer went from being
being something that was owned by a small local businessman
soccer teams now they're owned by nation states, some of
the most powerful people in the world. So that that's
within my lifetime we've seen such a huge change and
(11:14):
you really wonder where it's heading, where's it going to
go next? And yeah, what what does for what does
soccer mean in that context?
Speaker 1 (11:22):
You got to come back to this show anytime in
the future. Sam. The door is always going to be open,
and this story is not done yet.
Speaker 2 (11:30):
Thank you so much. Being the real pleasure of talking
to you.
Speaker 1 (11:32):
You'd be brilliant today. Okay,
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