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Maldini’s Milan

Maldini’s Milan


Paolo Maldini helped AC Milan win the Champions League five out of the seven times they’ve won it. But the last time they won was 2007. So why are the team now a shadow of their former selves?


Hi, I’m Chloe and this is the Playmaker.

One story every day to make sense of the world of football. 

Today… AC Milan have moved on. Is it time we shifted our opinions of them too?


When someone mentions the name Paolo Maldini… what do you think of?

Style? Elegance? Defensive prowess? Longevity? A serial winner…? 

He’s one of those players that has almost universal appeal. 

“Few players can boast of a career spanning three decades at the very highest level. Fewer still are loyal to just one club.”

“His association with the club is a fairytale, really.”

“One of the finest defenders football has ever produced, this true legend of the game has become the very embodiment of this truly legendary club.” 

Sky Sports

The red and black half of Milan has won the Champions League an astonishing seven times. And Maldini was on the pitch for five of those triumphs. 

Paolo Maldini made football fans realise the importance of positioning when it comes to defending…when he famously said… “if I have to make a tackle, I have already made a mistake.”

The last time Milan won the Champions League? 2007. 

“A miracle in Istanbul. But no miracle in Athens tonight for Liverpool. AC Milan are European Champions.”

“Another winner’s medal for the Captain Paolo Maldini.”


So when Milan played Liverpool in the Champions League last week, fans were ready for another epic battle at the famous San Siro stadium.

And if so, they were to be disappointed, for it became clear very soon that this was not the Milan of old. 

“AC Milan are out of Europe, Atletico Madrid have gone through with Liverpool. It’s finished AC Milan one, Liverpool two. 

BT Sport

The gulf between these two sides was much wider than the scoreline suggested: Liverpool had put out a mostly reserve side. 

Milan exited the Champions League, having ended up bottom of their group.

Maldini – now in charge of transfers at Milan – was keen to emphasise Liverpool’s quality after the match. 

Which begs the question: why are AC Milan, for so long a giant of the game, a shadow of their former selves?

The unravelling of AC Milan started not long after that famous win over Liverpool in 2007. That incredible team…Maldini, Gattuso, Pirlo, Nesta etc… were getting old. 

The club owner, the former Prime Minister of Italy, Silvio Berlusconi, knew he had a huge task on his hands to replace them.  His attempts to do so failed. 

And he decided to sell the club to a Chinese investor – Yonghong Li – in 2016.

But the Chinese government decided to restrict spending on foreign football teams. Li couldn’t get his money out of China. 

And so he borrowed money from an American hedge fund… Elliott Management. And they had a ruthless reputation. The Financial Times describes them as a “Vulture Fund.” 

The repayment schedule was tough to fulfil. And Li defaulted. 

Elliott seized control of the club.

They appointed Ivan Gazidis as CEO.  He is the former chief executive at Arsenal. 

Maldini returned to take charge of the transfers. 

He brought his former team-mate Zlatan Ibrahimovic back to the club. He’s scored seven goals in seven starts for Milan this season… at the age of 40.

And of course, Zlatan brings a winning mentality to a squad that still has plenty to learn. That leadership has clearly helped the Coach, Stefano Pioli. Milan currently sit second in the league.

Maldini has also captured 23-year-old Englishman Fikayo Tomori from Chelsea. And when he earned a call to the England team in October, Tomori told the press about what it’s like to work under Maldini.

“When he was speaking to me I was kinda like whoa… it’s Paolo Maldini so you know there is that kind of pressure knowing that he’s watching every game, he’s there at the training ground every day so… me being a defender you’re kinda like yeah I wanna impress him.” 

“He’s really um… really engaging. As you said, having a legend like that..when he says something, you’re gonna listen.”

Fikayo Tomori

Maldini has been a key part of the rebuilding process at Milan. 

But the turbulence off the pitch had affected the team’s performances on it. 

For seven years they failed to qualify for the Champions League until finally returning to the competition this year.  

Yes, across the decades, Milan are giants in Europe, but in the last few years they’ve been minnows.  

Serie A pundit Gab Marcotti thinks people need to move on from the Milan of old.

“And people are bringing up… I mean I think it was Frank… oh but the Milan teams…the great Milan teams of the ‘90s. You know… those are the old days! The thing about the old days is they are the old days! That’s a different Milan… it’s a different world! It’s a different landscape now. Stop judging them against that.”


But that’s wishful thinking. When did football fans stop clinging to nostalgia? They want the glory days to come back.  

And that’s where Paolo Maldini comes in.  

Could there be a more inspirational figure?

Because when it comes to knowing what it feels like to pull on that famous red and black shirt, he has no equal.  

Of course, helping to manage a club is different to playing for it, but you can see why the fans look to him in the quest to rebuild the club and restore its reputation.

Today’s episode was written by Chloe Beresford, and produced by Imy Harper.