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Milan seek first silverware since 2011, but Juventus stand in their path in Coppa Italia final

Carlo Ancelotti became a grandfather last week. When word reached the ultras in Milan’s Curva Sud, they made sure a special banner congratulating their former condottiero was prepared, unfurling it during Saturday’s comfortable win against Hellas Verona. 

“Andrea will be a Milanista even though his father is Neapolitan,” Ancelotti assured Milan TV on Monday. “It’ll be a fight between mozzarella and parmesan. But I am convinced he will prefer parmesan.” 

It’s almost a decade since Ancelotti left the Rossoneri, but the affection in which he’s held remains undiminished in large part because of his association with the last grande Milan. He’ll be supporting his old club in Wednesday’s Coppa Italia final against another former employer, Juventus. “I’m going to watch it with a friend of mine who’s a chef here in Canada. He’s a big Milan supporter and we’ll be putting our Milan shirts on,” Ancelotti promised. 

The memories will come flooding back: for a brief moment 2018 might feel like 2003 again. Has it really been 15 years since Ancelotti won this trophy, finishing the job in a two-legged final against Fabio Capello’s Roma in the heady days that followed Milan’s Champions League triumph at Old Trafford? 

Snarling around midfield in both those successes was current manager Rino Gattuso. What he would give to have the calibre of players Milan had on the bench in that cup final; Sandro Nesta, Andrea Pirlo, Andriy Shevchenko… Even flops like Rivaldo turned out decisive, which in itself is enough to give you pause - yes, Rivaldo was considered a flop.

Gattuso won eight finals as a player. Now it’s up to him to emerge victorious from his first as Milan manager. It would be the first of the post-Berlusconi era, which explains why the mysterious Li Yonghong has suddenly decided to put in a rare appearance on Italian soil. Milan are no closer to refinancing their debt, UEFA are deliberating what sanctions to take and the repayments on last year’s summer spending spree are due, provoking no shortage of concern. But for now all attention is on Wednesday’s final at the Olimpico.

Gattuso says it should be for Milan what the 2006 World Cup final was to him. It’s not the first time he has given a big game this kind of billing. In fact it’s getting a bit repetitive. But Gattuso’s exchanges with the media are never dull. You can see why his players want to play for him. 

In Tuesday’s press conference Gattuso spoke brilliantly about Milan’s opponents. Throughout the answer, though, you couldn’t help but feel he was describing what he is seeking to achieve with his own team. “As a player Juve always gave me the sensation that they were a team with a great mentality, a great sense of belonging.” he said, “Every player seemed proud to pull on the shirt. They had the bit between their teeth. It always fascinates me; the discipline, the togetherness. They know what they want to do and are ready for battle.” 

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Which is probably just as well. Because Juventus know they’re in for one on Wednesday night. “Looking at the history between the two sides, I quickly realised that you never start favourites against Milan,” Gigi Buffon said. “We’ve played four finals with Milan. They’ve won two on penalties, we won one in extra time and another on penalties. It’s hard to imagine the game being settled in 90 minutes.” 

And it's worth remembering this group of Milan players beat Juventus in the Super Cup in Doha 18 months ago. It was the first piece of silverware the team won since Allegri’s dismissal and the last of Berlusconi’s time as owner. March’s game at the Allianz Stadium was also very competitive with Milan leaving Turin with their heads held high despite a 3-1 defeat. The Rossoneri showed character, coming back from behind to put the champions on the ropes for a while. Leonardo Bonucci scored on his return to his former club and didn’t think twice about celebrating. Hakan Calhanoglu hit the bar and Andre Silva should perhaps have scored a header, before Massimiliano Allegri intervened and changed the game from the bench. 

A theme started that night and has recurred ever since. Douglas Costa and Juan Cuadrado impacting games in devastating ways as second-half substitutes. It’s arguably been the difference in Juventus winning a seventh straight Scudetto. Their freshness, quick thinking and fleet of foot has contrasted with the tiredness that has characterised both teams over the last few weeks. 

Milan, we shouldn’t forget, started the season back in July, needing four games just to make the Europa League group stages. Blowback is to be expected, particularly after how hard they chased Champions League football this spring. Juve have had it tough mentally and physically too. As Allegri said after the defeat by Napoli, when the Old Lady’s crown looked to be genuinely slipping, his team has played more or less every game across three competitions for four years. In fact, their elimination at the hands of Bayern in 2016 and Real Madrid this season mean they are only eight short of the maximum.  

“It’s definitely been an emotionally complicated year,” Buffon said. “That’s undeniable.” Italy’s failure to qualify for the World Cup in November, Juventus’ stoppage-time exit from the Champions League at the Bernabeu and Napoli pushing them harder than anyone in seven years has drained the team’s leaders. Bizarrely, this is Buffon’s first Coppa Italia final since 1999. It’s also likely to be his last. That’s why the recent tradition of his back-up starting in the Cup is being broken. 

Juventus are on the brink of their fourth consecutive double. To some that’s boring. To others it’s a remarkable demonstration of consistency when you consider how even the best teams are never more than one bad transfer window away from everything unravelling. “We need to play a perfect game,” Bonucci said.

Milan showed in March they are capable of making Juve sweat. Excellent for 70 minutes, lasting longer is the issue and it’s interesting Gattuso chose to make an issue of this on Sunday despite Milan registering a comfortable win against Hellas. He won’t tolerate it on Wednesday. Two routes into Europe are all that's left to Milan. Neither is easy. It’s either beat Juventus in the Cup final or take down Atalanta and Fiorentina in what effectively amount to Europa League play-offs.

The difficulty rating is high; the pressure mounting. Gattuso told an anecdote about taking his team-mates up on a dare to devour a grass snake to help ease some of the tension before the 2007 Champions League semi-final against Manchester United. He might need to resort to something similar in the warm-up at the Olimpico. 

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