AC Milan v Manchester United on US tour is as close to Champions League glory days as Serie A giants can dream of

Seven-time European champions have not played in the tournament since 2014 and shows English Premier League club’s fans how bad it could be

PUBLISHED : Thursday, 26 July, 2018, 9:55am
UPDATED : Thursday, 26 July, 2018, 10:11am

There were 37 minutes to kick-off when Gennaro Gattuso charged alone onto San Siro’s wet turf, his presence nearly lifting the space-age roof in one of football’s most iconic venues, sparking a roar from 70,000.

Back from injury, the raffish midfielder appealed for support, his message clear: we’re up for this and you’d better be. It was the 2007 Champions League semi-final second leg, AC Milan against Manchester United. Two giants of world football slugging it out in one of football’s biggest games.

Milan, with football’s best player Kaka, had lost the first leg 3-2 at Old Trafford but United’s players admitted in private that Kaka had killed them.

Going into the second leg, United were carrying injuries and missing key players, but Sir Alex Ferguson saw things differently. He felt United had let Kaka play in the first leg and expected better.

But, despite Ferguson’s optimism, United lost 3-0 and were so outclassed by Kaka and Gattuso that the Italian media questioned the pre-match buzz around Cristiano Ronaldo and Wayne Rooney.

Milan went to the final and Kaka surged ahead of Cristiano Ronaldo to become favourite to win the Ballon d’Or.

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Lionel Messi came third, Milan’s Andrea Pirlo fifth. Milan’s Filippo Inzaghi, Paulo Maldini, Clarence Seedorf and Gattuso all received votes. It was a team of stars, with Kaka the stand out.

“The 2005 Milan side were better,” states former Liverpool captain Jamie Carragher. “Their midfield was the key: Pirlo, Gattuso, Seedorf and Kaka. I think the secret to their success was Ancelotti changing the system to a midfield diamond to suit the players. He’d been brought up on the 4-4-2 of Arrigo Sacchi.”

“We couldn’t believe we were there,” explains Carragher of the 2005 Champions League final, “then what happened happened.”

Liverpool famously came from 3-0 down at half-time in Istanbul to eventually win on penalties.

“That 2005 final was my worst nightmare.” Milan fan Andrea Landi, who is preparing to see his team tonight in Los Angeles has painful memories. “Istanbul was unthinkable, the apocalypse. We were the best team playing the most dominating, beautiful football and we led 3-0. I was texting my Juventus-supporting friends at half time saying ‘keep your Serie A, this is how you win the Champions League.’ I thought it would be 7-0.”

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But Carragher thinks Liverpool should have done better in 2007. “Kaka was much improved from 2005, but nobody else was and we actually looked at it as a major opportunity missed. We went into the final confident. They didn’t have Crespo and Shevchenko up front any more.”

Landi and the Milan supporters were also confident. “Inzaghi was on fire. He had a point to prove after being left out in Istanbul 2005. He scored twice in Athens.”

In the Athens final, Milan’s third final in five years, Carlo Ancelotti’s side beat Liverpool to avenge their 2005 defeat and win a seventh European Cup. To this day, only Real Madrid have won more.

In the last five seasons Milan have finished no higher than sixth and as low as tenth in Serie A. Milan’s average home crowd was 50,000 in the late noughties; by 2015 it had dropped to 36,000 in the 80,000 capacity San Siro.

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Milan were caught in a storm. The rise of the English Premier League knocked Serie A off it’s perch as football’s richest league, while the 2008 financial crisis hit southern Europe hard, including Italian club owners. High tax rates meant that Italy continued to lose players, while Spain offered a preferential tax rate, the so-called Beckham law, to attract premium talent.

Most Italian clubs didn’t own their own stadiums and couldn’t exploit their potential, while merchandising, a growth area in England, lagged behind with fake replica shirts on sale outside stadiums at a quarter of the cost of those being sold by the club.

Hooliganism didn’t help crowds across Italy, though the country remains one of the greatest places to experience a febrile atmosphere.

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Even before their 2007 triumph, Milan’s halo had started to slip. Calciopoli, the match- fixing scandal exposed in 2006, shook Italian football. Juventus, the most powerful club in Italy, were demoted to Serie B and Milan were deducted 15 points, later reduced to eight.

Today, Leicester City have a higher annual revenue than both Milan giants. AC Milan, an ever present in football’s top 20 richest clubs and third in the world in the mid noughties, dropped out of the top 20 in 2017. Serie A’s domestic TV deal is less than half that of England’s Premier League and Milan haven’t enjoyed the Champions League riches as they don’t play in it.

Silvio Berlusconi, Milan’s long time owner, sold the club in 2017. Li Yonghong, a little known Chinese businessman, fronted the Rossoneri Sport Investments Luxembourg consortium which took over. Milan fans were hopeful and ticket sales surged as new players including Leonardo Bonucci arrived.

The optimism proved false as Milan finished 6th last season, while the new owners went to an American private equity fund to raise finance. That equity fund now owns AC Milan.

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Tonight, Milan play Manchester United in a friendly in Los Angeles. United, still one of the two richest clubs on the planet, have also fallen since they were European champions in 2008. Milan, the world’s best team the previous year, have declined much further, but at least they still have Gattuso on the payroll. He’s their coach, at least for the time being, in the fast moving soap opera of AC Milan.