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What If AC Milan Began Rebuilding Their Ageing Squad After 2007?

Players in. Players Out.

Soccer - Barclays Premier League - Manchester City v Chelsea - City of Manchester Stadium Photo by Dave Thompson/PA Images via Getty Images

Many would argue that in 2007, AC Milan had reached the summit of European football, winning what has been their 7th and last Champions League in the club’s long history.

In 2007 Milan already had an ageing squad that was ignored due to the brilliance of the talented senior players and their experience in handling knockout games. It is worth remembering that Milan finished the league in 4th place, a huge margin away from top place Inter who finished an incredible 36 points, ahead of Milan - note that they were docked 8 points due to the Calciopoli scandal.

The team had always maintained that the Champions League was the main challenge, but 36 points behind your city rivals is something that should have been addressed more, considering the league is when you see how strong over a long season your team can perform. Milan had talent, all across the pitch, but it was ageing and unable to perform as well in the league as it managed to do in knockouts at the highest levels.

What Transfers Happened After The UCL Win?

Players In

Alexandre Pato joined the club for 24 million from Internacional.

Emerson joined the club for 5 million from Real Madrid.

What Players Moved Around The Market At The Time?


Arjen Robben for 36 million from Chelsea to Real Madrid

Wesley Sneijder for 27 million from Ajax to Real Madrid

Franck Ribery for 25 million from Marseille to Bayern Munich

Thierry Henry for 24 million from Arsenal to Barcelona

Carlos Tevez for 18 million from West Ham to Manchester United

Gareth Bale for 5 million from Southampton to Tottenham Hotspur

Fernando Torres for an Undisclosed fee from Atlético Madrid to Liverpool

Kevin Prince Boateng for an Undisclosed fee from Hertha Berlin to Tottenham Hotspur


Robinho for 32 Million from Real Madrid to Manchester City

Dimitar Berbatov 30 million from Tottenham Hotspur to Manchester United

Gerard Pique for an Undisclosed fee from Manchester United to Barcelona

Branislav Ivanovic for 9 million from Lokomotiv Moscow to Chelsea

Who Could Have Milan Sold To Generate Revenue?

A.C Milan Squad;

Dida, Cafu, Maldini, Kaladze, Costacurta, Oliveria, Gattuso, Inzaghi, Seedorf, Gilardino, Nesta, Borriello, Kalac, Simic, Jankulovski, Favalli, Gourcuff, Pirlo, Kaka, Ambrosini, Grimi, Bonera, Storari, Serginho, Guerci, Fiori, Antonelli, Brocchi, Di Gennaro, Bottini, Darmian, Lunati, Oddo, Ronaldo

For any Milan fan, selling any of the above players for sentimental value seems and feels wrong. It’s not surprising that in the end, this stopped the team from rejuvenating and fixing huge problems that all of the club must have understood were coming. Everyone is scared of too much change, and Milan didn’t change anywhere near enough when the time was right. These changes will leave Milan with a hollow shell of a squad when the legends left the squad between 2008 and 2012. Each year, Milan lost at least two or three core players with no replacements leading to the eventual decline of the club. The likes of Maldini, Cafu, Nesta, Seedorf, Pirlo and Inzaghi have not been sufficiently replaced to date. This begins with a lack of proactive action after the Champions League victory of 2007.

What If Galliani thought differently? Who could we have sold?


Alberto Gilardino

He had a great season scoring 12 goals in the league in 2007, but really didn’t manage to make the starting 11 after this losing form, and falling behind a young star in Pato in the following seasons. Bought for 25 million.

Sell: 20 million

Andrea Pirlo

A much harder transfer for Milan fans to let happen given his importance to the team, in many areas, however looking back I feel that Pirlo leaving in 2007 to Chelsea or Madrid would have been the best scenario for both sides. Pirlo was one of the worlds best, however It would have been better to lose him to a foreign side such as Chelsea or Real Madrid than Juventus in 2011 on a free transfer. Milan should never let him go there.

Sell: 30 million


Dida was a top goalkeeper for Milan proving to be a wonderful addition to the team, however he was always capable of a mistake, and after 2007 winning the top honours in football, it would have been a great time to change, allowing Abbiati to fill that goal for the following years.

Sell: 10 million

Yoann Gourcuff

Signed to be the next Kaka, or Zidane the french midfielder never found that level. Given his massive promise at the time, Milan could have capitalised on the hype and made some sort of profit on him.

Sell: 10 million


Manchester City were the first club to ask for the talisman, offering 100 million and very serious about taking the Milan star. If Kaka did want to leave, and Milan were serious about rebuilding a team, 100 million in 2007 would have been the catalyst in changing the club from senior to prime.

Sell: 100 million

Keep Rather than Loan

Luca Antonini

A young hardworking full-back who always gave his best, Antonini could have been given an earlier start to his A.C Milan career. In 2008 he came back and was a strong part of both teams were the team finished champions 2010/11 and then second place in the 11/12 season. For under 3 million and on a great wage, the club should have been focused on our internal youngest rather than ageing giants such as Zambrotta in further years.

Christian Abbiati

Initially brought back 2 years after the 2007 CL final, Abbiati would have been the perfect replacement for Dida, already in our hands, and on a lower wage than the Brazilian. Unfortunately, he was loaned to Atlético Madrid, where he became the Number 1 keeper instead. During our Scudetto victory and other high ranking finishes, he was a reliable man between the sticks.

Ignazio Abate

Energy, pace, and strength are the three words most would use to describe Abate. With monstrous games denying C. Ronaldo and other pacy wingers used to breezing past full-backs, Abate never allowed it. He was another young player in the group, worthy of being given an earlier chance, however, needed to wait until the 2009/10 season to get it, becoming the teams starting right back, and later captaining the squad.

Available revenue from sales: 170 million

Alternatively, I would have invested in:

Carlos Tevez

Price: 30 Million

(I believe in total Manchester United spent this fee according to fees listed) With 18 million and 12 million being given to multiple parties. We know how deadly Tevez was in Turin, and also that Galliani had every chance to sign him in the years following 2007 including the shamble of an approach in 2013.

Tevez had everything fans and winning teams need, with work rate, skill, and the ability to score and assist.

Gareth Bale

Price : 5 million

Capable of covering the entire left side, this would have been a wonderful signing for utility and youth in the squad at the time. Even if Bale never became the wide attackman he is today, as a player with pace and power, he would have added a much-needed freshness to the squad.

Kevin Prince Boateng

Price: 5 million

We all got to see his best and worst, however, as an impact player or starter, this would have been another smart signing for cheap. He was already receiving some hype and could have developed further behind some veterans.


Price: 32 million

Robinho did play for the club, and was always capable of winning a game. Picking him up years earlier to link with Pato and Tezez would have completed the triangle of power, pace and skill going forward with years ahead. Also with Galliani’s ties to Madrid, an even easier deal than what Man City attempted, would surely have happened.

Branislav Ivanovic

Price: 9 million

A strong dedicated defender who works hard and has since played all across the back 4 for Chelsea, this would have been just the type of signing to fill in the gaps while changing Milan's Back 4.

Expenditure: 81 million

Milan’s Actual Starting XI


Cafu, Nesta, Kaladze, Maldini

Gattuso, Pirlo, Seedorf


Gillardino, Pato

Milan’s Alternative Starting XI


Abate, Nesta, Maldini, Ivanovic

Gattuso, Ambrosini, Seedorf


Pato Tevez

4–3–1–2 Formation


4–3–3 Formation

From the bench, the team would have had a wide selection of experience and youth including; Inzaghi, Bale, Antonini, Bonera, Brocchi, Ronaldo (R9) Borriello, and Kevin Prince Boateng. This would have allowed the older legs to be used in games when they didn’t need to play 90 minutes during the week in Serie A matches. It also guaranteed that moving forward, the starting 11 would continue to improve with the talent of players growing and settling into the team moving from the bench to the first eleven.

With strikers Pato and Tevez, working with Robinho and Seedorf providing the support, the attack would have been deadly. 2 holding midfielders with a high defensive work rate would have finished off the squad. The team would have been in a great position to then add in Thiago Silva, and other defenders over the next 2 or 3 years to help ease Nesta and Maldini into retirement.

The squad had a number of ageing players who likely would have been hard to move on for a fee, however, limiting the contracts and easing in the youthful players would have been the best option looking back. The squad had many talented youth players available, but time and time again were overlooked to make the squad.

In 2007, what players would you have sold? Which players would you have brought in?

Let us know in the comments below!