Milan have had a rather disappointing campaign. Are Allegri and the squad good enough to send the Rossoneri back to the pinnacle of Europe?

The defeat to Inter Sunday night in the Derby della Madonnina was the spoiled icing on an unsavory cake of a season for Milan. The Rossoneri failed to defend the Scudetto, went out in the quarterfinals of the Champions League, and were knocked out of the Coppa Italia by hated rivals Juventus. Add to this two derby defeats and the season cannot be considered anything but a major disappointment. Granted, Milan had an injury list comparable to Joey Barton's rap sheet. But despite the lengthy absences of such crucial players as Antonio Cassano, Thiago Silva, and Kevin-Prince Boateng, one must wonder if Massimiliano Allegri could have done better.  In addition, There are doubts not just about Allegri's capabilities as a top-tier manager, but surrounding the squad as a whole.  Despite last year's Scudetto winning campaign, the current Milan side lack the dynamism, creativity, and attacking intent of Ancelotti's Milan that was a European powerhouse half a decade ago.

From 2002-03 until 2006-07 Milan failed to reach the semifinals of the Champions League just once in 2004, going out in the quarterfinals to an inspired Deportivo La Coruña. They won the European Cup twice in that span and if it wasn't for two infamous collapses, the 6 minutes from hell in Istanbul and the aforementioned disaster at the Riazor against Deportivo, they may have well have added to that tally. But since the vendetta against Liverpool in Athens Milan have failed to return to the pinnacle of Europe. Their most successful campaign since 2007 in Europe has been the current one in which they reached the quarterfinals of the competition, only to be dismissed by a vastly superior Barcelona outfit. In that time they have suffered through the ignominy of a UEFA Cup exit at the hands of Werder Bremen, a side that finished 10th in the Bundesliga that season. They have been humiliated by Manchester United and failed to score in 120 minutes against Spurs. There have been some bright spots such as the victory over Real Madrid at the Bernabéu and the 4-0 defeat of Arsenal, but Milan have fallen from the elite of Europe. Wednesday nights at the San Siro just do not feel as magical and mystical as they did under Carlo Ancelotti.

What went wrong? To start, one can simply take a look at the team sheets. Take a look at the squad that the Rossoneri fielded in the 2005 defeat to Liverpool (despite the freakish defeat this was arguably Carlo's best Milan squad):

Compare that with the starting eleven that used in the 4-0 over Arsenal, without a doubt Milan's best European performance in the Allegri era:

It does not take a football expert to notice the vast gap in quality between the two sides, especially in the midfield. Whereas Carlo's Milan featured a wealth of creative talent and attack-minded players, Allegri prefers to pack the midfield with defensive, hard-working ball winners. There is nothing inherently wrong with this approach, but it does not do justice to Milan's European pedigree and historical successes in Europe.

The decline in quality of the squad cannot be explained without an analysis of Milan's current transfer policy. There have been some high-profile acquisitions in the post-Calciopoli era. Ronaldinho, Ibrahimovic, Robinho, and Cassano are all highly-rated, class players who have made a significant impact in European football. But for none of those purchases did Milan have to beat out competition from other clubs. In fact, all four were to a certain extent pushed out of their previous sides. Both Ronaldinho and Ibra did not feature in Pep Guardiola's plans and were offloaded to the San Siro. Cassano had a falling out with the Sampdoria management and Galliani moved quickly to get a deal. Robinho fell down the Manchester City pecking order and was sold to Milan for a much lower price than the Eastlands club had paid to acquire him from Madrid. That is not to say that these players are not Milan quality; that is an entirely different debate altogether. But it is a worrying trend that, with the two notable exceptions of Thiago Silva and Alexandre Pato, Milan's most important transfers in recent years have not been highly valued, sought after players. Instead, they have been cut-rate acquisitions of players no longer needed by their clubs, or cheap, last-minute squad additions.

Back to Allegri. It would be unfair to criticize the manager for Milan's transfer policy because it is unclear just how much say he has in it. But there is much evidence that suggests that Allegri is not up to the challenge of managing a team of the stature of Milan. In his first season in charge Allegri gradually phased Andrea Pirlo out of the starting eleven. The Italian international and World Cup winner started just 12 matches, his lowest total since his first season with the Rossoneri. He was forced to play on the left instead of his favored deep lying playmaker position in the center of the midfield. Marginalized from the squad, Pirlo chose not to extend his contract and signed with Juventus. “AC Milan have lost a fantastic player,” remarked Pep Guardiola. How right he was. At Juventus Pirlo has rediscovered his form and inspired the Bianconeri to their first post-Serie B stint Scudetto, leading Serie A with 13 assists. One could make the argument that Pirlo had lost his motivation at the San Siro and needed a fresh challenge, as Allegri claimed earlier this year. But it is hard to believe that in his current form, Pirlo would not have been an asset to Milan this season.

Pirlo has rediscovered his form at Juve

Letting Pirlo go would not have been such a terrible decision had Allegri had a plan for life without him. But Milan failed to bring in any new midfielders in the off-season that could offset the loss  of the element of creativity and invention in the middle of the pitch. The closest Pirloesque player acquired over the summer was Alberto Aquilani, a notoriously injury-prone failure that has failed to consistently break into the starting 11 at both Liverpool and Juventus. Nocerino has been a pleasant surprise but, despite his impressive (and totally unexpected) goal tally he does not supply the creativity Milan so desperately need. Tactically, Allegri's 4-3-1-2 is overly reliant on Ibrahimovic's spontaneous ingenuity. When the Swede has an off day, Milan struggle to score. Milan's predictable set up is effective at breaking down provincial Serie A sides, but the top teams both in Europe and Italy have got it figured out. This season Milan's record against the top five sides in Serie A has been a pitiful one victory, four draws, and five defeats. In the Champions League knockout round in the past two seasons it's 1-2-3.

Milan have had an inordinate amount of injuries this season. Questions must be asked of the once-lauded Milan Lab, who have become a laughingstock of Europe. Juventus can thank Pirlo, Conte, and Milan Lab for the Scudetto, as the joke goes. But Allegri has done nothing to help the situation. If anything, he has exacerbated the crisis. Playing a not-fully fit Thiago Silva against Roma with the crucial Champions League match against Barcelona around the corner, after the defender had gone 120 minutes in a mid-week Coppa Italia clash, was not a responsible decision. Silva went off injured after 10 minutes and has yet to return.

 If Milan want to return to the pinnacle of Europe significant changes must be made this summer. There have been persistent rumors linking Thiago Silva to a move to the Camp Nou in exchange for Seydou Keita plus cash. Selling their top asset and one of the world's greatest defenders would confirm that Milan are no longer among the elite of Europe. It would also continue the trend of settling for players no longer wanted by other sides. Ibrahimovic has also recently come out and said “There was a project of a great Milan, we will see if they want to pursue it” (link in Italian).  A clear indication from the most important player in the squad that Milan need investment if they want to keep their best players. With reports that Mourinho is desparately trying to convince Ibra to join him in Madrid and considering their close relationship while the Portuguese manager was at Inter, a transfer request by the Swede is not unthinkable. I will not speculate here as to who will join in the summer. But this side is simply not good enough to be ranked among the top teams in Europe. There is a complete lack of creativity in the midfield and the manager has not demonstrated that he can perform on the big stage. Less than a decade ago Milan were the powerhouse of Europe, a Champions League favorite year in year out. Silvio Berlusconi will need to whip out his checkbook this summer if he wants to see his Rossoneri win the cup with big years in the near future.