Soccer expert (and lifelong AC Milan fan) Samantha Savarino breaks down the FC Barcelona-AC Milan Champions League Round of 16 matchup.
Even for a die hard Milanista like myself, it is hard to imagine not seeing F.C. Barcelona move on to the quarterfinals of the UEFA Champions League once they are done with this tie with AC Milan. From their surgically precise short passing game to Lionel Messi to its predigree in Champions League play to Lionel Messi (yes, twice), Barça by far is the team to beat.
I propose to you how the Rossoneri can do exactly that.
First, we must concede that no matter what you do, there is no stopping Messi. His four Ballon d’Or awards in a row are a record, and a fifth almost surely on his way after this campaign. Many teams try to play a zonal marking system to limit Messi from being a creator, but in my mind, you have to choke him off at every pass and man-mark him and not let him be a creator nor a threat to score. As a matter-of-fact, just don’t let him receive the ball, period. 
That would be little problem for Milan circa 1990, with the likes of Franco Baresi or Paolo Maldini being so good at being an opponent’s shadow from their defender/libero positions. Milan will probably go zonal with Messi, which will drive me crazy, but it is encouraging that the Milan back line is playing much like the quartets I know from the past, with Philippe Mexes being a star during the group stage and Cristian Zapata being much for comfortable back in Serie A than his short time in La Liga with Villarreal. Obviously, you still have many others to contend with on Barça (Xavi, Iniesta, Fabregas, etc.), but cutting off Messi might be their best bet. It would not be the full-on catenaccio defense that drives opponents, and even supporters, crazy, but this is Champions League survival at stake.
Now when Milan has the ball…well, they have to have it first.
This is where Kevin-Prince Boateng will probably be Milan’s most important player in the two legs. He likes to attack, and has scored some amazing goals, including in Champions League. In this game, however, he must channel a former Milan great Andrea Pirlo, the reserve midfielder that is able to spring passes forward from the defensive half to give Milan the rare scoring opportunities it is going to get. I have yet to see new striker M’Baye Niang play, but I hear rave reviews and he and Stephan El Shaarawy must stay forward and be ready to take advantage when those long balls are played to them and Milan are able to play the contropiede (counterattack). 
And as much as Barça is famous for its tiki-taka, Milan is not afraid to incorporate their triangular passing into these contests. But instead of the passing being used to eventually open up gaps and exploit a lack of discipline in defense, Milan may use it as strategy to stall, if it has the result it desires. It is not uncommon for that style to frustrate even its own supporters in the San Siro, as they’d rather see the ploy be used for more of an offensive nature than stalling, to the point that the fans’ intolerance for it may cause the team to stop. It is effective, and it would also behoove Milan to try to use these short passes against the masters of it, to keep them off balance.
So in short, man-marking on Messi, turning defense into offense with the long balls to the forwards on counterattacks, have a more offensive attitude to make Barça play defense and convert when you can. It would not surprise me if that style of plays catches Barcelona by surprise, and Milan can nick a goal before the Catalan giants are even settled into the game (think Alexandre Pato in the group stage a couple of seasons ago). If only games were played on paper, right?
Lastly, and this is more visceral than strategic, Milan has to play like they are worthy of the shirts they are wearing. Players in the past wearing those red-and-whites have won seven European Cups and took pride in not disappointing the faithful at the San Siro. It was worrying at the beginning of the Serie A season when the relative no-name Milan was struggling in the middle of the pack for the first two months. Just one loss in its last 13 games, and Milan are coming into today’s game playing better than anyone in Italy, including the defending champions (and current leaders) Juventus. The crowd, their history and current form should count for something. And it would, if they were not playing Barcelona.
I would not be surprised if Barcelona were to win 2-1 or 3-1, though I sincerely hope that Milan will at least tie the game and force the return match to be more than a formality at the Camp Nou!
