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Massimiliano Allegri: The Man Behind the Legend


Stubborn. Determined. Effective? These are three words that perhaps best describe the enigma that is Massimiliano Allegri. Love him or hate him, on paper, he is incredibly successful. People can argue whether or not those accomplishments are truly his, or perhaps he has simply been in the right place at the right time. But either way, he is at least part genius for being poised for such success. And geniuses are not always popular. Despite having one more year on his contract as manager of AC Milan, Sunday’s match will be key to determine whether or not he will stay on for one more year, or perhaps even be offered an extension. Ahead of this crucial fixture, here is a little more background on the life and character of this polarizing man.

He's like the average student who wins the National Spelling Bee or Science Fair
Hailing from Livorno, Allegri’s footballing career could be described as relatively mediocre. He played mainly in the lower leagues until the age of 24, when he signed for Pescara. That season, 1991-92, saw Pescara promoted to Serie A. The following season, despite Pescara being relegated back to Serie B in last place, Allegri was a tremendous asset to the club, scoring 12 goals from midfield, and putting him in a very elite group of midfielders to ever do that in Serie A. You could argue that he was to Pescara what Nocerino was to Milan his first season.

The next season, he went to Cagliari, where he played for two seasons, then two seasons at Perugia, then six months at Padova, six months at Napoli, and back to Pescara for a couple of years. He finished his playing career at lower table clubs Pistoiese and Aglianese, retiring in 2003. It is curious to note, however, that he was convicted of matchfixing relating to a Coppa Italia match in 2000, and served a one year ban for this in 2001.

A mostly mediocre player, he left his mark on Serie A at Pescara with 12 goals from midfield

His coaching career began in Serie C2 with the club he ended his playing career with, Aglianese. From there he moved to Serie C2 side Grosseto, but was sacked early on in the season. He chose to go to Udinese as a coaching staff member rather than head coach, but earned a 3 month ban because he moved to Udinese while technically still under contract with Grosseto. I don’t know if these bans of his were due to a character flaw, if he felt he was above the laws, or if he was simply unlucky. But it is only a minority of players or coaches who actually earn and end up serving bans, and he has managed to accomplish it as a player and a coach.

His coaching career took off with Sassuolo, where he led the Serie C1 side to their first promotion to Serie B, despite serving that three month ban during the middle of the 2007-08 season. It is of note that Sassuolo are currently poised to promote to Serie A for the first time this next season, and their owner, Squinzi, recently had glowing things to say about Allegri, including that he hopes the club can do well in Serie A and that Allegri could once again manage them.

A very young Allegri shown here at his first job as a manager for Aglianese

His success at Sassuolo earned the attention of Serie A side Cagliari, where Allegri would earn the peer-voted Panchina d’oro, or golden bench award, which is given to the best Serie A manager each year. He brought the team to a very impressive 9th place finish that season, with a relatively mediocre team. His second season saw Cagliari at a very respectable 12th place in Serie A, yet Allegri was suddenly and quite inexplicably sacked in April. This, of course, led to his availability for Milan, who quickly snatched him up post season.

From Serie C2 to Scudetto with Milan in only 7 years. Genius?

It is unnecessary to tell you what happened next. With an incredible roster of star players, he led Milan to a fairly convincing Scudetto run his very first season at a big club. Some say there was little competition, and that it was due to the players, not him. Whatever you believe about that, he has a Scudetto on his bio. And a second place finish the following year, despite an Injury Armageddon™ the likes of which is rarely seen. And if he plays his cards right on Sunday, he could have a third place finish on a season where the rug was almost literally pulled out from under his feet in terms of quality of players and the sheer number of players changing, too. All of this under intense criticism and scrutiny from the lowest of fans all the way up to the President of the club, a fate perhaps worse than being sacked.

Appropriate for his Juventus fan roots, this is his old lady, or ex-wife

In his personal life, he was married and has a daughter, Valentina, whom he loves to spend time with. He and his wife are divorced, so he upgraded to a 24 year-old ex-Playmate, Gloria Patrizi, who is almost half his age (he is 45 years old) and barely older than his daughter. I told you he is a genius.

The upgrade: She's young enough to be his daughter, and an ex-Playmate, too. Genius.

Polarizing, uncharismatic, and incredibly lucky. He has made the most of what he has been given, and yet is still unconvincing to many. Personally, I applaud his determination and work ethic. It seems that given his track record of mediocrity and brushes with scandal, he is to be given credit for earning his way to a club like AC Milan. But his stubbornness seems almost more flaw than strength. What is almost unnerving, however, is how effective he has been, or at least all of his teams have been under his watch. More unnerving is how ridiculously close to even more success he has been, and what his slow season starts and stuttering finishes could have been. Whatever your thoughts about him, there is more than coincidence at work here. But how much of it is him being effective and how much of it is luck and/or a talent for surrounding himself with the right people?

The one constant love of his life, his daughter, Valentina

Recently, there was an “Allegri by the Numbers” set of stats produced by Opta. At 60% win percentage, Allegri has the second-best win percentage in Milan’s Serie A history. He is currently the second-longest serving manager in Serie A, behind Mazzarri of Napoli, and he is the third youngest manager to win Serie A since the three-point win scoring system was introduced, having won the Scudetto at age 43. All incredible accomplishments, and for anyone who has ever been subjected to his press conferences or been frustrated by his incredibly calm demeanor following an important loss or draw, it may be even more incredible to see him etched into the record books of both Milan and Serie A.

A parody of the Dos Equis beer commercials, Allegri is The Most Interesting Coach in the World

As a Milan fan, I am losing sleep anticipating the results of Sunday’s match. And I am also watching Allegri’s every move, facial expression, and reading every quote. As a Serie A manager, he earns such scrutiny a part of his job description. But I am also quite curious to see what becomes of him in the long run. He said last year that he only wanted to coach until age 55 because of the stress, but that he would also love to coach the national team. Will his determination take him to his goals? Or will his character flaws keep him from his dreams? What will statistics say about a man for whom there really are no words? Will his accomplishments be credited to his effectiveness, or will they be given the asterisk of luck or association? How he manages this game on Sunday could have a lot to do with those answers. Or it might not. Love him or hate him, he is fast becoming a legend.


This post inspired by the music of Ludo’s “Love Me Dead”

Our next match is
Siena vs. Milan
Sunday, May 19 • 20:45 CEST (2:45 EDT)