The Question: Should AC Milan Have Hired Marco Giampaolo over Vincenzo Montella?

For AC Milan, this Friday night will present a meeting of what is and what could have been.

Over the summer, when discussions were ongoing as to who would be appointed Milan head coach following the departure of Cristian Brocchi, two names were particularly prominent amid the constant speculation.

One of the names mentioned was Vincenzo Montella, formerly of Fiorentina and most recently Sampdoria. The other was Marco Giampaolo, who enjoyed a successful 2015-16 season in charge of Empoli.

Ultimately, Montella would be appointed Milan coach on June 28, and within a week of that announcement, Giampaolo was hired as his replacement in the Sampdoria dugout.  

The pair will go head-to-head on Friday when their two new teams face each other at the Stadio Luigi Ferraris in what promises to be an intriguing battle of respected tacticians as well as an early barometer for what lies ahead.

The match may also provide further clarification, if not a comprehensive answer, regarding the question: Did Milan make the correct decision in appointing Montella over Giampaolo?

The start to this season has not been a positive one for the Rossoneri. An opening day 3-2 win over Torino came courtesy of a last-gasp penalty save from Gianluigi Donnarumma, though the 4-2 defeat away to Napoli only reinforced the gulf in class between Milan and Serie A’s finest.

And following the international break, a 1-0 home loss to Udinese acted as a serious wakeup call to Montella and his players. With two defeats from three games, seven goals conceded and three red cards, the new coach has endured an inauspicious beginning to his tenure.

By way of contrast, Giampaolo has enjoyed his opening three league games in charge of Sampdoria, picking up two wins, one of which came away to his old club Empoli. His sole competitive defeat thus far, 3-2 away to Roma last Sunday, was an understandable one.

Very early in the season, but Marco Giampaolo is doing a good job in his first season as Sampdoria’s coach.

— Raffaele (@ItalianoCalcio) September 11, 2016

@TheCalcioGuy Sampdoria are pressing and fighting like they are playing for the Champions League. Sensational stuff from Giampaolo’s men

— Marco Messina (@Marcocalcio22) September 11, 2016

Perhaps what has been most impressive about his start to life with the Genovese club has been the speed with which he has implemented his football philosophy, something that was on show last term as he guided Empoli to an impressive 10th-place finish in Serie A.

“Giampaolo’s playing style is quite unique,” said Tom Payne, an analyst for Spielverlagerung. “In defence, he prefers an aggressive pressing approach. In a 4-1-2-1-2 shape which sometimes shifts to a 4-3-1-2 or a 4-3-3, his team position themselves high up the pitch and have an extremely narrow defensive block as they look to force the opposition wide. His possession game is compact and combinative, (looking to) move the ball quickly up the field through fast and dynamic …

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