After the end of a two-year search for identity that began with a $218 million summer transfer window in 2017 and concluded with the sacking of club legend Gennaro Gattuso as manager at the conclusion of this season, Milan settled on fun. A proactive managerial search featured a musical chair of Italian managers ranging from Antonio Conte to Eusebio di Francesco to Maurizio Sarri, but Milan hired a relative unknown in Sampdoria’s Marco Giampaolo. Giampaolo represents the club’s sixth manager since Max Allegri left in 2014, each tasked with the challenge of re-establishing their place within the European football royalty. Giampaolo took a decidedly lighthearted approach when laying out his ambitions during his introductory press conference, saying “my dream is to train while having fun - when the playful aspect disappears, then there are problems.”

That looseness and sense of improvisation is a foundation to his unique approach that gained supporters despite an 11^th, 10^th, and 9^th place finish in his three years at Sampdoria. No doubt Giampaolo was helped by viral clips on social media showcasing his midtable side moving the ball quickly up the field with one-touch passes and off-ball movement. Formations are neutral, but Giampaolo is tethered to his 4-3-1-2 shape with a diamond midfield rarely scene in the contemporary game – at least outside of Italy. In this pressing era, his style features perhaps the most anachronistic position of the modern game in a playmaking #10. Though the natural shape of having two strikers backed by an attacking midfielder also gives provides an easy man-marking system without the ball if an opponent spreads their two centerbacks wide and drops a midfielder back. 

We caught glimpses of Sampdoria’s play with Fabio Quagliarella’s goals seemingly going viral every month on his way to leading Serie A with 26 goals in 37 matches. Giampaolo brings a possession-based philosophy, but with small nuances: one quirk of his buildup play is how deep the fullbacks remain during the initial buildup phase as opposed to providing width by pushing high up the field. This places the emphasis in the center of the field among their three center midfielders, though their key is finding their playmaker with the ball in between the lines with two strikers making runs in front of him. The compactness of the four midfield players promotes quick passes and third-player runs. One touch passing and movement is how his sides create and exploit space. 

There is footage from 2016 of Giampaolo’s Empoli side dictating play against Max Allegri’s Juventus, though many will point to Juventus’ 1-0 win as the most important detail in that match. Regardless, Giampaolo is part of a group of possession-based Serie A managers alongside the Maurizio Sarri, Gian Piero Gasperini, and Roberto De Zerbi adding nuance to a cautious, defensive brand. Their fundamental approach is baiting opponents to press, then breaking that press with one-touch passes and quick movement. Perhaps most important to Milan, player development goes hand-in-hand with Giampaolo’s approach. Torreira, Fernandes, Patrik Schick, and Milan Skriniar are among those who made moved to bigger clubs after spending time with Giampaolo’s Sampdoria. With a new budget at Milan, he may be able to see out the full development of his prospects who left in their early-20’s (Torreira is rumored for a loan move to Milan). 

One could easily associate Giampaolo’s innovative approach to possession with youthful exuberance, yet Giampaolo is 51 years old. His rise at a later age mimics other attack minded Italian managers like Sarri, who got his first big job with Napoli at age 55 and Gasperini, who managed Inter at age 52. Giampaolo was molded by his long journey to eventual prominence: he began his managerial career in 2004 at Ascoli, and has managed the following sides in both Serie A and Serie B in the last 15 years: Cagliari, Siena, Catania, Cesena, Brescia, Cremonese, Empoli, and Sampdoria. The three years he spent at Sampdoria was the longest he stayed with any one side. The late-bloomers bring to mind the idea of two contrasting modes of genius, one of conceptual innovation and another developed through trial and error over time. Giampaolo, at his introduction, said that he has “remained faithful to the principle that one never stops learning and working with continuity is increasingly enriching the wealth of knowledge.” 

Possession and positioning are Giampaolo’s paintbrush and canvas. A deep lying midfielder dropping back a few feet, center backs spreading wide, strikers pushing up to create space in between the lines for a playmaker – these are the small tweaks that uphold the larger idea of creating space and unlocking opponents. It may be obvious to say that a manager is better at age 51 than at 41, although there are as many examples of managers failing to update their style after their initial spark. Yet Giampaolo’s career, like Sarri and Gasperini, has crescendoed with age. With the talent on their squad, Milan may find immediate success with a tactical system honed over a decade. 

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Milan finished one point behind Inter and Atalanta last season for the final Champions League’s spot, a competition they have not played in since 2014. Although not that making the tournament would have mattered much this season as the club recently withdrew from the Europa League due to a Financial Fair Play ruling. 

Milan first went for nostalgia in appointing former players Clarence Seedorf and Filippo Inzaghi as managers to recapture that feeling. When that failed, they went straight to spending, putting them in their current predicament. Under CEO Ivan Gazidis, who cut his teeth at Arsenal for over a decade and arrived in Milan in 2018, there is a newfound approach to squad-building focused on a long-term approach. Gazidis laid out his goal to modernize Milan through player development as opposed to high-priced signings, already refusing to sign Cesc Fabregas and Zlatan Ibrahimovic. The best executives have their story in how contemporary decision-making plays into the larger story of the club.Gazidis aims to cut through the “illusions and lies” of Milan’s recent financial boom and bust, adding that “the story of unfulfilled beautiful promises is over.”

Giampaolo is tasked with the responsibility of uncovering Milan’s truth, then. The usual question when a manager moves from mid-table to a top club is whether their pragmatic style would be enough to get results with larger expectations. Yet Giampaolo’s attacking instinct should only be augmented by Milan’s budget as compared to Sampdoria. Playmaker Gaston Ramirez can turn into the $40 million Lucas Paqueta, the 36-year-old Quagliarella into the 23-year-old Krzysztof Piatek. When nostalgia and big-spending fail, it’s back to the basics of small experiments and incremental iterations honed over 15 years, that may add up to a masterpiece one day.