Milan kicked off their 2025 preseason tour with a closely contested 1-0 loss to Arsenal in Singapore, a match that marked the debut of Massimiliano Allegri’s second stint in charge of the Rossoneri. While the scoreline reflected a tight contest, the fixture offered a deeper glimpse into the new manager’s tactical intentions and hinted at a reshuffling of player roles within a squad in transition.
After a chaotic 2024-25 campaign that saw Milan finish eighth in Serie A and miss out on European soccer, a complete overhaul was inevitable. Discontent among supporters, disappointment over the exits of Paolo Maldini and Ricky Massara, and a string of failed coaching appointments led club owner Gerry Cardinale and new sporting director Igli Tare to make a bold call: bring back Allegri.
Fresh from his last Coppa Italia triumph with Juventus and subsequent dismissal, the 57-year-old boss returns to a club he once led to the Scudetto in 2011. Now tasked with restoring order, his early preseason decisions — from formation changes to positional experiments — have already stirred interest.
In his first outing, he opted for a 3-5-2 system. His backline featured Fikayo Tomori, Malick Thiaw, and Strahinja Pavlovic, while Rafael Leao and Christian Pulisic spearheaded the attacking line. Notably absent were Luka Modric and Santiago Gimenez, still on extended leave after international duty, and goalkeeper Mike Maignan, who was not fully fit.
What the Arsenal friendly revealed about Christian Pulisic
Despite being more of a training exercise than a competitive clash, the match carried important clues. Bukayo Saka’s second-half strike gave Arsenal the win, capitalizing on a momentary lapse in Milan’s defensive concentration. Yet, the Rossoneri’s improved structure under Allegri was evident. They sat deep, held their lines, and limited the Premier League giants to half-chances thanks to composed defending and standout goalkeeping — particularly from Pietro Terracciano and young Lorenzo Torriani, whose series of spectacular saves earned applause.
While headlines focused on the result, many eyes were on Christian Pulisic. Now entering his third season with Milan, the USMNT captain is expected to be a cornerstone of Allegri’s project. The Gunners’ friendly revealed that the American could see his role shift under the new manager.
With no natural striker available — Lorenzo Colombo started but is expected to leave — Pulisic played as a wide forward. Yet, he often dropped deep to support the midfield, helping debutant Samuele Ricci progress the ball and offering transitions between defense and attack. He showed strong fitness levels and sharp ball control, even setting up Alexis Saelemaekers for Milan’s best first-half chance.
Allegri withdrew the American at halftime, likely with an eye on workload management. Still, his role in the first 45 minutes hints that Pulisic could be deployed more centrally or as a hybrid creator, especially when paired with Leao or when Milan lacks a natural centre-forward.
What would Milan expect from Pulisic under Allegri?
This season could prove pivotal for Pulisic, who is also preparing for the 2026 World Cup on home soil. Since arriving from Chelsea in 2023, he’s become a fan favorite at Milan, but Allegri’s arrival presents a new chance to elevate his standing.
The manager’s track record with creative attackers — from Paulo Dybala to Carlos Tevez — suggests Pulisic could thrive if given freedom within a balanced system. And with talks of a contract extension ongoing, there’s a clear intent from both club and player to build something long-term.
