Christian Pulisic has become the reference point of Milan’s attack, a player around whom identity and ambition are slowly being rebuilt. With Massimiliano Allegri on the bench and January looming, the Rossoneri are once again scanning the market for reliability, versatility, and experience. Amid concerns about depth and balance, a familiar profile has quietly resurfaced—one that could strengthen Milan immediately while also serving a very different long-term objective: staying visible ahead of the 2026 World Cup.
The Italian Super Cup semi-finals defeat to Napoli did more than end a trophy run—it exposed structural problems. According to MilanNews, the players returned from Riyadh with more doubts than answers, particularly surrounding a summer investment that has yet to justify itself.
Three of the club’s most expensive recent signings—Koni De Winter, Ardon Jashari, and Christopher Nkunku—were all part of a starting lineup that struggled badly against Napoli. Nearly $105 million worth of talent failed to deliver in a defining match, a statistic that has sharpened scrutiny around squad construction.
Allegri, however, was careful in public. After the defeat, he refused to be drawn into transfer talk: “Talking about the transfer market now is pointless. We need to focus on working hard and rebuilding a solid defense.” Behind the scenes, though, the picture is clearer. Milan needs reinforcements—not just in defence, but in midfield, where balance, intensity, and tactical flexibility have been missing.
This is where an old Allegri favorite re-enters the conversation. A midfielder who knows Serie A inside out. A player Allegri trusted for years. And someone whose club situation has quietly drifted toward uncertainty – Weston McKennie.
Contract stalemate opens the door amid World Cup pressure
At Juventus, McKennie’s situation has stalled dramatically. According to SportItalia journalist Alfredo Pedulla, contract negotiations have gone quiet, with “no advanced talks regarding a renewal.” The midfielder’s deal expires soon, and Juventus’ priorities lie elsewhere—most notably in securing Kenan Yildiz’s future. With resources focused on younger cornerstones, McKennie has slipped down the list despite remaining useful across multiple systems.
This is not a reflection of decline. In fact, the American has continued to show remarkable tactical versatility, playing as a central midfielder, wide midfielder, and even further forward under different managers. But versatility without security creates a dangerous limbo—especially in a World Cup cycle.
Weston McKennie #8 of the United States is congratulated by Christian Pulisic #10 after scoring a goal.
For the 27-year-old, the stakes are clear. With the 2026 World Cup approaching on home soil, regular minutes are non-negotiable. Remaining at Juventus without clarity risks stagnation. A move—whether permanent or short-term—becomes a strategic necessity rather than a gamble.
Several Premier League clubs have been monitoring the situation, but Serie A offers continuity. Milan, in particular, offers something more: familiarity, tactical trust, and a teammate who understands the same international pressure. That teammate is Christian Pulisic.
Pulisic, Allegri, and a natural fit
The potential appeal of Milan is not accidental. Allegri knows McKennie well from their Juventus years together. And Pulisic has already spoken positively about the Italian coach’s personality and methods: “I spoke with Weston recently, and he only had positive things to say. He told me Allegri is a fun guy, loves to joke around, very passionate… I think he’s the right choice.”
Weston McKennie of Juventus interacts with Massimiliano Allegri
On the pitch, the fit also makes sense. Milan’s midfield has lacked energy, transitional bite, and adaptability—three areas where McKennie excels. His ability to press, arrive late in the box, and cover multiple zones aligns neatly with Allegri’s pragmatic approach.
