Weston McKennie has emerged as a surprise target for Milan as the club explores potential midfield reinforcements after the 2026 World Cup. With his contract situation unresolved and his market value rising, speculation is intensifying over a possible move that could reshape both his career and Milan’s midfield structure. In the background, two familiar figures could quietly influence the decision, Christian Pulisic and Massimiliano Allegri, adding a compelling narrative to what could become one of the most intriguing transfer sagas of the upcoming window.
McKennie’s future at Juventus is increasingly uncertain. The American midfielder is entering the final months of his contract and could be available on a free transfer in the summer of 2026, prompting the Rossoneri to begin preliminary discussions with his representatives.
According to Calciomercato, Milan has initiated informal contact to explore the possibility of signing the United States national team midfielder without a transfer fee. Juventus remains keen to retain him, but negotiations over a contract extension have yet to reach a breakthrough.
Weston McKennie of Juventus celebrates after scoring a goal.
He currently earns around $3 million per season, with the Bianconeri prepared to offer a new deal worth $4.7 million annually over three years in an attempt to secure his long-term future in Turin. Despite this, the midfielder’s growing market interest has made the situation increasingly complex.
McKennie’s rise under Luciano Spalletti and Milan’s midfield plans
The American’s resurgence has been one of Juventus’ key storylines this season. Since Luciano Spalletti’s appointment in late October, he has scored seven goals and provided four assists across all competitions, showcasing his versatility and influence in midfield.
His ability to operate in multiple roles, from central midfield to wide positions, has made him one of Juventus’ most valuable assets. This form has attracted interest from across Europe and beyond, especially from Milan, which is assessing several midfield options as it looks to strengthen the squad with experienced players who could arrive without a transfer fee. McKennie has joined Leon Goretzka on the club’s shortlist, as the management evaluates cost-effective opportunities in the market.
The club already boasts a strong midfield core featuring Luka Modric, Adrien Rabiot, Youssouf Fofana, and Samuele Ricci, but the technical staff believes additional depth is required to compete on multiple fronts. Inter and Roma are also tracking McKennie’s contract situation closely, ensuring that Milan will face significant competition if they decide to make a formal approach.
The key factors revealed: Pulisic and Allegri
Calciomercatofurther adds that Massimiliano Allegri’s respect for McKennie and his close friendship with Christian Pulisic could play a crucial role in convincing him to join Milan. Allegri previously managed McKennie at Juventus and is known to value his tactical versatility and work rate.
Meanwhile, Pulisic and McKennie share a long-standing friendship from their time with the United States national team, and the prospect of a USMNT reunion at San Siro could be a powerful personal factor. The Rossoneri are said to be gathering detailed information and will evaluate whether to submit a concrete proposal in the coming weeks.
im Ream #13, Weston McKennie #8, Christian Pulisic #10, and Antonee Robinson #5 of USMNT
If the move materializes, the San Siro side could reunite two key United States national team players in the same club setup, a rare scenario in European soccer. Such a partnership would strengthen the team’s midfield dynamism while offering McKennie a familiar presence in a new environment. From a sporting perspective, his versatility and box-to-box energy would complement Milan’s tactical structure, while his leadership and international experience would add maturity to the squad.
