​In football, seasons, momentum, and runs of form evolve at a brisk tempo. The modern game unfolds with such unyielding speed that circumstances can shift in an instant, driven by a multitude of factors both on and off the pitch. Yet four years after AC Milan lifted the 2022 Scudetto, the midfield trio that was instrumental in delivering the club’s 19th Serie A title still looms large in headlines, with their futures continuing to spark widespread discussion across newspapers, outlets, and social media. Sandro Tonali has completed a high-profile transfer to Tottenham, Franck Kessié has entered free agency following the end of his contract with Al-Ahli Saudi FC, where he had played since August 2023, and Ismaël Bennacer has wrapped up his loan spell at Dinamo Zagreb as his next chapter begins to take shape. Of the three midfielders who played pivotal roles during AC Milan’s 2021/22 title-winning campaign, only Kessié appeared at the FIFA World Cup. The Côte d’Ivoire international started all four matches, contributing to wins over Ecuador and Curaçao as well as defeats to Germany and Norway. Back home, anticipation remains about whether the midfielder will continue his international career with Côte d’Ivoire, a development that adds further buzz to the figure known during his time at Milanello as “the President,” alongside the substantial transfer chatter that surrounds him.
Tonali, meanwhile, is poised to work under Roberto De Zerbi at Tottenham. During his time with AC Milan, the Italy international faced Spurs in the 2022/23 UEFA Champions League Round of 16. De Zerbi also has a Rossoneri link, having joined AC Milan’s Youth Sector as a 16-year-old in 1995. Bennacer, for his part, has recently forged a connection with Fali Ramadani’s Lian Sports Group as he begins the next phase of his career. As the transfer window continues to churn, supporters reflect on how this trio’s Milanese success has shaped their trajectories and what lies ahead for each of them in the days to come. The narrative threads—Tonali’s adaptation to a new league, Kessié’s ongoing international considerations and looming decision, Bennacer’s evolving representation and future opportunities—remain intertwined with the broader story of Milan’s past triumph and its ongoing influence on the club’s identity and ambitions.