AC Milan‘s 2024-25 squad could easily be mistaken for a Chelsea reunion tour. With a number of former Blues players now gracing the pitch at San Siro, it’s almost like Milan’s scouting team had their eyes set on Stamford Bridge’s discard pile.
From Ruben Loftus-Cheek to Christian Pulisic and even Alvaro Morata, the roster is brimming with ex-Chelsea talent. But is Milan turning into Chelsea FC’s satellite club, or is it just a coincidence?
Let’s explore this Chelsea-Milan connection and take a look at how many former Blues have made their way to Italy this season, along with some past transfers, managers, and other links that tie these two iconic clubs together.
Discussion around this started in a recent AC Milan match when fans on social media had a field day with former Chelsea stars Tammy Abraham, Ruben Loftus-Cheek, Alvaro Morata, and Christian Pulisic in a Milan game. The highlight came when Abraham replaced Morata, and Loftus-Cheek came on for Pulisic (all ex-Chelsea players), leading to a flood of posts jokingly dubbing Milan “AC London.”
The connections between the two clubs were hard to ignore, and fans couldn’t resist having a bit of fun with the growing number of ex-Chelsea players now calling San Siro home. The moment sparked plenty of banter online, with fans playfully celebrating this quirky “Chelsea takeover” of Milan.
Currently, there are 5 ex-Chelsea players in the AC Milan team.
The most recent player to be part of this connection is 27-year-old English striker Tammy Abraham, who has joined the Rossoneri from AS Roma on loan for the 2024-25 season. He joins the likes of midfielder Ruben Loftus-Cheek and the American winger Christian Pulisic. Loftus-Cheek joined Milan in July 2023 for a fee of €18.50m from the London-based club.
This was after 19 years at Stamford Bridge, where he spent the entirety of his football career. The US National Team talisman Christian Pulisic also followed his mate’s footsteps as he also joined the Rossoneri the same season for a fee of €20.80m.
Ruben is not the only homegrown Chelsea player in the Milan squad, as he also joined ex-Chelsea youth academy talent Fikayo Tomori. The centre-back had joined San Siro in July 2021 for a fee of €34.40m from the Blues.
Tomori, along with the likes of Spanish striker Alvaro Morata, who also played for Chelsea in the 2017/18 season (after joining from his boyhood club Real Madrid), conclude the current group of ex-Chelsea players that the Rossoneri have.
Historical Transfers and Managers Linking Chelsea and AC Milan
Another player who shared this connection is Thiago Silva, who was most recently the Chelsea captain and leader for multiple years. He joins the illustrious list of men who have won major honors for both these clubs. Silva won the Serie A League with Milan and a UEFA Champions League trophy with Chelsea. Other players, like French national team top scorer Olivier Giroud, have also further worn the shirts of the two clubs in most recent times amongst prolific strikers.
In a different side of the world, however, some players who have not been as iconic as the Brazilian have also shared this connection. The likes of Tiemoue Bakayoko come to mind, especially considering the Frenchman’s disappointing stints at both clubs.
Well, then, as we are diving deeper into this shared link between Milan and London, it would not be fair if we did not mention the very first player to transfer between these two clubs. That man was a gentleman named Jimmy Greaves, who was probably England’s most prolific goal scorer back in the day with over 350 goals. He was part of the only World Cup the nation has won in their history, back in 1966. He moved from Chelsea to Milan for a fee of €80k in July 1961 for the 61/62 season.
Since then, from Ruud Gullit, Marcel Desailly, Michael Essien, Fernando Torres, and George Weah to the likes of Andriy Shevchenko, who had the most high-profile transfer having won everything at Milan and then transferring to London, Chelsea and Milan have seen plenty of star players switch their alliance between the two clubs and share this mutual link.
So, when we eventually combine an XI of this Milan and Chelsea connection, one question comes to mind: who will be the manager? If you’re unsure who’s at the helm of this squad, it’s likely you haven’t been keeping up with European football in recent decades. That’s right—it’s none other than Carlo Ancelotti. The current Real Madrid manager is a two-time Champions League winner from his days at San Siro and the only manager to claim both the Premier League and FA Cup titles in the same season with Chelsea.
As we wrap up our deep dive into the Chelsea-Milan connection, it’s clear that the lines between these two European giants have been thoroughly blurred. With former Blues littering Milan’s current squad, we might as well start calling San Siro “Stamford Bridge South.”
Whether it’s through past players, iconic transfers, or even managerial ties, the relationship between these clubs feels less like a coincidence and more like an ongoing football soap opera. With both clubs sharing a history of high-profile moves, plenty of trophies, and the occasional drama (looking at you, Tiemoue Bakayoko), this isn’t just about transfers—it’s a story of football’s rich, intertwined legacy.
So, will Milan continue to hoard Chelsea’s cast-offs (like in recent times), or is this just the latest chapter in a long-standing football saga? Either way, it’s safe to say this Chelsea-Milan connection is one worth keeping an eye on. Who knows what the next transfer window will bring—maybe the next Milan signing will come with a Chelsea scarf in hand! Until then, we’ll just have to sit back and enjoy the ongoing football love story between London and Milan.
