With the mutual termination of Divock Origi’s contract – which was announced on Tuesday – there are no remaining members from the 2022-23 windows.
As La Gazzetta dello Sport writes, none of the players who arrived in either the summer or the winter mercato in the post-Scudetto season are still at the club. Not even those who returned from loans. It is a complete clean-up that hasn’t gone unnoticed, considering only three years have passed.
Charles De Ketelaere
This is undoubtedly the most emblematic case of the gap between expectations and performances. Milan spent the summer three years ago assiduously courting Club Brugge for CDK, ultimately paying €32m plus bonuses. The Rossoneri expected him to be one of the best signings of recent years, a quality player around which to build the rest.
Things went very differently: De Ketelaere made 40 appearances for Milan without a single goal and with just one assist. The result: after just one season, he was loaned out with the option to buy to Atalanta, who subsequently bought him out and where he remains today. This season: 4 goals and 3 assists in 20 appearances (1,444 minutes).
Sergino Dest
Dest arrived at Milanello from Barcelona on the last day of the summer window, in early September. It was a loan with a €20m option to buy: a last-minute move due to Florenzi’s long-term injury, but he never settled by his own admission. The right-back made 14 appearances, with performances completely inadequate to consider the buy-out good value.
Indeed, Milan never considered taking advantage of the deal. “The wrong place at the wrong time,” the player said a few weeks ago. In the summer of 2023, he moved on loan to PSV, who bought him out the following year. This season: 23 appearances (1,895 minutes) with 2 goals and 6 assists.

Divock Origi
With Origi, the circle from 2022 to today closes. He leaves as one of the worst investments in Milan’s modern era. Having arrived from Liverpool on a free transfer, he signed a contract until 2026, making €4m net per year and amassing just 36 appearances (1,187 minutes) with two goals and one assist.
The last trace of him dates back to a Juve-Milan match on 28 May 2023, after which the Belgian disappeared from the radar. Officially included in the Milan Futuro squad, he never showed up, and not even a loan deal to Nottingham Forest helped him rehabilitate.
Malick Thiaw
In recent weeks, with the team starting to concede a two goals per game, there was a lot of chat about whether Thiaw might be useful. Malick left the Rossoneri last summer for Newcastle United, where he is now highly regarded.
He went partly because he was tempted by a move to the Premier League, and partly because €40m was too good to turn down. Current season: 23 appearances (1,940 minutes) and two goals.
Aster Vranckx
The idea – or rather, the hope – was to reach the end of the season with plenty of good reasons to exercise the option to buy Vranckx permanently from Wolfsburg, but that wasn’t the case. The Belgian midfielder found very little playing time with Milan.
He racked up only 10 appearances (318 minutes), with one assist. So he returned to Wolfsburg, who sent him back to Italy this summer (on loan), where he is now at Sassuolo. He had an encouraging start there, then his minutes dwindled, and he also suffered some physical issues.
Devis Vasquez
Vasquez was the only signing in the January 2023 winter transfer window. Signed from Guaraní as a promising goalkeeper, he began a loan spell from which he has virtually never recovered.
First Sheffield Wednesday, then Ascoli, then Empoli. Milan no longer believed in him, and last July his contract was mutually terminated. As a free agent, he joined Roma, where he has yet to make his debut.
The loanees
Even all those who returned to Milanello from various loan spells in 2022 are no longer wearing the Rossoneri. Yacine Adli has emigrated to Saudi Arabia to play for Al-Shabab (a permanent transfer), Marco Brescianini is at Atalanta (a permanent transfer) and Mattia Caldara has retired.
Lorenzo Colombo is at Genoa (on loan with a conditional obligation to buy), Leo Duarte is in Turkey at Başakşehir, Tommaso Pobega is at Bologna (also on loan with a conditional obligation to buy), and Alessandro Plizzari is at Venezia.

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