Milan transfer regret as Thiaw’s claims on Allegri resurface

Originally posted on Football Italia | By Lorenzo Bettoni | Last updated Dec 19, 2025 9:50 AM ET

Milan have conceded two goals in each of the last three matches, and Malick Thiaw’s performances with Newcastle have prompted Italian media to suggest that selling the German centre-back in the summer was a mistake, especially because Massimiliano Allegri wanted him to stay.

Thiaw joined Newcastle from Milan in a €42m deal last summer.

The Germany international has quickly become a regular starter at St. James’ Park, playing every minute across all competitions since September 21.

Thiaw had been struggling with consistency during his three-year spell at Milan, so last summer’s big sale was regarded by Italian media as an excellent piece of business for the Rossoneri.

Milan’s defensive issues

RIYADH, SAUDI ARABIA – DECEMBER 18: David Neres of SSC Napoli scores his team’s first goal during the Supercoppa Italiana Semi-Final match between SSC Napoli and AC Milan at King Saud University Stadium on December 18, 2025 in Riyadh, Saudi Arabia. (Photo by Yasser Bakhsh/Getty Images)

Recent matches, however, have shown the defensive fragility of the Diavoli, who haven’t yet kept a clean sheet in December, conceding two goals in each of the last three matches.

Milan replaced Thiaw with Koni De Winter last summer, but the former Genoa defender has failed to match expectations and was particularly criticised after Napoli’s 2-0 win in the Supercoppa Italiana semifinal on Thursday.

De Winter is not a starter at San Siro, but last night he replaced the injured Matteo Gabbia.

Why Thiaw joined Newcastle from Milan

As Calciomercato.com and TMW note, Milan’s decision to sell Thiaw might bring even further regret when considering that Allegri was eager to give the German regular playing time this season, as the Newcastle defender said in November: ” I had three good years at Milan, but at the end I didn’t really play that much. Allegri told me that I would’ve had a chance this season, but I wanted to try something different.”

Following eliminations from the Coppa Italia and the Supercoppa Italiana, Milan only have Serie A left to play for this season, not being involved in any European competition.

This article first appeared on Football Italia and was syndicated with permission.

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