The No. 1 priority for Tottenham Hotspur this January transfer window is to add attacking talent to a squad that appears to be doomed to a finish in the bottom half of the Premier League table. Spurs do not have an established goal scoring option, and now with Mohammed Kudus injured, they arguably have desperate needs on both wings - not just the left hand side.
Spurs also have needs in midfield and at left back, and if you ask many of the Tottenham faithful, they will also convincingly argue that a more stable goalkeeper to replace Guglielmo Vicario would also be ideal in 2026.
Vicario is a perfectly fine shot stopper, but his lack of leadership skills and horrible handling and on the ball ability have made him an enemy to many Spurs supporters. He is not someone the club feel safe with in goal, and if a better target were to emerge, perhaps Spurs would consider making a move.
Tottenham might not get the best GK target around
The problem is that there are not a whole lot of strong targets readily available. And the most well placed and easieset to sign may soon be coming off the board as a possible transfer target in the 2026 windows.
AC Milan goalkeeper Mike Maignan has been pursued hard by clubs as prestigious as Chelsea, and many Tottenham fans are dreaming of him as an option. The French goalkeeper is on an expiring contract and could technically leave for free now on a pre arranged transfer for the summer 2026 window.
However, Fabrizio Romano is now reporting that Milan are "optimistic to keep" the veteran goalkeeper and are still "pushing" to re-sign him to a new contract ahead of the summer 2026 transfer market. Milan have reportedly submitted Maignan a new contract proposal, and while they are still waiting for official word from the former Serie A and Ligue 1 winning goalkeeper, it looks like they tentatively think he will stay.
All the indications from Max Allegri and AC Milan have been positive that they will get to keep Mike Maignan, and while nothing is set in stone, there are more credible links to Maignan staying in Milano than there are of him heading over to North London to replace Vicario, who has really only been even loosely linked to Italian giants Inter Milan.
Maignan over Vicario is an upgrade in every sense of the word, but, as of right now, there are too many hoops to jump through before Spurs fans can credibly think that this "swap" would happen.