There is no position Tottenham Hotspur needs to upgrade more this winter transfer window than the left wing position, because it's been a huge void in the absence of legend Son Heung-min, who left for MLS in order to avoid a stronger decline in the Premier League, leaving on a high note.
Spurs have simply failed to replace his production at the position, and though they do have two very good young players in that spot between Wilson Odobert and Mathys Tel, it's unfair for Spurs to ask them to carry that torch - at least not immediately.
But as the January transfer window approaches, there are less obvious upgrades that Spurs fans are talking about upgrading, and one of the more out of nowhere ones would be a new goalkeeper to supplant Guglielmo Vicario.
Tottenham may want an elite option
Although Vicario is a great goalkeeper and one of the best in the Premier League, some Spurs fans feel that he has a ceiling because of some of the basic positioning errors he makes that lead to back breaking goals. They are not overshadowed by the great plays he makes, but they do stick out in comparison to goalkeepers like David Raya, Alisson Becker, and Gianluigi Donnarumma at the main title contenders in England.
Per a recent report from the Daily Mail's Matt Barlow, Tottenham Hotspur could be looking for a new world-class goalkeeper this January to upgrade on Guglielmo Vicario. Barlow writes that while a new striker is the priority for Spurs this winter, Tottenham feel that because Vicario is so poor on set pieces and does not command his area like an Alisson or a Donnarumma, they are interested in finding someone else.
Well, honestly, good luck doing that in January. It is so, so hard to find a great goalkeeper signing in this month, and the only real time that's happened is with a veteran keeper on an expiring contract signed in a pinch for a small fee. That goalkeeper was Yann Sommer, who joined Bayern Munich for six months to help them win the league after Manuel Neuer's skiing accident.
Tottenham aren't going to find that kind of an opportunity this winter, unless if James Trafford really does push his way out of Manchester City to step out of the shadow of Donnarumma after a frustrating summer 2025 transfer. That's the player to watch, though, between Vicario and Antonin Kinsky, goalkeeper isn't yet a priority target for Spurs.