If there's one overarching criticism of Tottenham Hotspur over the years, then it is the fact that Spurs have never been a particularly ambitious club. They rarely, if ever, compete with the other big clubs in European football for signings, they never spend that extra bit of money to push the club forward, and they have always been content with being not even second but fourth best to the rest.
Spurs have been trying to show fans this year that they are turning a new leaf with their fancy stadium, and while they did some nice players this summer in Xavi Simons and Mohammed Kudus, it was all only after finishing a ghastly 17th in the Premier League.
Then, Tottenham finally fired Daniel Levy, and if Spurs want to prove that they have changed as a club and that it was all Levy holding the team in the doldrums at the bottom of the Big Six in terms of ambition, then this January transfer window is a prime opportunity to do just that.
Tottenham are fifth in the Premier League, sitting outside the cusp of the Champions League places, though they are in position to crack those spots despite, analytically, being poor with an expected ranking of 16th in the division.
Tottenham need to make a move now
There are still a few remaining needs left in this squad, but no need is more glaring than the left wing position. Without Son Heung-min, the left wing spot is even worse than expected, and while the young duo of Wilson Odobert and, occasionally, Mathys Tel can be sufficient against the lesser teams, neither young player is ready yet to be "the guy" on the left wing for Tottenham.
If Spurs want to make sure they qualify for the Champions League again next season, then they are going to have to sign a top left winger in the January transfer window. That is simply non negotiable at this point, because Spurs are leaving goals and assists on the table by not having an established player in that position.
Now, Spurs could also benefit from a new striker, but between Dominic Solanke and Randal Kolo Muani, there's enough that Spurs don't have to spend 50 million euros or more on a proven option. But it is absolutely worth it for them to spend that kind of money on an Antoine Semenyo or an Ademola Lookman who can come right in and threaten for double digit goals and double digit assists as a progressor, one on one playmaker, assist provider, and goal threat.
Tottenham need that kind of well rounded help, because a top left winger can take pressure off the strikers to score while also taking pressure off a signing who is working out big, Mohammed Kuuds, on the right wing. Kudus would benefit greatly from the space a top left winger would add to the Tottenham attack.
Spurs signing a top left winger could mean the difference between securing a finish in the top four and one completely missing the European places. Even small teams like Wolves have exposed how little attacking talent Spurs still have, especially relative to the best teams in the Premier League. The left wing position has been a black hole since the decline and departure of Son, and it must be adequately addressed this winter by upper management.