Tottenham Hotspur will battle Atletico Madrid in a tricky Champions League Round of 16 tie made all the more trickier by the fact that Ademola Lookman will be playing for the other team instead of Spurs.
Towards the end of the summer 2025 transfer window, Lookman was an increasingly available and attractive left wing option for a Spurs side set to wave goodbye to legend Son Heung-min to MLS. Although Spurs did sign young Mathys Tel permanently to take over on the left wing, everyone knew Tel wasn't ready to be Son's successor and that Spurs needed a veteran left winger.
Lookman had a falling out with Atalanta, and he somehow remained with La Dea after deadline day despite everyone knowing that he wanted out. And that all came down to Spurs not even making an effort to sign one of Serie A's best players.
Ademola Lookman should have been a Tottenham Hotspur
Tottenham could have signed him again in the winter with injuries mounting and the same question marks on the left wing, but they watched Atletico Madrid pick up what has already proven to be one of the shrewdest - and biggest bargain - signings of the winter window, whereas Spurs literally did nothing other than get retread Conor Gallagher from Atleti.
Lookman played a pivotal role in Atletico surviving a playoff round upset from Belgian powerhouse Club Brugge, and now he is the clear danger man to Pedro Porro and the Tottenham defense, which is a group that is lesser than the sum of its parts.
Whereas the Nigerian superstar would have been a game-changing signing for Spurs and their best winger with Mohammed Kudus injured, he will be the most in-form forward in the game and the key difference-maker for Atleti in this Champions League Round of 16 tie.
Lookman could very well be the reason why Tottenham are sitting at home at the end of March, unable to pull off another run to a European Final. His ability to take defenders on, score goals, and his underrated creativity are all things that Atletico Madrid were missing before his signing - and they are all things Tottenham clearly miss badly right about now.
With a goal in La Liga and in the Champions League already, Lookman is a decisive factor for Los Rojiblancos, and he is difficult to stop in one-on-ones. Spurs are the clear underdogs heading into the Round of 16, and Lookman makes their underdog status even more clear at this point.