This past summer transfer window, Tottenham Hotspur watched arguably their biggest ever club legend ride off into the Los Angeles sunset, as Son Heung-min left Spurs with his head held high as the team's leading goal contributor in the Premier League and a Europa League champion, signing on with MLS giants LAFC.
But Tottenham frustratingly never replaced Son on the left wing. They have paid for it dearly, and while watching Son score goal after goal as the second best player in MLS behind only the GOAT Lionel Messi himself, Spurs are left ruing their own left wing situation where their best option is a still entirely too raw Wilson Odobert.
During the summer transfer window, Tottenham were rebuffed with their original interest in dream left wing targets Rodrygo Goes and Savinho. And then when they did have the chance to go after a quality, available option in Ademola Lookman, who was openly upset with Atalanta's treatment of him, Spurs frustratingly did not pull the trigger on a deal.
Tottenham aren't the only ones interested
Lookman is still in Bergamo and still playing pretty well despite his gripes with the club, and he is still available for Tottenham to sign. And according to a report from Tutto Juve's Massimo Pavan in Italy, Tottenham have seen Lookman's continued issues with Atalanta and are actually stepping up their interest in the Nigerian forward further ahead of the January transfer window.
They aren't the only ones involved in the sweepstakes, as Spanish giants Atletico Madrid have also reportedly increased their interest in the 28-year-old, who has been one of the best players in Serie A over the last few years and was a legitimate Player of the Season candidate in 2024/25.
Lookman could cost 60 million euros, per Tutto Juve, though, interestingly enough, Spurs and other clubs were quoted a lower fee than that last summer. If Spurs can sign Lookman for under 50 million euros and whittle down the asking price with Atalanta surely desperate to get rid of a player who clearly wants out, he could be the best deal possible on the left wing, especially if Spurs want to sign someone right here, right now so that Mathys Tel and Odobert aren't under so much unfair pressure.
Tottenham honestly should have made a play for Lookman last summer, in hindsight, and made sure they had at least someone with a reasonable track record to semi replace Son Heung-min. Better late than never.