Coming into the January transfer window, Tottenham Hotspur were already desperate for a new winger who could start on the left side and fill the shoes of Son Heung-min with goal scoring and more experience than the talented young duo of Mathys Tel and Wilson Odobert.
All Spurs have done on the wings so far in the winter window, though, is make a new loan move and a sale. They switched Manor Solomon's loan from Villarreal to Fiorentina, which was smart - doubly so, because with Spurs executive Fabio Paratici moving to Florence, the chances of selling Solomon off permanently increased.
The bigger move, of course, was the permanent departure of right winger Brennan Johnson to Crystal Palace. While that was a wise move, now that star man Mohammed Kudus has suffered a multi month injury with Dejan Kulusevski already out on the right wing for several months with no time table for a return, Spurs have a bigger need for a right winger than a left winger.
Tottenham have no RWs left now
That is because they have no right wingers left, whereas they at least have Tel and Odobert on the left. In fact, Spurs, in their most recent matchup against Aston Villa in the FA Cup, actually had to shift Odobert over to the right, where he did a passable job while Tel quietly shined again.
Tottenham have been running out of winger options anyway, too. Antoine Semenyo was Plan A, but he rejected Spurs to join Manchester City. Spurs then thought Man City would be more willing to sell Savinho after the Semenyo acquisition, but now Savinho is off the table because he is also injured for multiple months.
Plan C was Omar Marmoush, but he has no interest in leaving Manchester City himself. So now Spurs are down to Plan D over in Manchester, and that is 22 year old winger Oscar Bobb, who, like Savinho, is actually more of a right winger than a left winger.
Unlike the others, Manchester City are pretty open about wanting to sell Bobb this winter, but there is a better option on that right wing for Tottenham Hotspur to sign than Bobb. And it all goes back to an old transfer target of Spurs - someone they were already watching closely in the summer 2025 transfer window who they have been watching throughout the season.
Young Monaco right winger Maghnes Akliouche still remains without a transfer and has been quiet on the market, but he was shining against Tottenham brightly in the Champions League this season. Akliouche is a more dynamic and productive player than Bobb, as the Ligue 1 star has three goals and two assists for the Monegasque club this season compared to zero Premier League goals and one assist for Bobb in 2025/26.
Akliouche is only a year older at 23 and is more dynamic. With Kulu's long term value unclear after such a severe injury, Akliouche could be both a Johnson and Kulu replacement, as well as a short term Kudus replacement who can then be a dream backup to the Ghanaian star.