Tottenham Hotspur have been trying to make significant sales in recent months in order to clear up squad space and raise funds, but they have had to make some tough decisions on that front. This past summer, club legend Son Heung-min and Spurs mutually elected to part ways with a sale to MLS for a bit of money, as Son was ready to ride off into the sunset after winning a historic Europa League title, exiting the club before the decline really set in.
But instead of finding his heir or using the money to build to the future on the left wing, Tottenham did not sign any left wingers. They have two brilliant young French forwards in Mathys Tel and Wilson Odobert, though manager Thomas Frank is frustratingly not making the most of them.
Spurs ultimately hurt themselves on the left wing by not signing an experienced, established star - like, say, Ademola Lookman - to at least partially replace the irreplaceable icon Son, and thus, now, they are very desperate for a left winger in the January transfer market.
Tottenham are thin on both wings now
Likewise, Tottenham have to learn from their mistake of selling Son without a replacement left winger in the summer by not ending up empty handed on the right wing, too. Because while Spurs were even more right to sell Brennan Johnson this winter than they were to sell Son to MLS, the sale of the Europa League hero to Crystal Palace leaves Tottenham dangerously thin on the right wing, too.
In fact, in the short term, Spurs are actually in bigger trouble on the right than they are on the left. Because while they at least have Odobert and Tel out left, Odobert now has to shift to the right hand side for potentially another month, since Mohammed Kudus has now joined Dejan Kulusevski on the injured list with a multi month ailment of his own.
So sitting in the winter transfer window, Tottenham now have a need on the right wing, too, and players like Oscar Bobb and Maghnes Akliouche to potentially fill it. And looking back at the Son mistake, Tottenham can ill afford to repeat it twice on the other side of the formation.
Now, Spurs are having a hard enough time finding a left winger with players like Antoine Semenyo and Omar Marmoush rejecting them, but the danger of not signing two new wingers this winter - in addition to another midfielder - is much greater with Spurs technically closer to the relegation battle than the top four fight.