It is arguable that no players to leave Tottenham under Mauricio Pochettino’s watch have been departures that the Argentine has come to regret.
Kyle Walker, who left for Manchester City this summer, is the only candidate that possibly comes close, but the hefty fee Spurs received for the right-back certainly takes away any pain.
But if Pochettino gives the green light for Kevin Wimmer and Vincent Janssen to depart the club, as is being reported, then they are two players that could certainly end up making the Lilywhites boss wish he’d kept them on board.
The Sun believe that Crystal Palace, West Brom and Stoke are keen to sign Wimmer, with the former thought to be winning the race. Meanwhile the Evening Standard suggest that Spurs are happy to let Janssen leave, with West Brom again sniffing around.
Neither player has been given a particularly fair chance of establishing himself in north London, although with the likes of Jan Vertonghen, Toby Alderweireld and Harry Kane in their way respectively that is easy to understand.
But the pair are both young – Wimmer is 24-years-old, while Janssen is a year younger – and could still come good for Tottenham if kept around.
Wimmer, in particular, has shown his ability when called upon; deputising for the injured Vertonghen with aplomb two seasons ago.
Janssen, on the other hand, got in his fair share of scoring positions last season, without being able to finish the chance. It would be a surprise if he repeated his unlucky streak in front of goal again this term.
It is easy to see both players thriving at new clubs and, given the struggles Tottenham have had making signings this summer, the pair's departure may cause Pochettino to question his decision to let them go.