Tottenham were dealt a blow this week when highly-rated defender Luis Binks opted to move to the MLS.
In a bizarre twist of fate, the 18-year-old will link-up with ex-Arsenal star Thierry Henry at Montreal Impact.
The Daily Mail claims that Jose Mourinho tried to talk Binks out of the move.
It is thought that the Tottenham man had become frustrated with what he believed to be a lack of a pathway to the first-team.
Despite not making a first-team performance, Spurs could live to regret not doing more to keep Binks.
The centre-back was held in high regard by the academy staff at Tottenham.
He’d played eight times for the club’s under-23 outfit this season and looked largely impressive.
A pathway might have been in place for Binks had he stayed.
Mourinho has utilised Japhet Tanganga in recent weeks, whilst Oliver Skipp came on as a substitute in the midweek FA Cup win.
Troy Parrott is also likely to sign a new deal, although the boss has suggested he isn’t quite ready for the senior ranks just yet.
His departure is perhaps all the more surprising given a lack of centre-backs at Tottenham.
Toby Alderweireld is very much the top man but after that, there is very little.
Davinson Sanchez is young and could still improve and Jan Vertonghen will probably leave when his contract expires in the summer.
Eric Dier can play centre-back but has been out of form and Juan Foyth seems well out of the picture.
With Tottenham still fighting on three fronts this season, Mourinho could have utilised Binks.
If he wanted him to stay, he clearly valued him but he needed to prove it to the player.
In the FA Cup, the boss has chosen to put a mixture of youth and experience in his team selections.
Throwing the centre-back onto the bench might have at least convinced Binks to stay a bit longer.
Only time will tell whether Spurs truly regret letting Binks leave.
Allowing him to walk away so easily, however, will sting. If he goes onto do great things in football, Tottenham and Mourinho might be left looking very foolish.