Tim Sherwood has questioned Tottenham Hotspur's decision to sell Marcus Edwards and believes the decision could come back to haunt the club.
Spurs announced on Monday that the 20-year-old Englishman had joined Portuguese outfit Vitória on a permanent basis.
Edwards had been dubbed as the next 'breakthrough' star during his time at north London for some time.
Over recent years there has been a huge surge in young English talent plying their trade abroad.
Jadon Sancho is the biggest success story to date, having left Manchester City in a cut-price deal to join Borussia Dortmund.
The 19-year-old is now a senior England international and is being touted by the biggest powerhouses in Europe.
Sherwood, who spent a long period of time working with Tottenham's academy before becoming the first-team manager in 2013, is concerned that Spurs may have made a similar mistake with Edwards.
"Yes (he was surprised) because of the talent the boy is," Sherwood told The Debate.
"He'll play in a way that probably doesn't suit Tottenham at the moment. He's an acquired tastemark. He's not a big boy.
"He's a little boy. Very technically gifted. He can play in a telephone box and you'll never get the ball off him.
"If he was at Man City now, he could play in their tight spaces. You know when people sit back against them. That's what's he's like. Now, he's going to a team that's struggling in Portugal.
"Fair play to Marcus, he's decided to take that jump. But will he be able to express himself? If he does then he will move up the ladder and you will see him at a very big club because he has that ability.
"Do I back him to come back and play for a really top club? I really do. I have that belief in him and he needs to keep believing.
"But he needs to find a home. He's probably made the right decision - it's also a wake-up call for the teams. Will they be as quick to let these players go?
"Because they know they could go to the German's, France or Portugal and they could come back and haunt them. So, you have got to make absolutely sure that this kid is not going to make it and come back and haunt you.