I genuinely feel for Winks.
He's received a fair amount of banter/shit off Spurs fans over the years, myself included. He didn't pick himself and he wasn't dragging his heels refusing to move on. No one at the club wanted to sell him. The fact that he is HG likely kept him here and unfortunately affected his development. He needed game time and he obviously hasn't been good enough to start for us for a number of seasons. He was never going to improve sat on the bench and any performances that he gave from it didn't represent the best version of him due to the lack of form/confidence/playtime.
It looks like he's finally going to move but he'd be daft to go somewhere where he isn't going to be a nailed-on starter week in, week out. So he has the choice of gambling by playing for a team lower down the table in the toughest league in the world where, to date he has failed to impress OR he can try and push for a move to Spain where his style of football is better suited. Slightly slower pace, less physical, more time on the ball, less pressure. A couple of solid seasons in La Liga and who knows what type of player he develops into.