Re: Winks, injuries in your legs that young can be a destroyer. A couple years with recurring surgery-requiring ankle problems can be devastating. He was highly rated to an extent that exceeded his potential, I think (dined out on a very good performance against Real Madrid for awhile), but was a solid midfielder with the prospects to have a Michael Carrick-esque career.
I think he'll move the needle a decent amount. There wasn't a shred of creativity in Tottenham's midfield last year. None at all. Hojbjerg was their most creative midfielder last year. He'll get double-digit assists just crossing to Kane. That's not to say he's amazing (my words above stand), but he'll do a job for them and gives them something they don't have.