Good luck to him - Spurs lad through and through, and deserves a decent sendoff.
In the end, his career from here on in depends on if he can avoid being the disappointment that he was for most of his time here, and that in turn depends on if his future teams can play him in a role that suits him instead of jamming him into defensive midfield as we did.
His early promise as a central midfielder blinded everyone about *why* he was successful in that role to begin with. He was never particularly quick, strong or physically dominant - like with most of our midfield production line, from Tom Carroll to Alex Pritchard to him to Skippy, he was a tidy, technically competent midfielder with an edge. But in the PL, you need dominant midfielders to survive - or you either need a) midfielders of unparalleled football intelligence to overcome their physical limitations, like Modric, or b) a system that minimises the physical demands on central midfielders to be all aspect enforcers, pressers dribblers, etc.
Under Poch, we played the latter. We pressed really high up, so our first defensive line was Kane, Son, Dele and Eriksen, and if the ball got past them into midfield, Verts or Toby would step up to challenge high. At worst, Sissoko would clean up the mess.
In this role, Winks' qualities as a technical distributor were sufficient to keep him in the side despite his limitations. But when we stopped pressing, when we dropped deep, when we needed him to be a more 'classic' central midfielder screening the back line alongside Hojbjerg and winning the ball back to spring counters, he failed miserably as all his physical limitations were exposed - slow, weak, hesitant.
Somewhere in there is a great Jorginho-style midfield metronome, or a surprisingly good 10. Just, don't ask him to do anything physically demanding in midfield.
Adios, Winksy. Thanks for the memories.
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