Speculation (Winston will probably leave)

I don't know about all your conclusions but the injury report thing was significant. There are consequences if you try manipulating those. If Winston truly believes he's not healthy then it could become a big issue with the organization. I hope they wouldn't do something that dumb.
Damned if they do and damned if they don't.
But at this point they might as well let him play. It's not like we're going anywhere.
But if he goes out and gets hurt everyone will be screaming to the moon about what a horrible decision it was to play him when he wasn't healthy.