I'm guessing there are multiple factors that will affect his decision, many of which are out of his hands...
1. How good will Labissiere and Humpries by mid-December?
2. How good will Poythress' surgically repaired knee look?
3. How effective will Lee be in his minutes?
3. Is Wynyard a likely NBA prospect for this year, next year, or further down the line?
If Labissiere and Humphries are handling the center spot well and have no limitations, it seems likely Wynyard will redshirt. If it is believed that the Cats still need help down low, he may not redshirt.
If Poythress' knee looks good and he's playing to his ability, Wynyard won't see the floor anyway. If Alex isn't fully back to 100%, Wynyard could provide some size and strength at power forward.
If Lee has taken a step forward, like most expect, he's going to be getting back-up minutes at both post positions, so Wynyard wouldn't be needed.
If Wynyard plans to try to go to the NBA sooner rather than later, he's likely to play. If he plans to wait at least until 2017 draft, he may redshirt.
I'm guessing Wynyard won't be needed this year. Let me put it this way... if UK needs Wynyard to play right away, it will mean that the Cats are having a poor season and some things have not gone well for our post players. Since I expect Poythress and Lee to play like upperclassmen and I expect Labissiere to get the lion's share at center with Humphries provided mop-up duty, I think Wynyard will redshirt.