It is no secret the serious bad blood Vince had for Barry Windham for leaving the WWF at the end of 85 right in the middle of the feud with the Dream Team and then again in 89 as Barry stated in his shoot interview Vince never forgave him for bolting in 1985.
How did Barry end up back there in 96 as The Stalker?
He had last been seen in WCW for a one shot comeback as the mystery man Col. Parker brought in to face Ric Flair at Slamboree 94 then quietly disappeared again right after.
Was WCW in the mix to bring him back in 96 or was Barry pretty much eyeing the WWF for his comeback?
He seemed unmotivated and miserable during his WWF return and got very out of shape during the run.
Was Vince giving Windham the Stalker gimmick punishment for leaving so much or did Windham just not care enough to get it over?
Oh, Windham clearly didn’t give a crap at that point and just wanted an easy payday. Can’t blame him, given that the character was introduced as a heel and then randomly starting working as a babyface on TV, plus they couldn’t even decide whether to call him “Stalker” or “Barry Windham” when calling the matches. I know Vince pretty openly held a grudge, but he was so desperate for warm bodies to fill up the shows at that point that I’m sure he just wanted to bring in Windham to make sure WCW didn’t get him. From following the Observers at the time, though, I can tell you that there was no bidding war, it was just one day “Oh, Barry Windham will be coming in as the Stalker”. But previously he had been talked about as early as Royal Rumble as coming in as a partner for Goldust (which led to the wacky “Silverdust” jokes from Dave) so clearly the interest was there from the WWF for whatever reason.