Barry Windham is easily one of my favorite wrestlers. Top five, even.
Coming into this tournament, I was hoping to see Windham among the entrants. I didn't expect he would go really far in this tournament but hoped he'd at least get a decent showing. So of course I was happy when seeing his first round match was an easy one. This isn't even close.
Raven was a great personality and was pretty relevant for about five years. He was a big deal in ECW and a medium sized deal in WCW. His WWF run was mostly notable for winning a bunch of hardcore championships, which means it wasn't really notable at all. Windham was a big deal in Florida(in which the talent level is easily the equal of ECW's), and a big deal in the NWA/WCW. He had a couple shitty WWF stints but also managed to win their World tag title twice.
Raven was a pretty good wrestler and remembered for running with his Flock. They were a pretty entertaining and interesting group. Windham was running with the Four Horsemen, probably the most iconic stable in wrestling history. People who weren't watching wrestling then may not realize, but as a babyface, Windham was extremely popular. After his turn, he was always among the top heels in WCW. Raven had a really cool, dark persona and it was probably his best characteristic. Windham was no slouch in charisma, and got big reactions for a decade. He was the guy the NWA felt comfortable allying with the top faces to go after the Horsemen and that WCW felt comfortable putting into their most important product, the Horsemen.
When I think of Raven, what really stands out are his feuds. He had a few classics in ECW; his stuff with Dreamer is legendary. Good as they were, they don't stack up with Windham going sixty minutes with Flair, or his feuds with the Horsemen or Dusty Rhodes or Lex Luger.
In-ring wise, Raven was fair. His talent was in his character and storytelling. Windham was an exceptional performer, very solid technically and with good size. Their wrestling skills aren't even close. Huge advantage Windham.
When comparing accomplishments, Windham is far superior. Raven's top prizes were a couple good ECW Heavyweight championship runs. He, like Windham, won a NWA World title. But the NWA was far more relevant when Windham was the champ than during Raven's reign. Windham won the US title and had a dominant run when it was still a very prestigious belt. Raven won it, too, when it didn't mean as much-and kept it for a day. Windham also won numerous titles in Florida, which was a very strong territory, a TV title and held the Western States strap.
Raven had a lot of success as a tag wrestler, winning the ECW belts on a handful of occasions and even the WCW World titles. Even here, his resume pales to Windham's; Windham was a two-time WWF World Tag champion with Mike Rotunda, who he also won several Florida US tag titles with. He was an NWA World Tag titleholder with Tully Blanchard. He teamed with Ronnie Garvin to win a NWA US Tag title, teamed with his brother, Kendall to win a WCW World Tag title and then with Curt Hennig to win another. He's one of the more accomplished tag team competitors in history.
Windham was much more technically sound, was a lot bigger, was quicker, and had more stamina. There weren't any ring skills he didn't have an advantage over Raven in. He held more titles, was a part of bigger storylines, spent more time at the top of the card and was over with fans for more than a decade.
Raven was twisted and might try some of his psychological games, but it wouldn't affect Windham. Barry was a pro's pro who came from a wrestling family; he wouldn't get psyched out by Raven. After getting in the ring, Windham would be too good for Raven. Raven might get some short, occasional offense, but Windham picks him apart. The Flock may try some shit, but Tully and Arn(along with JJ's shoe) are more than a match for Raven's lackies. Windham superplexes Raven and makes him cry uncle to the claw, picking up the win in under ten minutes.