Daniel Bryan vs Bret Hart in a standard ECW rules match.
This match, if it could ever happen in real life, would be fucking amazing. 20-30 minutes. Submissions applied. Moves countered. False finishes. The crowd would be on their feet from beginning to end for what could be the greatest underdog upset in the history of the business. But who wins?
Bret Hart has the greater legacy. Bret Hart is the obvious choice. Bret Hart is the guy who helped revolutionized the industry and carried the company on his back post-Hogan and Savage. Bret Hart is the best there was, is, and ever will be. It would be a travesty to see somebody the caliber of Bret "the Hitman" Hart, a former tournament winner, eliminated in the very first round of such a legendary and prestigious contest!
But you know what? Upsets happen. BIG upsets happen in pro wrestling because they are fun, unexpected and give huge pushes to guys who need them. Daniel Bryan has all the skills to stand toe-to-toe with Bret. He has all the moves, submissions, counters and a wicked finisher. The men are parallel on so many levels, but Bret has one thing that I believe would actually be a hindrance in this match: honor. Daniel Bryan would go to places I don't think Hart would just to pick up a victory - he'd spit in his face, kick him in the groin, pull the tights or throw his girlfriend in harms way to pull out the win. Daniel could play the straight-up heel in this match, with the fans all behind their Canadian hero, and do a damn good job too! Bryan's victory would be a dirty one, and it would end with the entire crowd booing and throwing trash at him, I guarantee it. This, in a kayfabe tournament, would be the win Daniel could pick up to launch his career and character to the very top.
Add to that the ECW rules stipulation. Bret Hart did make Steve Austin pass out in a pool of his own blood. He's a legit badass. Check. But Daniel is also quicker and willing to do some high risk maneuvers Hart couldn't, and wouldn't (and shouldn't). With so much on the line, I just think Daniel Bryan has more of a chance of being booked in a situation where he'd do everything it takes to beat Bret Hart, even if it means rolling him up with the tights, grabbing a rope or beating him in the face with a steel chair until he's covered in blood. The Hitman would never go down easy, but I do believe eventually....he would go down. And when he does, and realizes Bryan cheated to beat him, there would be an epic rematch unrelated to the tournament in which Bret could regain his honor with a clean Sharpshooter victory.
Maybe it's a huge stretch, but I'm voting for Daniel Bryan for the huge upset victory. The funny thing is, I'm not even that big of a DBD fan.