[X] Kalyan 'Canyon' Evans vs. 'The Persian Punisher' Xerxes Attar from SKYLINE. It's rare, but it's great; these two swapped submissions and chained them together like nothing you've ever seen. (Gain trait 'Submission Enthusiast', 1d50XP for Cocky Gimmicks)
I'd go for the Daybreak Match if it it weren't for the Weird Gimmicks Trait, since I really don't want to end up with some Goldust like gimmick. I think the Cocky Gimmick would go really well with the Academy, since Horizon is all about the promos. Tommy could easily become a great heel of he's the cocky average sized rookie, with 'boring' submission matches, who shows up and demands respect from veterans and hostile crowds alike, all while disrespecting them.
In my mind, I'm thinking of Kurt Angle, when he stopped a match to tell the crowd not to boo an Olympic Gold medallist.