Owen Hart didn't really seem to fit in the WWF in 1999. If he hadn't died and remained in the WWF he could have done some great stuff in 2000. In late 1999/early 2000 a lot of guys joined the WWF who would have worked great with Owen. Imagine Owen Hart vs. Chris Jericho, Kurt Angle, Chris Benoit, Eddie Guerrero, and Dean Malenko. Those would have been some great matches.
I'm not sure how long Owen would have stuck around. He had the reputation of being very tight with his money so he could retire early. He didn't participate in the night life that a lot of wrestlers did. He pretty much went to the hotel, called his wife, and turned in early. I think he would have given us some great matches in 2000 and retired sometime in 2001 during the confusion of the invasion angle.
I concur, Owen was years ahead of his time as far as his style would go with WWE and the talent they had later on, he did wrestle Kurt angle in May 1999 before he died on a Sunday night heat I believe, check it out on youtube, I watched it a while back, it wasn't anything special but was decent, shame they never had a chance to wrestle each other in their prime.
Owen hart had all the talent in the world to do something special however, something held him back, weather that be his size, or the fact his style wasn't suited for the time, either way in early 2000s he could of had some classics with Angle, Eddie, Benoit, Malenko, Jericho, just a great shame Owen died in 1999.
People keep saying about moving tna wcw etc etc, check out life and times of Owen Hart on youtube, it's a documentary by the same guy Paul Jay who did wrestling with shadows, it has Bret and Martha on, and they go into detail about how Owen was set to retire in early 2002, and that once his contract had ended he'd planned to leave wrestling for good, he only stuck to wrestling because it was fantastic money, compared to a real 9-5 job, but he actually left WWF back in 1989-1990 because he was a jobber and in Stampede he was the number one guy, and didn't like jobbing, left went to Japan created some waves and WWF rehired him, but he wasn't thrilled about high voltage tag team but it was temp, until the singles division opened up.
Owen Hart will go down has a legend that never held a World title, but you've got to remember when he was around, they're was only ONE world title, and most of the time either Bret had it (because he lived a clean lifestyle and would promote WWF all over the world) and the Kliq dominated it, he did however win the 2nd PPV version of KOTR which put Owen up to that NEW STAR level which he craved, plus his bracket in KOTR tournament was pretty good, 1 2 3 kid, Tatanka (who got a monster push 2 month later) and Razor Ramon (who was also on the fringe of the Main Event) Owen 2 month later had one of the best cage matches ever in wrestling history with Bret, probably his defining match, before being paired with Anvil who got released (Owen and Anvil were slated to win the tag titles at Royal Rumble 1995), over all I believe Owen had a lot of bad luck as far as career went, he had a stellar career but he was 7 years early, I believe he had a lot to contribute to wrestling in general, but in 1999 his style and morals weren't suited for the Attitude era, which ultimitly cost him his life, as he felt he couldn't keep saying no to storylines which he'd been doing in the months leading up to his death.