Without attempting to turn this into another frantic anti-Dempsey tirade, I agree with senya. Of course Dempsey's chances would increase if he makes it past the mid-distance, he might even win a few early ones, but Tua's superior durability and strength would count for a lot IMO. I think Tua will catch him pretty early on and Dempsey fails to clear the cobwebs, hanging in there until approaching the mid-rounds when a big left hook ends it. Tua TKO5.
I think if Dempsey can make it through the first round he could win a points decision but I am also a fan of Tua and Dempsey's aggressive style suits Tua so it may not last long, hard one to call.
A dive, where Dempsey made up a false story in his auto-bio of being knocked down three times during about 2 minutes of fighting, and his brother throwing up the towel?
I've read at least 5 different versions of what happened in that fight. Dempsey himself has told a few different tales regarding that fight, that doesn't prove anything one way or the other. The evidence that it was a dive is very convincing, and Dempsey had more than enough motive to take a dive at that point of his career.
What motive could that be? I have a next-day report from Salt Lake Telegram, as well as the reports leading up to that fight. Dempsey rushed, but was caught by a well-placed hook on the point of the jaw. The same way Flynn himself was knocked out by Sam Langford, he learned from that fight, and executed the same trick.
I'd go with Tua as well. I don't think Dempsey was either good or smart enough to box Tua. He'd get into a fight with someone who has a harder chin, more powerful punch and better workrate. Tua KO 4 in a great fight.
It's worth noting that Monte Cox in his article doesn't even raise a question of who and why would pay Dempsey $500 for a dive with Jim Flynn. The show didn't sell well that night. As for the delay before the start of the main event, it wasn't the first time it happened in that place, as can be seen in local reports from that time, there were often long delays between bouts for one reason or another.
http://www.ibroresearch.com/Articles/The%20Early%20Jack%20Dempsey/THE%20EARLY%20JACK%20DEMPSEY.htm Even if the knockout was legitimate, Dempsey was basically a hobo at the time of the bout. Taking into account the fact that it was an isolated incident, and the question marks surrounding the fight, I'm not willing to consider it very seriously when judging Dempsey or the quality of his chin.