Fedor Emelianenko (world #1 ranked heavyweight MMA fighter) vs. Matt Lindland (olympic silver medal in wrestling, top middleweight MMA fighter). St. Petersburg, Russia. Fedor destroys everybody, outstriking the strikers (e.g. Cro Cop), and outgrappling the grapplers (e.g. Minotauro). And a guy more than a weight class below him is going to be a threat? I don't think so. But Ben "Dude" Curson bet me $20, and Arash bet me $50, that Lindland will win. With just even odds. Unbelievable. Result: Fedor won by armbar at 2:58 of R1. I win again.
I bet $50 on Liddell to repeat, against Arash who is betting on Tito. The main talk is that Liddell might be getting bored with winning all the time, and Ortiz is "hungry". But just looking at the skills on paper, Liddell is a bad matchup for Tito. Tito's only strategy is ground & pound, but Liddell is extremely difficult to take down (or to keep down if you manage to get him down), and his striking is far, far better than Tito's. Unless Liddell gets very lazy and just doesn't bother to train, this should be another easy victory, just like the first matchup. Result: 3rd RD TKO, Don wins.
Batata wanted a rematch from the UFC 60 bet, and had jumped on the Hughes bandwagon. But this time I thought GSP had the edge, despite the dominance Hughes had shown as long-time UFC champion. GSP was winning their first matchup (before getting caught) when he was new to MMA. And GSP had recently dominated Frank Trigg -- even in the wrestling! -- who is almost Hughes-quality as a wrestler. Result: GSP by R2 KO. I win (and Batata loses again).
Following some theoretical discussion about efficient market theory, Winfred Ark bet me that Genetech (DNA) would outperform the market averages over the next year. On 9/22/2005, DNA was $88/share (market cap $94B); DJ 10442, NASDAQ 2111, S&P500 1215. On 9/22/2006 DNA was $78 ($83B); DJ 11508, NASDAQ 2219, S&P500 1314. I won, Win lost. Stakes: loser displays a photo of winner prominently on their mantel for a year.
Royce Gracie vs. Matt Hughes, May 27, 2006, Staples Center, Los Angeles, CA. I've been a fan of Royce since the first UFC, and trained in BJJ myself since 1994. That said, Hughes had all the advantages in this matchup. I bet $100 (in two bets, vs. Arash and vs. Batata) that Hughes will win. Result: Hughes dominated and won easily, and I won the bets.
Full details are available here.
In April 2002, Overture (since acquired by Yahoo) filed a patent infringement lawsuit against Google. I bet $25 that Google would never pay a significant amount of money. I lost this bet.
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