Every year DDD and I drive up to LABR together to draft the RotoWire teams, and every year we wind up making some bets. Here's last year's post of the same title, which incidentally is one of the first things that comes up when you google him. Even though he won five out of six, most people probably won't bother to click through and just think he's an idiot due to the title. (If they did click through they'd see I took Plaxico Burress over Brandon Marshall with one of them). Incidentally, I actually won money from him last year due to a couple football league side bets, even including my 1-5 showing on his foolish ones.
Here are the ones for this year:
Made before the NBA season: DDD has Cavs, Lakers, Spurs, Celtics to win NBA title. I have the field for $20. I'm getting 6:1.
I've got Johan Santana for $20 vs. Cole Hamels (better fantasy season).
I've got Santana vs. Tommy Hanson (better fantasy season).
I've got Rashard Mendenhall vs. Jamal Charles $20 - better fantasy season.
After DDD bought Stephen Strasburg for $9 in NL LABR, I bet him he'd be "subjectively happy" with that purchase by season's end. Also $20.
I don't really care who wins - the most important thing is to keep him associated with "foolish bets" when people search for him.