UPDATE: This poll is now closed.
For our second match in Round One, Rockies GM Dan O'Dowd (11) faces J.P. Ricciardi (6) of the Jays. Bill Smith vs. Jon Daniels is still open; that match will close once the next poll goes up.
Both of these may seem like odd choices - after all, the Rockies are the defending N.L. champs, and Ricciardi was once a sabermetric darling who worked under Billy Beane. But they both belong here. O'Dowd bumbled around for years, signing Mike Hampton to a horrific contract, playing Neifi Perez and wringing his hands about how to win at altitude without bothering to try the unconventional idea of just putting good players on the field. O'Dowd and the Rockies racked up six straight losing seasons between 2001 and 2006. In his defense, he's got a decent core of young talent, and there's that World Series.
As for Ricciardi, the beginning of his tenure was characterized by the worst aspects of "Moneyball" - not spending money, and drafting college players. The former wasn't really his fault, but the latter certainly was. Ricciardi only got David Bush and the disappointing Russ Adams in his first draft, in 2002. In 2003 he got Aaron Hill and Shaun Marcum. His 2004 draft wasn't any better, and his 2005 draft, in which he took Ricky Romero with the sixth overall pick with numerous future stars still on the board (O'Dowd grabbed Troy Tulowitzki one pick later), was just awful. The Romero pick was especially uninspired - why reach for a low-upside college arm when you can have Tulowitzki or Cameron Maybin or Jay Bruce? Ricciardi's ultra-conservative approach in the draft has utterly failed to produce stars (if 2006 top pick Travis Snider makes it, he'll be the first), and how are you supposed to knock off the Yankees and Red Sox without stars?
In his defense, the Jays under Ricciardi have never been bad. Also, Ricciardi has eased up on the college-first draft philosophy in the last two years, and ownership has given him some money to work with. Regrettably, Ricciardi has used that money to do as much as any mid-market GM to run up salaries for free agents, notably dumping $47 million on reliever / injury magnet B.J. Ryan. Many of Ricciardi's trades and signings have been fine in isolation, but most of them would have made a lot more sense if the Jays were just a player or two from finishing first, which they aren't and haven't been. Or perhaps Ricciardi's happy to come in third? Without an infusion of talent, he may not continue to be able to achieve even that modest goal - Tampa Bay is breathing down his neck.