When 'Dealin' Dan O'Dowd chose Brad Pitt, err Billy Beane to be his trade partner in 2008, there was concern that O'Dowd had no chance of gettting the better end of the deal with the Moneyball originator. Five years later, a full review of all of the players traded can show how it turned out.
While I was and still am a fan of Matt Holliday, I completely understood in 2008 why he was not likely to remain a Colorado Rockie for life. He and his agent, Scott Boras, were interested in playing the free agent market and seeing what kind of deal he could get. However, trading with the A's during the off-season seemed a tad cowardly as a deadline deal might possibly get more in return and if Billy Beane was willing to make the trade then what did he know that the Rockies front office didn't know?
The A's, like the Rockies, were not likely to land Matt Holliday long term. The only reason they would make this trade then, is to get a good half of a year out of him and get more in return at the deadline than they gave up to the Rockies in the first place. What they gave up though seemed to be quite a lot, with a future high-ceiling outfield in Carlos Gonzalez, an established closer in Huston Street, and a lefty starting pitching prospect in Greg Smith.
Since the trade, Matt Holliday has been worth a combined 22.3 fWAR, although not even three of that was for the Athletics. Gonzalez, over the same time has been worth 14.9 fWAR, with Huston Street providing a total of 4.3 fWAR (1.1 with the Padres last year), and Smith giving the Rockies 8 starts in 2010 with no WAR benefit.
While not the perfect statistic to compare a trade, the Rockies seemed to get about equal value at a much reduced price level and have a younger player with a team-friendly contract that will likely be better in the long run. But, the A's didn't keep Holliday past the 2009, trade deadline, instead choosing to ship him to the Cardinals for three players to presumably replace what they lost to the Rockies with better talent and a lower cost.
So would the Rockies have been better off, waiting for this trade themselves? The A's acquired one of the Cardinals top prospects in third baseman Brett Wallace, outfield prospect Shane Peterson, and starting pitching prospect Clayton Mortensen. They ended up turning two of these players in other trades, getting outfielder Michael Taylor from the Blue Jays for Brett Wallace, and trading Mortensen to the Rockies for Ethan Hollingsworth.
Showing that they will trade more than even Dealin' Dan, the A's then sent Hollingsworth to the Royals for Kila Kai'aihue. At the same time, the Rockies were not done trading as they sent Street to the Padres for Nick Schmidt when he became too expensive and they had a solid replacement in Rafael Betancourt.
The end fall out still is not over as some of these players are still in the minor leagues, but a little more than four years later, the trade works out to:
Oakland A's: 6 months of Holliday (~2 fWAR); OF Shane Peterson (age: 25, L/L, AAA in 2012); OF Michael Taylor (age: 27 R/R, a cup of coffee in MLB in 2011 and 2012); 1B Kila Kai'aihue (age: almost 30, L/R, .1 fWAR in 39 games last year)
Colorado Rockies: OF Carlos Gonzalez (age: 27, L/L, starter since 2009 with 14.9 fWAR); 3 years of P Huston Street (3.2 fWAR); 1/2 a year of P Greg Smith (0 fWAR); P Nick Schmidt (age: 27, L/L, in AAA last year)
While the A's still have a chance of one of their two outfielders exploding to make this a more balanced trade, it appears for now that Dan O'Dowd pulled one over on his friend Billy Beane. Let us hope that Cargo continues his great hitting and his underrated defense in order to make this trade, one of the worst ten in A's history according to Bleacher Report, look even worse as we look back five years from now.