The Matt Holliday trade (Nov. 10, 2008)

The trade: The Colorado Rockies traded Holliday to the Oakland Athletics for OF Carlos Gonzalez, LHP Greg Smith and RHP Huston Street.

How it happened: Holliday wasn’t quite the all-around player that Machado is; he never had much of a glove, playing a passable (at best) left field. But, boy, the guy could hit, even accounting for the Coors Field bump that inflated his home stats. Holliday was a three-time All-Star and was the NL MVP runner-up in 2007, when he hit .340 with a 1.012 OPS, 36 homers and 137 RBIs. Holliday, a Scott Boras client, was unlikely to re-sign in Colorado when he reached free agency after the 2009 season.

The low-spending Athletics were a surprising trade match for Holliday, as they didn’t stand a chance of signing him, either. But they hoped he would jolt an Oakland offense that scored the fewest runs in the majors the previous season. They paid a hefty price to find out, giving up five-tool rookie outfielder Gonzalez as well as their closer, Street, and their team leader in starts in 2008, Smith.

The results: The trade will go down as one of the worst in Billy Beane’s history as Oakland’s general manager. While Smith was no loss — he made only eight starts for Colorado — Street served as the Rockies’ closer for three years.

Even if those two players hadn’t been involved, though, giving up Gonzalez alone for Holliday was a giant mistake. Gonzalez spent the next nine seasons as a mainstay in the Rockies’ lineup, amassing a 22.9 WAR over that span and finishing third in NL MVP voting in 2010.

Holliday, meanwhile, never seemed to fit in with the Athletics. Moving from hitter-heaven Coors to spacious Oakland Coliseum dampened his offensive numbers, and with the A’s languishing in last place in late July, they flipped Holliday to the St. Louis Cardinals. He spent the next eight years in St. Louis, making four All-Star teams. The prospects the Athletics received in the second Holliday trade weren’t anywhere near as productive as the players they gave up to acquire him. Beane came out on the losing end of the Holliday experiment.

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