MLB Trade Deadline: Top 25 midseason deals of all-time

5a. Red Sox acquire Jake Peavy, July 30, 2013

5b. Giants acquire Jake Peavy, July 26, 2014

Jake Peavy was once one of the best pitchers in baseball, winning the NL Cy Young Award as a member of the San Diego Padres in 2007 in a dominant season that included the pitching Triple Crown. Peavy led the league in wins (19), ERA (2.54) and strikeouts (240), and finished seventh in the MVP vote.

Two years later, Peavy was traded to the Chicago White Sox, in the first of three trade deadline deals involving the right-hander. Peavy was terrific in three starts with the White Sox in 2009, but struggled with injuries in his first three years in Chicago. After an All-Star season in 2012, followed by a slow start in 2013, Peavy was traded to the Red Sox.

Peavy made two postseason appearances with the Padres, both losses in the NLDS in 2005 and 2006, respectively. He never pitched in the playoffs with the White Sox, but made an impact in Boston. In his first postseason start with the Red Sox, Peavy allowed just one run in 5.2 innings against the Rays. Boston won the decisive Game 4. Peavy started once in the ALCS and in Game 3 of the World Series. He tossed four solid innings in his Fall Classic debut, and though the Cardinals won the game in walk-off fashion, Boston won the series.

The Red Sox imploded in 2014, and were out of playoff contention by the trade deadline. As a result, Boston sent Peavy to San Francisco. The veteran right-hander was 6-4 with a 2.17 ERA in 12 regular season starts with the Giants after the trade, and picked up his only postseason win with 5.2 shutout innings against the Nationals in the NLDS. Though Peavy struggled the rest of the postseason, he helped the Giants win the World Series, giving him rings in back-to-back seasons after back-to-back trades at the deadline.