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The 10 Best August Waiver Trades in MLB History

Big trades don’t just happen in July. 

The Angels made a splash on Thursday by acquiring All-Star outfielder Justin Upton from the Tigers in the most significant waiver trade of the season. August trades are infrequent, and less frequently significant. You get plenty of deals like the Yankees acquiring 37-year-old minor-league catcher Erik Kratz, but deals as significant as the Upton one are rare—rare enough, in fact, that we felt inspired to look at 10 of the best. 

10. Twins acquire David Ortiz

The only reason this trade is important is that it gave Minnesota the chance to screw up and release Big Papi six years later. Oops. 

9. Delmon Young to the Tigers

The third stop in Delmon Young’s strange MLB career was Detroit, where he landed in a trade with the Twins on Aug. 15, 2011. His numbers in the regular season were pedestrian but Tigers fans (and Yankees fans) will definitely remember what he did in the 2011 and 2012 postseasons. Young played a key role in Detroit’s 2011 ALDS win over the Yanks and a bigger part in vanquishing New York in the 2012 ALCS, a series in which he was named MVP.

8. Angels pick up Justin Upton

It may seem early to rank this among the most impactful August trades in history but hear me out. Mike Trout has absolutely no help in the Anaheim lineup. Judging by OPS+, the only other above-average hitters on the Angels’ roster this year are C.J. Cron and Andrelton Simmons. It’s miraculous they’re in the AL Wild Card hunt, given how thin the team's lineup has been. Upton could be the bat the Angels need to battle for the division in the future. 


7. Padres acquire Brian Giles

This is an interesting one. Neither the Pirates nor the Padres were contenders when this trade was executed in August of 2003. Giles was one of the best hitters in the NL and the Padres gave up two brand-name players (Oliver Perez and Jason Bay) to get him. A solid trade all around. 

6. Cardinals get Larry Walker

The Cards picked up Larry Walker on Aug. 6, 2004 for essentially nothing—all three of the guys St. Louis sent back to Colorado never played a single game for the Rockies—and all they got in return was a borderline Hall of Fame hitter who helped lead them to a World Series. 


5. Jays add David Cone for World Series run

The Mets weren’t doing much in 1992 so they decided to trade ace pitcher David Cone to the Blue Jays. Cone was strong down the stretch for Toronto and the Jays won each of his two starts in the World Series. The Mets got Jeff Kent in return, who wasn’t the same Jeff Kent we saw with the Giants and Astros but was still a decent player. 

4. Jose Bautista goes north

Joey Bats had a tumultuous early career but finally managed to stick with the Pirates for almost five years. When he was moved to the Blue Jays on Aug. 21, 2008, it seemed like a minor deal. Two years later he hit 54 home runs. 

3. Astros acquire Jeff Bagwell

Larry Andersen pitched 22 innings of strong relief for the Red Sox in 1990 but Boston had to give up a 22-year-old prospect named Jeff Bagwell to get him. Andersen signed with the Padres as a free agent before the 1991 season. Bagwell won Rookie of the Year that season and went on to become a Hall of Famer. 


2. Braves score John Smoltz

The Tigers got a steal in the 1985 draft, picking up local product John Smoltz in the 22nd round. In August of 1987 they traded him to the Braves for an aging pitcher named Doyle Alexander, who went 9–0 down the stretch for Detroit and helped the Tigers edge the Blue Jays for the AL East crown in the pre-wild card era. Alexander led the majors with 18 losses for the Tigers in 1989, the same year Smoltz, a future Hall of Famer, made his first All-Star team. 

1. Dodgers break the bank

There have been more important trades in August but never one as expensive. Aug. 25, 2012: Adrian Gonzalez, Josh Beckett, Carl Crawford and Nick Punto go from the Red Sox to the Dodgers; Boston receives James Loney and four others. The trade allowed the Red Sox reset their entire roster by clearing $270 million in future payroll obligations. The Red Sox cashed in a year later by making a few additions en route to winning the 2013 World Series.