The Biggest Trade Deadline Deals in MLB History

The July trade window in MLB is known to be short, so teams must make their new player deals and decisions in time before the window ends. Within this time, some teams trade players to improve their team’s overall roster while possibly making extra revenue.

In the history of the MLB, we’ve seen some dramatic deals go down, and right toward the end of the trade window. Without further ado, let’s dive into the biggest trade deadline deals in MLB history, including what players were part of the deadline trade, what teams they were traded to and the impact that player had on their new team for that season.

5. Mark Teixeira to the Angels – July 29, 2008

As big news back in July of 2008, Mark Teixeira, one of the best hitters in MLB, was traded just in time to the Angels before the July trade window ended. Not only was this transfer last second, but it was vital to the Angels’ success that season. In 54 games for the Angels, Teixeira had scored 13 home runs and had a batting average of .358 along with an on-base percentage of .449. In the end, he’d help the Angels advance to the American League Division Series against the Boston Red Sox, scoring four runs throughout the series. In addition to the Angels losing that series, they’d also lose Teixeira that next season to the New York Yankees.

4. Randy Johnson to the Astros – July 31, 1998

Despite how important the trade of Randy Johnson to the Astros was during the 1998 season, the Astros would still fail to win the World Series. Although the results weren’t what they wanted, Johnson made a massive impact in Houston for the two months he was on the team. Johnson went 10-1 with a 1.28 ERA after first being traded to the Astros. He only allowed 12 runs out of 57 hits as a pitcher with 116 thrown strikeouts in just 84 innings to seal the deal. This truly is remembered in MLB history, as the Astros that season would go on to win 102 games with Johnson’s last-second signing. To add even further to the legend, Johnson would go on to rack up the second most strikeouts in MLB history by the end of his career.

3. Carsten Charles Sabathia to the Brewers  – July 7, 2008

Another crazy July 2008 trade that made noise around the MLB was CC Sabathia getting traded to the Brewers in exchange for Matt LaPorta, Zach Jackson, Rob Bryson and one other player to the Guardians. This trade turned out to be beneficial for both teams, especially considering the Brewers had not seen an MLB postseason since 1982 until Sabathia showed up. Over 130 innings in 83 games, CC Sabathia threw seven complete games and three shutouts, allowing just 24 runs overall in stemming from the quick deadline trade. While the Brewers would eventually be knocked out of the playoffs by the Phillies, Carsten Charles Sabathia made an impact in what was a huge move on the last day of the deadline. 

2. Manny Ramirez to the Dodgers – July 31, 2008

In his move from the Boston Red Sox to the LA Dodgers, Manny Ramirez sparked a lot of controversy, with his especially negative attitude toward the Red Sox before leaving. Some of his antics included faking a knee injury since he did not want to play for his team anymore. Regardless, the 2008 mid-season trade window was wild that season, especially for Ramirez, scoring 17 home runs to help the Dodgers win the NL West. Then, in the playoffs, Ramirez had an absurdly-high .520 batting average, only losing to a future world-champion Phillies team later that year.

1. Yoenis Céspedes to the Mets – July 31, 2015

Out of all of the trade deadline deals in MLB history, Yoenis Céspedes takes the cake when it comes to dramatic swaps. In what originally was a null-trade epidemic for the sought-after Carlos Gomez, Céspedes would on the final day of the July trade window be transferred to the New York Mets as a last-second substitute. That season, Céspedes was a godsend deadline trade for the Mets, scoring 17 home runs, 10 doubles and three triples with an on-base percentage of 1.048. The value the Mets received out of this trade on such short notice makes it one of the biggest trade deadline deals in MLB history for sure.