The top 5 Worst MLB Trade Deadline Trades of All Time
By Oliver Wiener July 31, 2024 11:14
As the MLB trade deadline approaches each year, teams scramble to make deals that will either gear them up for a postseason push or bolster their rosters for future success. This frenetic period is characterized by high-stakes gambles, with general managers playing a complex chess game, hoping to come out on top. However, not all trades turn out as planned.
In this feature, we'll dive into the top 5 worst MLB trade deadline trades of all time, exploring the decisions that left a lasting mark on the franchises involved for all the wrong reasons.
1. Red Sox trade Jeff Bagwell for Larry Andersen
Teams Involved
- Boston Red Sox
- Houston Astros
- Players Traded
- Jeff Bagwell (to Houston)
- Larry Andersen (to Boston)
- Year of Trade 1990
Analysis
In one of the most lopsided trades in baseball history, Jeff Bagwell was dealt from the Boston Red Sox to the Houston Astros for Larry Andersen. In those days, the Red Sox needed to improve their bullpen for a playoff run, and Andersen was a talented arm. But they dealt Bagwell, who would become a Hall of Famer and arguably the best hitter in his prime.
Both players enjoyed great careers in Houston, with Bagwell's 15-year tenure going down as one of the best in history for a player that spent all their playing days at four corners favorite. He compiled a career WAR Wins Above Replacement of 79.9, as opposed to Andersen's paltry 3.8 over his time with the Sox. The trade that sent Bagwell, then a highly regarded minor leaguer, to the Astros was made worse because he won 1991 Rookie of the Year and became part of four All-Star teams.
The impact that Bagwell had on the Astros was immense, as he led them through many playoff runs and finally, in 2017, was enshrined into The Hall of Fame.
2. Mets Trade Scott Kazmir for Victor Zambrano
Teams Involved
- New York Mets
- Tampa Bay Devil Rays
- Players Traded
- Scott Kazmir (to Tampa Bay)
- Victor Zambrano (Traded to the New York Mets)
- Year of Trade 2004
Analysis
The New York Mets made what would be the most memorable trade of their history by sending away top pitching prospect Scott Kazmir, for an ineffective wild pitcher in Victor Zambrano. At the time, the Mets were searching for starting help, while Zach Zambrano may have been a disappointment that year.
Kazmir became an All-Star and a linchpin of the Rays' resurgence. He amassed a career WAR of 34.5 and played an essential role in the Rays' pennant-winning year (2008). The Mets' choice to deal with Kazmir, who would go on to have a productive career, was an awful calculation, and it cost them their ace and perhaps more than that in the midst of one theirs harvested squandered all opportunities years.
The Mets would feel the effects of this trade for years to come as they had difficulty coming up with reliable pitching, while Kazmir turned into a central figure in Tampa Bay. It has been used as a cautionary tale about trading young talent for the benefit of right now.
3. Chris Sale to Boston
Teams Involved
- Chicago White Sox
- Boston Red Sox
- Players Traded
- Chris Sale (to Boston)
- Year of Trade 2016
Analysis
While the Sox got their coveted minor leaguer in Moncada, Sale's trade value was most evident with a World Series championship from Boston two years later.
Sale was one of the top, most dominating pitchers in baseball. His time in Boston eventually led to a World Series championship for the Red Sox, with whom he was an important part of their rotation. Moncada, meanwhile, has taken longer to develop, and although he can be worked if he's hot when he's good, there might not be a position player in the organization on par with what they had.
The White Sox dealt Sale as part of a larger rebuilding strategy, but it makes one wonder if they could have been better and retained him while retooling the roster in virtually every other way. It's just a reminder of how beautiful and fragile that line is between rebuilding and dealing away franchise cornerstones.
4. Adrian Gonzalez for Ugueth Urbina
Teams Involved
- Miami Marlins
- Texas Rangers
- Players Traded
- Ugueth Urbina (to Miami)
- Year of Trade 2003
Analysis
The Miami Marlins traded future star Adrian Gonzalez along with another two players to the Texas Rangers in a trade that would surely give them nightmares for Ugueth Urbina. Urbina was a quality reliever at the time as he helped earn the Marlins their second World Series title that season.
In the first overall selection of the 2000 draft, Gonzalez became a five-time All-Star and one of MLB's most reliable hitters. Ultimately, the Marlins trading him away for short-term gain resulted in one of their best prospects turning into a cost-controlled future star who would have had an enormous impact on their franchise.
The Marlins will have to bear the consequences of trading young talent for experienced arms in a short-sighted move.
5. Ben Zobrist for Aubrey Huff
Teams Involved
- Houston Astros
- Tampa Bay Devil Rays
- Players Traded
- Traded Ben Zobrist and RHP Mitch Talbot to Tampa Bay.
- Aubrey Huff (to Houston)
- Year of Trade 2006
Analysis
The trade that swapped Ben Zobrist and Mitch Talbot for Aubrey Huff to the Tampa Bay Devil Rays is another mistake on behalf of a team reading talent wrong. The Astros needed power then and traded for Huff, who had a good track record. Huff did little to help in Houston, producing only 0.2 WAR during his brief stay with the team.
Zobrist, however, had an excellent career; he became a utility player and played on winning ball clubs. Trading Zobrist when he was still a work in progress for the short-term rental of Huff is often mentioned as one of their biggest blunders. It's an object lesson in identifying and properly cultivating youth.
Baseball is littered with trades that have haunted franchises for years, highlighting that it can risk misjudging talent or overvaluing immediate benefits at the expense of long-term potential to feature some of the worst trades in baseball history.
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