10 Hilariously Horrible MLB Trade Deadline Deals (That Made Other Teams Look Like Geniuses)
Ah, the MLB Trade Deadline. That magical time when GMs either look like absolute wizards or... complete clowns.
Some trades are legendary because they helped win World Series titles. Others? They’re legendary for all the wrong reasons—like when a team gives away a future MVP for a middle reliever who lasts two weeks and a pulled hamstring.
Let’s take a look at 10 of the worst trade deadline deals in MLB history, a.k.a. “How to Build a Dynasty… for Someone Else.”
1. Red Sox Give Astros a Hall of Famer for a Rental Reliever (1990)
Boston gets: Larry Andersen
Houston gets: Jeff Freakin’ Bagwell
Boston needed a bullpen boost. They got Andersen for, like, a month. The Astros? They got a guy who would hit 449 bombs, win an MVP, and make the Hall of Fame. Bad trade? That’s putting it lightly. This was a full-on baseball heist.
2. Tigers Gift the Braves a Future Ace (1987)
Detroit gets: Doyle Alexander
Atlanta gets: John Smoltz
Alexander was good—he went 9-0 down the stretch. But the Tigers missed the World Series and gave up Smoltz, who just casually became a Cy Young winner, World Series champ, and a Hall of Famer. It’s like trading your house for a one-night stay at a nice hotel.
3. Brewers Trade Hader Mid-Playoff Hunt (2022)
Milwaukee gets: Some guys
San Diego gets: One of the best closers in the game
The Brewers said, “Let’s shake things up!” and promptly missed the playoffs. Hader? Became a dominant closer again with the Padres. Fans are still trying to figure out what the plan was here. Milwaukee, blink twice if you regret this.
4. Red Sox Deal the Farm for Chris Sale’s Elbow (2016)
Boston gets: Chris Sale
Chicago gets: Yoán Moncada, Michael Kopech, etc.
To be fair, Boston did win a World Series with Sale. But they also gave the White Sox two cornerstone players. Sale eventually turned into an injury update waiting to happen. Meanwhile, Chicago got younger, cheaper, and healthier. Whoops.
5. Dodgers Ship Off Carlos Santana Before He Could Rock Cleveland (2008)
LA gets: Casey Blake
Cleveland gets: Carlos Santana (the catcher, not the guitarist—but both have hits)
The Dodgers were chasing October and decided a 34-year-old third baseman was the missing piece. Meanwhile, Cleveland ended up with a switch-hitting slugger who played a decade of solid baseball. LA really fumbled the bag here.
6. A’s Let McGwire Go for… Names We’ve All Forgotten (1997)
Oakland gets: T.J. Mathews and some dudes
St. Louis gets: Mark “Home Run Show” McGwire
McGwire hit 70 homers a year later. The guys Oakland got? Great trivia question answers—if anyone remembers them. The A’s basically handed the Cardinals a media sensation and got a bag of peanuts in return.
7. Cubs Trade Kris Bryant for Hope and Vibes (2021)
Chicago gets: Prospects (still TBD)
San Francisco gets: Kris Bryant
Bryant came in hot and helped the Giants win 107 games. The Cubs got a couple of lottery tickets. So far, they’ve scratched off nothing but “Try again.” Fans still wear their Bryant jerseys and whisper “Why?” into the wind.
8. Mariners Give Up Randy Johnson Before He Becomes Terrifying (1998)
Seattle gets: Garcia, Guillen, Halama
Houston gets: The Big Unit
Seattle traded away one of the scariest pitchers ever, and he immediately threw a 1.28 ERA for Houston. The Mariners did okay with the return, but trading a guy who would throw a no-hitter at age 40? That’s tough to spin.
9. Nats Send Two Studs to Chicago for a Banged-Up Adam Eaton (2016)
Washington gets: Adam Eaton
White Sox get: Lucas Giolito, Reynaldo López, Dane Dunning
Eaton blew out his ACL after a hot start. Meanwhile, the White Sox built half their pitching staff from this one trade. The Nationals eventually won a title, so we’ll call this one a chaotic neutral, but yeah… not great.
10. Pirates Pull Off a Masterclass in What NOT to Do (2018)
Pittsburgh gets: Chris Archer
Tampa gets: Tyler Glasnow, Austin Meadows, Shane Baz
This one’s so bad it’s almost funny (unless you're a Pirates fan, then it’s just painful). Archer was mid at best. Tampa? They got two All-Stars and a top pitching prospect. It was like trading gold bars for a handful of magic beans… and then the beans didn’t even sprout.
Closing Time:
These trades are proof that baseball GMs are just like the rest of us: sometimes, they make really bad decisions under pressure. The only difference? Their mistakes haunt franchises and show up in ESPN graphics for the next 20 years.
Got a trade that still gives you nightmares? Drop it in the comments. Misery loves company.