The 5 absolutely worst MLB trades in recent history

MLB trade season is officially upon us!

In honor of the MLB Trade Deadline, let’s take a look back at some of the worst trades in recent MLB history, some of which occurred at the deadline.

5. 2018: Dodgers send OF Yasiel Puig, SP Alex Wood, OF Matt Kemp, and IF Kyle Farmer to the Reds for SP Josiah Gray, 2B/SS Jeter Downs, and SP Homer Bailey

Yes, obviously this was a brutal trade for the Reds that didn’t make much sense. The Dodgers basically dumped a bunch of washed veterans and Yasiel Puig for some diamond in the rough prospects. However, perhaps the more impressive feat of this trade is how the Dodgers were able to turn Downs and Gray into such coveted assets.

At the time of the deal, Downs and Gray were the number #7 and #20 prospects in a mediocre Reds farm system. Through the Dodgers’ incredible player development, Gray and Downs were developed into top 100 prospects (according to MLB pipeline).

However, the Dodgers had no plans for these two to suit up in Dodger blue. Instead, Downs was the centerpiece of a deal along with Alex Verdugo and Connor Wong that brought former MVP and future Hall of Famer Mookie Betts to Los Angeles. A few seasons later, Gray, along with top-catching prospect Kiebert Ruiz and two other minor leaguers, was sent to the Washington Nationals in exchange for infielder Trea Turner and starting pitcher Max Scherzer.

It’s incredible to think how the Dodgers were able to acquire Gray and Downs at a relatively small cost, and then flip them for some of the best players in our game.

Though this is quite tough for Reds fans to swallow, some good did come out of this blockbuster deal. Yasiel Puig was later shipped to the Indians in the deal that brought future Cy Young winner Trevor Bauer to Cincinnati. Let’s also not forget infielder Kyle Farmer, who has established himself as an everyday player in the Cincinnati lineup this year.

4. 2018: Marlins trade OF Christian Yelich to the Brewers for OF Lewis Brinson, OF Monte Harrison, IF Isan Diaz, and RHP Jordan Yamamoto

After the 2017 season and an ownership change, the Marlins decided to change direction and rebuild. After trading reigning MVP Giancarlo Stanton and budding young star Marcell Ozuna, it was only logical to deal Yelich as well.

The one thing that really irked me about this trade was the imaginary time clock that seemed to be at play within the Marlins front office. After moving Ozuna, Stanton, and Dee Gordon, the Marlins seemed determined to liquidate all of their assets before the season began. But why? Ideally in a rebuild, you want to move your assets when they are at their highest value.

Regardless, in return for Yelich the Marlins received outfielder Lewis Brinson, infielder Isan Diaz, outfielder Monte Harrison, and pitcher Jordan Yamamoto. Brinson was the prize of the deal and, at the start of the 2018 season, the Marlins wanted to show off their new asset by penciling him in the Opening Day lineup. However, this was a huge mistake as Brinson slashed a .199 batting average with 11 homers. This miserable stat-line further proved rival scouts correct, as many were concerned with Brinson’s ability to hit breaking balls. Brinson never found his stride as a Marlin and was released late last season.

The same goes for Jordan Yamamoto, who had some great starts early but then was cut after having an 18.26 ERA in 2020. Isan Diaz hit .193 for the Marlins last year and was cut. Monte Harrison is now a backup outfielder on the Angels.

As for Yelich, well, he became the face of the Milwaukee franchise. In 2018, Yelich broke out with a career year, hitting .326 with 36 homers on his way to earning NL MVP. The following season, he topped that mark hitting .329 with 44 homers and finished second in MVP voting.

Though Yelich has certainly cooled down in recent years, he still remains a cornerstone player within the organization and will lead the team for years to come. As for the Marlins, well, I’m afraid their organization was a victim of something called legal robbery.

3. 2018: Pirates trade RHP Tyler Glasnow, OF Austin Meadows, and RHP Shane Baz to the Rays for SP Chris Archer

This trade will truly go down as one of the great trade deadline heists.

In 2018, the Pirates were still in the Wild Card chase and had a lot of pressure from the fanbase and media to be buyers at the trade deadline. The Pirates caved into this pressure and went all in for their postseason run by acquiring multiple reinforcements with Rays starting pitcher Chris Archer being the most notable. In exchange, the Pirates gave up former top prospects in outfielder Austin Meadows, pitcher Tyler Glasnow, and a PTBNL.

It’s important to note that Glasnow had little success with the Bucs at the big league level, despite his highly touted prospect status. However, by tweaking his mechanics, the Rays turned Glasnow into an absolute stud. By only throwing from the stretch in a new fluid motion, Glasnow gained fastball velocity and developed a nasty 12/6 curve.

As for Meadows, he actually had pretty solid numbers for the Bucs. In the season he was traded (2018), he hit .292 with five homers. In 2019, Meadows started raking on an elite level, hitting .291 with 33 homers, earning his first All-Star Game trip.

Oh yeah, and then there was that PTBNL, who turned out to be Shane Baz. The Rays developed him into an absolute stud and, coming into this season, Baz was the 16th overall prospect (according to MLB Pipeline). Baz is out for the season, but remains one of Tampa’s most promising young arms.

The Pirates really did get fleeced. To make matters even more depressing, the Pirates missed the playoffs and Archer pitched 52 innings with a less than impressive 4.30 ERA. The following season Archer’s ERA climbed to 5.19, and he was eventually released. It’s arguably the worst trade in Pirates history.