The 5 absolutely worst MLB trades in recent history

1 of 3

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.

Jul 6, 2022; Milwaukee, Wisconsin, USA; Milwaukee Brewers left fielder Christian Yelich (22) grounds out against Chicago Cubs in the first inning at American Family Field. Mandatory Credit: Michael McLoone-USA TODAY Sports /

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.

Jul 21, 2022; Houston, Texas, USA; Houston Astros designated hitter Yordan Alvarez (44) hits a home run during the first inning against the New York Yankees at Minute Maid Park. Mandatory Credit: Troy Taormina-USA TODAY Sports /

2. 2016: Astros trade RP Josh Fields to the Dodgers for OF Yordan Alvarez

We often see Andrew Friedman and the Dodgers on the right side of trades, but this one is certainly one to forget for Dodger fans.

At the time of the deal, Alvarez was just 19. The intriguing aspect of this deal is Josh Fields. It’s not like the Dodgers were trading for a Mark Melancon or Roberto Osuna-type closer, Fields was actually quite below average when the Dodgers acquired him. With Houston in the season he was dealt (2016), Fields had a 6.89 ERA but was clearly catching unlucky breaks with 2.83 FIP.

To make Dodger fans feel better, I’ll include that, in three seasons with Los Angeles (2016-18), Fields had a sub-three ERA every year, showing very reliable consistency. But I don’t think that little snippet cures the sadness Dodger fans have who imagine a potential lineup with the big Cuban slugger included.

1. 2016: White Sox trade RHP Erik Johnson and SS Fernando Tatis Jr. to the Padres for SP James Shields

White Sox fans have to be shuddering to see this nightmare of a deal.

In 2016, after the Padres season went completely south and were 11.5 games back of first (in early June), they decided to unload Shields while they could. The veteran righty was coming off a World Series win the previous season, as he emerged as the Kansas City ace late in the postseason. The White Sox were very interested in Shields; interested enough to take on his four-year, $75 million deal. The Padres absorbed $31 million of his salary in order to soften up the contract load.

Many people questioned why they would take on so much money for two prospects? Well, one of those prospects included a kid named Fernando Tatis Jr, now known as “El Nino.” Arguably the best and most exciting player in baseball, Tatis will be the face of San Diego’s franchise for years to come.

Next. The 10 likeliest players moved at the MLB trade deadline. dark

Though Preller and the Padres completely failed in building up their team to win in 2016, they did come out of the mess with a potential Hall of Famer and MVP.

Home / MLB News