MLB trade deadline: The 5 worst trade deadline deals in recent history

Number 4

2021: Rays trade RHP Joe Ryan to the Twins for DH Nelson Cruz

Looking for a power bat to add at the deadline, Tampa made a move for future hall of famer Nelson Cruz, who was in the midst of an All-Star season at the time. Cruz was the sole bright spot on a struggling Minnesota team, hitting .294 with 19 homers at the time of the deal. However, he struggled to continue his excellence with the Rays. He hit just .226 with 13 homers to end the regular season, ending his tenure with drastic postseason struggles.

The AL’s top-seeded Rays were upset by the Boston Red Sox four games, with Cruz hitting .176 in 17 at-bats. To make matters worse, Cruz was merely a rental, leaving the Rays in free agency to sign with the Washington Nationals

While Cruz struggled during his tenure in Tampa Bay, dealing Joe Ryan for the veteran slugger makes the deal even tougher to swallow. Ryan was a legitimate AL Rookie of the Year candidate in 2022, tossing a 3.57 ERA in 147 innings. With a blazing hot start to 2023, Ryan looked like a legitimate Cy Young candidate at the beginning of the season. However, he’s faltered as of late, posting a 6.39 ERA over the month of July.

At 27, Ryan is still a viable young pitching piece that will be a part of this Minnesota rotation for years to come. It’s a wonderful return for a half-year veteran rental in Cruz, making this trade a huge win for the Twins.

Number 3

2019, Three-team deal: Reds acquire RHP Trevor Bauer. Indians acquire OF Franmil Reyes, OF Yaseil Puig, LHP Logan Allen, LHP Scott Moss and INF Victor Nova. Padres Acquire OF Taylor Trammell

Remember when Trevor Bauer threw a ball into center field out of frustration after getting shelled by the Royals? This iconic moment sparked a trade that would give the Reds their first Cy Young-winning pitcher in franchise history. While his 2019 season was rough with Cincinnati, Bauer bounced back during the 2020 COVID season, pitching a stellar 1.73 ERA over 73 innings pitched, leading Cincinnati to their first playoff appearance since 2013.

The trade hasn’t panned out as well for Cleveland, who expected big things from Franmil Reyes. The 23-year-old was in the midst of a 27-home run season with San Diego, appearing as a promising young bat that would excel in the lineup for years to come. Reyes had one stellar season in Cleveland, blasting 30 homers while hitting .255. Aside from that, he was largely a disappointment. Reyes struggled to make consistent contact and his power faltered. Reyes was released by Cleveland in 2022, ultimately bouncing around with a few teams, now currently apart of the Nationals minor league system.

Once a top 100 prospect with San Diego, Logan Allen was largely a bust for Cleveland, released by the team in 2022. Then there’s Yasiel Puig, who was unable to receive interest from MLB club’s after multiple serious issues. Perhaps the biggest loser was San Diego, who largely failed in developing top prospect Taylor Trammell. Trammell was later dealt in a multi-player deal that brought Austin Nola to San Diego. Though some players have yet to make debuts, this deal was a huge victory for the Reds, acquiring their first Cy Young Winner in franchise history for practically nothing.

Number 2

2016: Marlins trade RHP Luis Castillo, Josh Naylor and two pitchers to the Padres for SP Andrew Cashner and prospects

It’s hard to fathom how highly regarded of an arm Andrew Cashner was, originally brought to San Diego from the Cubs in exchange for first base prospect Anthony Rizzo. Though his first two seasons in San Diego were very strong, Cashner faltered in his fourth season and was dealt to the Marlins for this absurd haul.

Unfortunately for Padres fans, these two All-Star caliber players are no longer with the organization. Strangely enough, Castillo was reacquired by the Marlins just two days later in exchange for RHP Colin Rea, who now is a part of the Brewers starting rotation. It’s one of the most bizarre deals in recent history, with one of the best starters in our game being traded and then reacquired by his former team two days later.

As for Naylor, his numbers with the Padres were brief and rather mediocre. Naylor hit around .250 with nine homers in his stint with San Diego, and when the Padres became hungry for starting pitching, they didn’t hesitate to deal him. Naylor was apart of the deal that sent former stud pitcher Mike Clevinger to San Diego for a load of prospects.

Cashner’s time in Miami was brief and forgetful. In just 52.2, innings his ERA was just below six, and he would leave Miami to sign with the Rangers after spending a few months with the team. This trade was a clear win from San Diego, yet they failed to retain full value of the deal failing to establish Naylor and Castillo and legitimate big league pieces.

Number 1

2013: Orioles trade SP Jake Arrieta and RP Pedro Strop for SP Scott Feldman

Wow, cover your eyes, Orioles fans! While Jake Arrieta was an incredible pitcher for the Cubs and a big part of their World Series title in 2016, he was largely a disappointing and overhyped starting pitcher for Baltimore.

The Cubs capitalized on a career from Scott Feldman to acquire these eventual stars, who was similarly disappointing in Baltimore. In 15 starts with Baltimore, Feldman finished with a 4.27 ERA with 65 strikeouts, departing in free agency the following year to Houston. Arrieta went on to win the Cy Young during his 2015 season, transforming into the ace scouts long proclaimed him to be in Baltimore.

Including Strop in the deal was a bit head-straching, who was in the midst of a down year after many years of being a reliable bullpen arm with electric stuff. Strop was a key bullpen arm in the 2016 World Series run, and posted a sub-three ERA during six of his seven seasons with the Cubs.

Overall, this was an absolute fleece for Chicago that provided them key pieces for their 2016 World Series roster.