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

By Jack McKenney

WASHINGTON, DC - MAY 18: Jake Arrieta #34 of the Baltimore Orioles pitches during a baseball game against the Washington Nationals at Nationals Park on May 18, 2012 in Washington, DC. The Orioles won 2-1 in eleven innings. (Photo by Mitchell Layton/Getty Images)
WASHINGTON, DC - MAY 18: Jake Arrieta #34 of the Baltimore Orioles pitches during a baseball game against the Washington Nationals at Nationals Park on May 18, 2012 in Washington, DC. The Orioles won 2-1 in eleven innings. (Photo by Mitchell Layton/Getty Images) /
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Trevor Bauer
ATLANTA, GA – SEPTEMBER 30: Trevor Bauer #27 of the Cincinnati Reds pitches in the second inning of Game One of the National League Wild Card Series against the Cincinnati Reds at Truist Park on September 30, 2020 in Atlanta, Georgia. (Photo by Todd Kirkland/Getty Images) /

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.

TORONTO, CANADA – JULY 26: Andrew Cashner #34 of the San Diego Padres delivers a pitch in the first inning during MLB game action against the Toronto Blue Jays on July 26, 2016 at Rogers Centre in Toronto, Ontario, Canada. (Photo by Tom Szczerbowski/Getty Images)
TORONTO, CANADA – JULY 26: Andrew Cashner #34 of the San Diego Padres delivers a pitch in the first inning during MLB game action against the Toronto Blue Jays on July 26, 2016 at Rogers Centre in Toronto, Ontario, Canada. (Photo by Tom Szczerbowski/Getty Images) /

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.

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