The 30 worst trades in MLB history

Oct 18, 2015; New York City, NY, USA; Chicago Cubs starting pitcher Jake Arrieta throws a pitch against the New York Mets in the first inning in game two of the NLCS at Citi Field. Mandatory Credit: Anthony Gruppuso-USA TODAY Sports
Oct 18, 2015; New York City, NY, USA; Chicago Cubs starting pitcher Jake Arrieta throws a pitch against the New York Mets in the first inning in game two of the NLCS at Citi Field. Mandatory Credit: Anthony Gruppuso-USA TODAY Sports /
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Jul 26, 2015; Cooperstown, NY, USA; Hall of Famer Frank Robinson waves to the crowd after being introduced during the Hall of Fame Induction Ceremonies at Clark Sports Center. Mandatory Credit: Gregory J. Fisher-USA TODAY Sports
Jul 26, 2015; Cooperstown, NY, USA; Hall of Famer Frank Robinson waves to the crowd after being introduced during the Hall of Fame Induction Ceremonies at Clark Sports Center. Mandatory Credit: Gregory J. Fisher-USA TODAY Sports /

15: Frank Robinson to the Orioles

The trade: Baltimore received Frank Robinson

Cincinnati received Milt Pappas, Jack Baldschun, and Dick Simpson

Frank Robinson established himself as an all-time legend with the Cincinnati Reds when he hit 38 home runs in his rookie season. Although the Reds would come close to winning the World Series, losing in 1961 to the Yankees, Robinson never did win a title with Cincinnati. It was only after he got dealt to the Orioles that Robinson became a 2-time World Series champion.

It was a shocking decision for the Reds to ship Robinson over to Baltimore since he was still 30 years old at the time, and still had a lot left in him. Even though Milt Pappas was a good pitcher, the backlash over the deal made it difficult for him to ever get settled in with the Reds, and he was traded after just three seasons. After the trade, Baldschun only recorded one save in his entire career.

Not only did Robinson win two World Series with the Orioles, he led the league in home runs (49), RBIs (122), and batting average (.316) becoming a Triple Crown winner in just his first season in Baltimore. Robinson has been inducted into the Hall of Fame, and his number is retired by both the Reds and the Orioles, but the botched deal – as well as him infamously calling Frank Robinson “an old 30” – forever tarnished Bill DeWitt’s legacy.

Next: 14: Pedro Martinez to the Red Sox