Top 25 MLB trades of all time

NEW YORK, NY - APRIL 09: Pitcher Noah Syndergaard #34 of the New York Mets delivers a pitch against the Miami Marlins during the first inning of a game at Citi Field on April 9, 2017 in New York City. (Photo by Rich Schultz/Getty Images)
NEW YORK, NY - APRIL 09: Pitcher Noah Syndergaard #34 of the New York Mets delivers a pitch against the Miami Marlins during the first inning of a game at Citi Field on April 9, 2017 in New York City. (Photo by Rich Schultz/Getty Images) /
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CIRCA 1960s: Outfielder Frank Robinson #20 of the Baltimore Orioles at the plate getting signals from the 3rd base coach during a circa late 1960s Major League Baseball game. Robinson played for the Orioles from 1966-71. (Photo by Focus on Sport/Getty Images)
CIRCA 1960s: Outfielder Frank Robinson #20 of the Baltimore Orioles at the plate getting signals from the 3rd base coach during a circa late 1960s Major League Baseball game. Robinson played for the Orioles from 1966-71. (Photo by Focus on Sport/Getty Images) /

10. Frank Robinson to the Orioles, 1966

  • Orioles get: Frank Robinson
  • Reds get: Milt Pappas, Jack Baldschun, Dick Simpson

The Baltimore Orioles of the early 1960s were a very solid team, but were one piece short of being a true contender for the World Series. The addition of Frank Robinson changed all that. Coming over from the Cincinnati Reds in 1966, Robinson immediately won the Triple Crown and AL MVP with 49 home runs and 122 RBI.

Robinson was the fearsome presence in the middle of the lineup that the Orioles needed to take the next step as a franchise. Baltimore won the 1966 World Series with Robinson taking home the MVP. The O’s won another World Series in 1970 and suffered shocking losses at the hands of the New York Mets and Pittsburgh Pirates in 1969 and 1971. They very nearly won four World Series with Robinson.

For his Orioles tenure, Robinson was a .300/.401/.543 hitter with 179 of his 586 home runs. He was a two-time MVP with four seasons with an OPS over 1.000 and over 2,900 hits and 1,400 walks. Milt Pappas was the main return to the Reds, and he was a solid pitcher who won over 200 games in his MLB career. Pappas only pitched two years for the Reds before moving on to finish out his career with the Atlanta Braves and Chicago Cubs.

In our post last week breaking down each team’s best trade ever, we elected to go with the Jones-Tillman trade over the Robinson trade for the Orioles because of the impact the two All-Stars had on the franchise coming out of one the darkest stretches in team history. It’s rare that a team can get two All-Stars in a deadline deal, but the Orioles did and Jones and Tillman completely reversed the direction of the franchise. In terms of overall baseball impact, Robinson was a notch above both Jones and Tillman.