The Tool Desk
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Babe Ruth sold to the Yankees (1919)
Boston sold Babe Ruth’s contract to New York after the 1919 season; it was not a player-for-player swap. Ruth had become a major power hitter, and the Yankees acquired a star whose impact would extend far beyond the immediate transaction. MLB describes the deal as one that changed baseball. MLB’s anniversary account notes that Ruth retired with 714 home runs.
The shock was apparent at the time. Yankees pitcher Bob Shawkey was quoted saying, “Gee, I’m glad that guy’s not going to hit against me anymore.” The sale became a defining moment in the rivalry and identity of the two clubs, and a lasting reference point whenever baseball’s biggest power hitters are discussed.
The transaction also survives in the historical record: the Hall of Fame’s librarian James Gates called the 1919 promissory note for Ruth’s sale “a critical piece of baseball history.” The Hall of Fame retrospective recounts the sale and its contemporary reception.
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Lou Brock to the Cardinals (1964)
In a six-player transaction, the Chicago Cubs sent Lou Brock to the St. Louis Cardinals, with pitcher Ernie Broglio going to Chicago as the central return. At the time, the Cubs were seeking pitching; the Cardinals gained an outfielder who would become central to their success. The Hall of Fame’s account calls the trade infamous in hindsight.
Brock went on to join the 3,000-hit club and become one of baseball’s greatest base-stealers. He finished with a then-record 938 stolen bases. Broglio did not deliver the value Chicago hoped for, making the deal a durable example of how a trade’s reputation can change as careers unfold. The National Baseball Hall of Fame and Museum’s account details the transaction and Brock’s legacy.
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Tom Seaver to the Reds (1977)
The June 15, 1977 trade sent Mets ace Tom Seaver to Cincinnati. The Reds sent pitcher Pat Zachry, outfielder Steve Henderson, infielder Doug Flynn and outfielder Dan Norman to New York. The deal became known as the “Midnight Massacre,” a label that captured the anger of Mets fans at losing a franchise-defining pitcher.
Seaver was an established star, while New York received a package intended to help rebuild. The trade remains memorable not simply because a great player changed teams, but because it came amid organizational turmoil and helped deepen the disconnect between the Mets and their supporters. ESPN’s historical list records the date and players in the return. ESPN’s historical blockbuster list is a secondary account.
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Rickey Henderson’s trade history
Rickey Henderson moved between clubs several times, so it is misleading to treat his career as one single famous trade. MLB’s retrospective focuses on his trade history and the challenge teams faced in fully valuing his talents. Former Oakland general manager Sandy Alderson recalled, “Probably in 1985, we didn’t have a full appreciation of all his talents.”
That hindsight is part of what makes Henderson’s movement memorable: he was not merely a fast leadoff hitter, but a singular combination of on-base skill, speed and disruptive baserunning. The available retrospective discusses multiple deals rather than establishing one definitive transaction as the standout. MLB’s Henderson trade retrospective provides the context.
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