Yankees Fleeced Orioles In 17-Man Trade

Yankees Fleeced Orioles In 17-Man Swap After 1954 Campaign

By Dan Schlossberg

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Special from the IBWAA. This article was printed in the IBWAA newsletter Here's the Pitch on February 27, 2026 and is used with permission.

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This year marks the 50th anniversary of an 10-man trade between the Yankees and Baltimore Orioles. But that wasn’t even the biggest deal between the two clubs.

On Nov. 17, 1954, the teams made a 17-man trade that involved eight “players to be named later” and took three weeks to complete.

The biggest trade in baseball history, it could never happen again in this era of complicated contracts containing full or limited no-trade clauses — not to mention nine figures in some cases.

The oversized swap started a month after the 1954 World Series when the Yankees sent Harry Byrd, Jim McDonald, Willy Miranda, Hal Smith, Gus Triandos, and Gene Woodling to Baltimore for Billy Hunter, Don Larsen, and Bob Turley.

On Dec. 1, New York moved Bill Miller, Kal Segrist, Don Leppert, and Theodore Del Guercio to the newly-minted O’s — who had just finished their first year in Maryland after transitioning from the St. Louis Browns — for Mike Blyzka, Darrell Johnson, Jim Fridley, and Dick Kryhoski.

Not all those players were household names, even among rabid fans, but some became legendary.

Larsen, who had gone 3-21 for the 1954 Orioles, went on to pitch the only perfect game in World Series history for the Yankees against the Brooklyn Dodgers two years later. Before he quit after 17 seasons, Larsen reached the World Series five times, four with the Yankees and one against them — for the 1962 San Francisco Giants.

Two years after Larsen’s 2-0 perfecto, New York won another world championship when Turley bested the World Champion Milwaukee Braves — and capped his year with a Cy Young Award. He was part of three other world champions while in Yankee pinstripes.

Woodling, an outfielder who went back and forth between the Yankees and Orioles so many times he should have bought a lifetime Amtrak ticket, became a productive player who lasted 17 seasons, retiring just before he reached 40.

And Triandos developed into an All-Star catcher who not only hit home runs but learned to handle Hoyt Wilhelm’s Hall of Fame knuckleball. In fact, Wilhelm — a reliever with amazing longevity — once pitched a no-hitter against the Yankees as a starter! Triandos, his catcher that day, Sept. 20, 1958, knocked in the only run of the game with a solo home run.

Both sides liked the enormous trade so much that they made another one. Completed just before free agency made such swaps impossible, the teams got together on trade deadline day — June 15, 1976 — and moved some memorable names.

The Yankees sent Rick Dempsey, Tippy Martinez, Rudy May, Scott McGregor, and Dave Pagan to Baltimore for Doyle Alexander, Ken Holtzman, Jimmy Freeman, Grant Jackson, and Elrod Hendricks.

That time, the O’s got A’s for execution on their report card: McGregor was the top starter on the 1983 Baltimore team that won the World Series, while Martinez was the closer and Dempsey was their catcher.

Trades within the same division are rare, but the second mega-swap involving Baltimore and the Bronx certainly qualifies.

When free agency hit with full force after that season, most future deals involved teams raiding each other’s players on the open market.

It was a sad day for lovers of great baseball trades — especially for Orioles fans still gloating over their acquisition of future Hall of Famer Frank Robinson from the Reds for Milt Pappas, Dick Simpson, and Jack Baldschun after the 1965 season (Robinson promptly won a Triple Crown and led the O’s to another world championship).

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HtP weekend editor Dan Schlossberg of Fair Lawn, NJ covers baseball for forbes.com, Memories & Dreams, USA TODAY Sports Weekly, Sports Collectors Digest, and a myriad of other outlets. He’s also the author of 43 baseball books.