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Yankees Trade Partner History: Baltimore Orioles

The Yankees and Orioles have to their names the largest trade in baseball history.

St. Louis Cardinals v Baltimore Orioles Photo by Mitchell Layton/Getty Images

As two of the oldest franchises in the American League, the Yankees and Orioles (née Browns) have a long history of making deals with each other, and even though it is fairly rare for two teams within the same division to make deals with each other, the two sides have come together fairly frequently over the past few years.

That said, in many ways, the two sides are known just as much for the deals they were unable to complete (such as Manny Machado) as they are for the deals that they were able to push past the finish line.

Best Trade

November 17, 1954: The Yankees traded players to be named later, Harry Byrd, Jim McDonald, Willy Miranda, Hal Smith, Gus Triandos, and Gene Woodling to the Orioles for players to be named later, Billy Hunter, Don Larsen, and Bob Turley. The Yankees sent Bill Miller (December 1, 1954), Kal Segrist (December 1, 1954), Don Leppert (December 1, 1954), and Theodore Del Guercio (December 1, 1954) to the Orioles to complete the trade. The Orioles sent Mike Blyzka (December 1, 1954), Darrell Johnson (December 1, 1954), Jim Fridley (December 1, 1954), and Dick Kryhoski (December 1, 1954) to the Yankees to complete the trade.

From sheer size alone, this trade belongs in a “Weirdest Trade” category all its own — a total of 17 players flipped sides in this deal, including eight who were classified as “players to be named later.” It is the largest deal in baseball history, and trails only the Herschel Walker deal in sports history (that trade saw 18 players and picks involved).

But what turns this from the weirdest trade to the best trade are the players involved. In desperate need to reinvent their pitching staff to extend their championship window, the Yankees sent a package headlined by Gus Triandos and Gene Woodling to the Orioles for Bob Turley, Don Larsen, and Billy Hunter. Turley and Larsen would go on to fill critical roles in the Yankees rotation for the next half a decade, with Turley being a part of four championship teams and Larsen partnering with Yogi Berra to achieve baseball immortality.

Worst Trade

February 21, 2017: The Yankees trade Richard Bleier to the Orioles for player to be named or cash.

On the surface, trading away a Quadruple-A relief pitcher for a player to be named later is hardly something worth complaining about. Everything surrounding this deal, however, represents one of the worst series of moves the Yankees have made. First, the team designates Bleier, who had looked pretty good in limited action in 2016, for assignment to make room on the 40-man roster for Chris Carter, the player who led the league in home runs in 2016 but had remained unsigned to that point because he did nothing else well. They then flipped Bleier to a division rival, where over the next two seasons he would post a 1.97 ERA in 88 innings, becoming one of Baltimore’s most important relief arms.

While the fallacy of the predetermined outcome — Michael Kay’s favorite phrase — forbids us from saying that Bleier would have performed just as well in pinstripes, the 2017 Yankees did not exactly boast a strong bullpen heading into the season. It was only after the blockbuster deal that brought David Robertson and Tommy Kahnle to the Bronx that the team assembled the “super bullpen” that allowed them to win the 2017 Wild Card Game despite the fact that Luis Severino recorded only one out.

Most Overlooked Trade

July 24, 2018: The Orioles trade Zack Britton to the Yankees for Cody Carroll, Josh Rogers, and Dillon Tate.

Now, I know what you’re thinking. “This was one of the Yankees’ biggest deadline moves of the Baby Bombers era, how could it possibly be considered overlooked?” What makes this deal overlooked, in my mind, is just how underrated Zack Britton’s time in pinstripes was and how the circumstances surrounding his arrival and his late-career injury-filled struggles color popular perception of the lefty reliever. When he came over, rumors connecting Manny Machado to the Yankees had been circulating, making Britton seem a little bit of a letdown. His final two seasons, meanwhile, saw him post a 6.16 ERA in 19 innings across 2021 and 2022 at the worst time possible. He never really made it back from Tommy John surgery.

Over his first two and a half seasons with the Yankees, however, Britton was electric, posting a 2.14 ERA and accruing 1.5 fWAR in 105 innings. He filled a number of roles — setup man, fireman, lefty specialist, and (when Aroldis Chapman was injured or in a funk) closer.

Weirdest Trade

November 12, 2006: The Yankees trade Jaret Wright and cash to the Orioles for Chris Britton.

Years before they acquired Zack Britton in a trade from the Orioles, the Yankees acquired a pitcher named Chris Britton from Baltimore. Are the two pitchers related? Not as far as I can tell.

Chris did not do nearly as well in pinstripes as his similarly-named counterpart, posting a 4.54 ERA in 35 innings across the 2007 and 2008 seasons. Were it not for Zack’s success in the Bronx, he would be just another reliever picked up in a minor salary-dump deal who made a cameo in the big leagues before moving on.

Other Trades of Note

September 10, 1933. The St. Louis Browns purchase Jim Weaver from the Yankees.
May 15, 1934. The St. Louis Browns return Jim Weaver to the Yankees following previous purchase.

The runner-up for “weirdest trade,” apparently the St. Louis Browns had a receipt for Jim Weaver. He made just five starts for the Browns, posting a disastrous 6.41 ERA. The Yankees didn’t want him back, though; they immediately put him on waivers, where he was picked up by the Chicago Cubs.

June 15, 1976: The Yankees trade Rick Dempsey, Tippy Martinez, Rudy May, Scott McGregor, and Dave Pagan to the Orioles for Doyle Alexander, Jimmy Freeman, Elrod Hendricks, Ken Holtzman, and Grant Jackson.

Another megadeal between the Yankees and Orioles, this one wasn’t quite the sure-fire win for the Bombers. As part of this ten-player deal, the Yankees surrendered Rick Dempsey, Tippy Martinez, and Scott McGregor — the catcher, closer, and No. 1 starter on the O’s 1983 World Series championship team.



Ghiroli, Brittany. “O’s acquire lefty Bleier from Yanks for PTBN.” February 21, 2017.

“The NFL’s largest trade.” Pro Football Hall of Fame. October 14, 2009.

Trezza, Joe. “10 biggest trades in Orioles history.” December 1, 2021.

Previously in the Trade Partner History series

Los Angeles Dodgers
Full list to date