10 biggest trades in Orioles history

December 1st, 2021

Since the club moved to Baltimore, trades have played an important role in shaping the history of the Orioles. Some have altered the future of the franchise, while others amounted to little. Some hit big, some hurt.

Either way, the years have left a trail of memorable transactions. Here is a look at the 10 most memorable trades in franchise history.

1. A Hall-worthy coup

Orioles got from Reds: OF Frank Robinson
Orioles gave up: RHP Jack Baldschun, RHP Milt Pappas, OF Dick Simpson
Date: Dec. 9, 1965

This was one of the more lopsided trades in baseball history, and certainly in the history of the O's. Pappas was a three-time All-Star at the time, and he pitched eight more seasons after the trade. But Robinson only accelerated his Hall of Fame track once in Baltimore, winning the American League Triple Crown and the AL MVP Award in his first season and earning six more All-Star appearances in all. He went into Cooperstown wearing an Orioles cap.

2. Planting seeds for success

Orioles got from Yankees: C Rick Dempsey, LHP Tippy Martinez, LHP Rudy May, LHP Scott McGregor, RHP Dave Pagan
Orioles gave up: RHP Doyle Alexander, LHP Jimmy Freeman, C Elrod Hendricks, LHP Ken Holtzman, LHP Grant Jackson
Date: June 15, 1976

In what is amazingly just their second-biggest trade made with the Yankees, the Orioles acquired three key cogs for their 1983 championship team in Dempsey, McGregor and Martinez. The trio also helped the O's to an AL pennant in 1979.

3. Calling AJ & Co.

Orioles got from Mariners: OF , LHP George Sherrill, RHP Chris Tillman, RHP Kam Mickolio, LHP Tony Butler
Orioles gave up: LHP Erik Bedard
Date: Feb. 8, 2008

Sensing an opportunity to fuel his planned rebuild, team president Andy MacPhail traded Bedard to Seattle after the 2007 season, when he finished fifth in the AL Cy Young Award voting. The oft-injured lefty would make only 46 starts for the Mariners, while the Orioles' return set them up for more than a decade.

The package centered on Jones, who became one of the most popular -- and productive -- players in franchise history. Tillman grew into an All-Star and rotation fixture. Sherrill made an All-Star appearance as well before he was flipped for Josh Bell, who, despite never making much impact at the big league level, was a top prospect at the time.

4. Cuell-er's market

Orioles got from Astros: LHP Mike Cuellar, SS Enzo Hernandez, INF Tom Johnson
Orioles gave up: OF/C Curt Blefary, INF John Mason
Date: Dec. 4, 1968

The 1965 AL Rookie of the Year Award winner, Blefary had regressed into a below-average player by 1968, at which point the Orioles shipped him to Houston. The deal turned out to be a heist. Cuellar posted six straight seasons with at least 18 wins and a sub 3.50 ERA, and he won a share of the AL Cy Young Award in 1969.

5. Whoops

Orioles got from Astros: 1B Glenn Davis
Orioles gave up: RHP Pete Harnisch, RHP Curt Schilling, OF Steve Finley
Date: Jan. 10, 1991

The biggest flop on this list, the O's parted ways with three soon-to-be-impact players for Davis, who played like a shell of his former self over three seasons in Baltimore. Schilling, Harnisch and Finley went on to combine to make nine All-Star appearances, with Schilling building a borderline Hall of Fame career.

6. Sending for Singleton

Orioles got from Expos: OF Ken Singleton, RHP Mike Torrez
Orioles gave up: LHP Dave McNally, OF Rich Coggins, RHP Bill Kirkpatrick
Date: Dec. 4, 1974

McNally was a three-time All-Star and four-time 20-game winner in Baltimore, but he was 32 years old by the time the Orioles sent him to Montreal. McNally would retire after one more campaign, while Singleton hit .284/.388/.445 with 182 home runs across 10 seasons with the O's and made three All-Star teams. He was also a part of their 1983 championship team and the AL MVP runner-up in 1979.

7. Manny time

Orioles got from Dodgers: OF Yusniel Diaz, RHP Dean Kremer, RHP Zach Pop, INF , INF Rylan Bannon
Orioles gave up: SS/3B Manny Machado
Date: July 18, 2018

It'll be years before the Orioles' return can be properly assessed, but this deal earns its spot on this list on the basis of whom Baltimore gave up. With Machado approaching free agency and the Orioles preparing for a rebuild, they finally dealt their homegrown star after rumors teased at their intentions for years. Machado helped the Dodgers toward a World Series appearance before hitting the open market. For the O's, sending Machado out was just the start of a midsummer selloff that spared few veterans.

8. Brady for Boddicker

Orioles got from Red Sox: OF Brady Anderson, Schilling
Orioles gave up: RHP Mike Boddicker
Date: July 29, 1988

Outside of his masterful 1984 campaign, Boddicker was a useful, if merely average, starter for much of his nine years in Baltimore. Swapping him for the then 24-year-old Anderson showed foresight. Anderson, a former 10th-round pick, became a mainstay in center field, hit a franchise-record 50 homers in 1996 and remains employed by the club in a front-office capacity.

This deal only ranks this low because the O's eventually traded Schilling, well before he blossomed into a star.

9. Crush comes to town

Orioles got from Rangers: 1B Chris Davis, RHP Tommy Hunter
Orioles gave up: RHP Koji Uehara
Date: July 30, 2011

Perception of the trade that brought Davis to Baltimore has changed over time. Through one lens, swapping a middle reliever for a two-time home run champion looks like a win. Today, though, Davis' precipitous decline and massive contract make him one of baseball's most infamous albatrosses.

10. The most mega deal of them all

Orioles got from Yankees: C Gus Triandos, OF Gene Woodling, SS Willy Miranda, C Hal Smith, RHP Jim McDonald, RHP Harry Byrd, LHP Bill Miller, INF Kal Segrist, 2B Don Leppert, OF Theodore Del Guercio
Orioles gave up: RHP Don Larsen, RHP Bob Turley, INF Billy Hunter, RHP Mike Blyzka, C Darrell Johnson, OF Jim Fridley, 1B Dick Kryhoski
Date: Nov. 17, 1954

After 1954, the Yankees were desperate to leapfrog back to the top of the AL following a rare second-place finish. The Orioles were just desperate -- they'd finished 57 games out that year, their first in Baltimore after moving from St. Louis.

It is with this as a backdrop that the two clubs pulled off a deal that was unprecedented at the time, and hasn't been replicated since. The 17-player swap still ranks as the biggest trade in MLB history in terms of number of players involved.