Dec. 9, 1965
Deal -- Pitchers Milt Pappas and Jack Baldschun and outfielder Dick Simpson to Cincinnati Reds for outfielder Frank Robinson.
Details -- The Reds considered Robinson an "old 30," but he won the Triple Crown in his first season and was named Most Valuable Player of the American League and the World Series, in which the Orioles swept the Los Angeles Dodgers to win their first title. He led the Orioles to four AL pennants in six seasons. Meanwhile, Pappas went 30-29 in 2 1/2 seasons for the Reds.
Dec. 4, 1968
Deal -- Outfielder/first baseman/catcher Curt Blefary and outfielder John Mason to Houston Astros for pitcher Mike Cuellar and infielders Elijah Johnson and Enzo Hernandez.
Details -- Cuellar's best season in Houston was 1967, when he was 16-11. His record fell to 8-11 the next year, but he posted three straight 20-win seasons after the trade and added a fourth in 1974. Cuellar shared the Cy Young Award in 1969 and was a four-time All-Star. Blefary batted .253 in his only season with the Astros and finished as a .237 career hitter in eight major league seasons. He hit 22, 23 and 22 homers in his first three seasons with the Orioles but didn't exceed 12 after the trade.
Nov. 30, 1972
Deal -- Second baseman Davey Johnson, catcher Johnny Oates and pitchers Pat Dobson and Roric Harrison to Atlanta Braves for catcher Earl Williams and infielder Taylor Duncan.
Details -- Johnson never hit more than 18 home runs with the Orioles, but he totaled 43 with the Braves in 1973. That alone was reason enough to void this trade. Williams clashed with manager Earl Weaver and just about everyone else in the organization. He was named National League Rookie of the Year in 1971 after hitting a career-high 33 homers, but he lasted only two seasons with the Orioles before returning to the Braves.
April 2, 1976
Deal -- Outfielder Don Baylor and pitchers Mike Torrez and Paul Mitchell to Oakland Athletics for outfielder Reggie Jackson and pitcher Ken Holtzman.
Details -- Jackson spent one season in Baltimore before signing a five-year, $2.96 million contract with the New York Yankees. He hit 27 homers and drove in 91 runs after reporting late to the club. Holtzman was 5-4 in a half season with the Orioles. Baylor was named AL MVP with the California Angels in 1979 and rates as one of the best designated hitters in baseball history. Torrez went 185-160 in 18 seasons.
June 15, 1976
Deal -- Pitchers Ken Holtzman, Doyle Alexander, Grant Jackson and Jimmy Freeman and catcher Elrod Hendricks to Yankees for pitchers Scott McGregor, Tippy Martinez, Rudy May and Dave Pagan and catcher Rick Dempsey.
Details -- The Yankees played in three straight World Series after this deal, winning two, but the Orioles were the true benefactors based on the production of the players involved. McGregor went 138-108 in parts of 13 seasons in the majors, all with the Orioles, and recorded the final out in the 1983 World Series, when Dempsey was named MVP. Martinez recorded 105 saves as the Orioles' closer.
July 29, 1988
Deal -- Pitcher Mike Boddicker to Boston Red Sox for pitcher Curt Schilling and outfielder Brady Anderson.
Details -- Their season already shot after an 0-21 start, the Orioles traded Boddicker for two prospects. Boddicker went 7-3 down the stretch for the Red Sox, helping them win the AL East, and was 15-11 in 1989 and 17-8 with a 3.36 ERA in 1990. But the Orioles didn't fare too badly. Anderson evolved into one of the game's best leadoff hitters and hit 50 home runs in 1996. Schilling had maturation issues, and his best years came after the Glenn Davis trade.
Dec. 4, 1988
Deal -- First baseman Eddie Murray to Los Angeles Dodgers for shortstop Juan Bell and pitchers Ken Howell and Brian Holton.
Details -- Murray drove in 88, 95 and 96 runs in three seasons with his hometown Dodgers and eventually went into the Hall of Fame as an Oriole. Bell and Holton had undistinguished careers, and Howell never pitched for the Orioles, who shipped him to the Philadelphia Phillies four days later for outfielder Phil Bradley.
Jan. 10, 1991
Deal -- Pitchers Pete Harnisch and Curt Schilling and outfielder Steve Finley to Astros for first baseman Glenn Davis.
Details -- Davis averaged 28 homers at the Astrodome in six seasons but hit only 10 in 1991 while dealing with a mysterious nerve condition that caused the muscles behind his right shoulder to atrophy. He hit 13 homers the next season and was released in 1993 after 30 games. Harnisch won 95 games after leaving Baltimore, though his career was derailed because he suffered from depression that he blamed on tobacco use. Schilling has won 216 games and three World Series in 20 seasons. Finley hit 30 or more homers four times and played for parts of 17 seasons after the trade, twice making the All-Star team.
Dec. 12, 2007
Deal -- Shortstop Miguel Tejada to Astros for outfielder Luke Scott, pitchers Troy Patton, Matt Albers and Dennis Sarfate, and third baseman Mike Costanzo.
Details -- It will take a few years to determine a winner, but Tejada's declining power and range, and the perception that he would be happier elsewhere, made dealing him a priority for the Orioles. Scott could be the regular left fielder in Baltimore, and Patton and Albers were rated among the Astros' top prospects and will compete for spots in the rotation. Sarfate is a hard-throwing late-innings reliever who is out of minor league options and could work in a setup role with the Orioles. Costanzo has impressive power but needs to cut down on the strikeouts and errors.