a Meatloaf Special's worth of these deals:
December 4, 1968: The Orioles trade John Mason and Curt Blefary to the Houston Astros for Mike Cuellar, Elijah Johnson, and Enzo Hernandez. We can cut to the chase here; Mason and Johnson never made the majors and the historically weak-hitting Hernandez was dealt to San Diego in the Pat Dobson swap before making his MLB debut, so this one comes down to the 1965 Rookie of the Year Blefary straight-up for Cuellar. Blefary, battling alcoholism, lasted four more seasons in the big leagues, only one of which was spent in Houston (.253/.347/.393, 109 OPS+, 1.6 bWAR, 12 HR, 67 RBI). The Cuban righty, meanwhile, lasted eight seasons in Baltimore, which was good enough for three American League pennants, one World Series title, one Cy Young Award, and a pair of All-Star appearances. His O's totals: 143 wins, 88 losses, a 3.18 ERA, 133 complete games, and a 109 ERA+. He accumulated a pitching bWAR (Baseball-Reference's Wins Above Replacement) of 17.4 in that span. So this exchange was a clear win for the Birds.
December 4, 1974: The Orioles trade Bill Kirkpatrick, Rich Coggins, and Dave McNally to the Montreal Expos for Mike Torrez and Ken Singleton. Again, Kirkpatrick was a career minor leaguer, so out he goes. Coggins, who'd seen his OPS plunge from .831 as a rookie to .618 in his sophomore season, lasted all of 13 games north of the border before being sold to the Yankees. His career lasted a total of 103 games in two post-Oriole seasons. McNally was entering his age 32 season with a dozen years' worth of major league mileage on his left arm. He added a scant 77.1 innings to his ledger with the Expos, allowing 88 hits and going 3-6 with a 5.24 ERA (-0.5 bWAR) before retiring and serving as a test case in the Players' Association fight for free agency. The 28-year-old Torrez was a 20-game winner for the only time in his career in 1975, putting up a 3.06 ERA (115 ERA+, 3.5 bWAR) despite a league-leading total of 133 walks. He was flipped to Oakland on the eve of the 1976 season in the Reggie Jackson blockbuster. The December '74 trade would be a mismatch even without the inclusion of Ken Singleton; throw him in, and it becomes a laugher. Singleton, also 28 at the time, served the O's for the final decade of his career. He was a three-time All-Star as an Oriole, with a pair of top-three MVP finishes. He gave the club a career triple-slash line of .284/.388/.445 and an OPS+ of 135. His cumulative bWAR in Baltimore was an even 30, which takes into account a dreadful last act in 1984 (-1.9 bWAR). If you like the counting stats, Kenny slugged 182 homers and drove in 766 in orange and black. Well done, guys.
December 4, 1988: The Orioles trade Eddie Murray to the Los Angeles Dodgers for Juan Bell, Brian Holton, and Ken Howell. Welp, this is the one that did not go as planned. Howell, who had been a mediocre reliever in L.A., was quickly moved to the Phillies with pitcher Gordon Dillard in exchange for Phil Bradley. That was fine, as Bradley was worth 3.5 bWAR in a season and a half in Charm City. Holton gave the Birds 174.1 forgettable innings of relief and spot starts in two seasons (7-10, 4.18 ERA, 91 ERA+, -0.5 bWAR). Juan Bell did not make anyone forget the name of Cal Ripken, with a putrid line of .172/.201/.249 in the 1991 season, his lone full year on the O's roster. From there it was off to Philly, Milwaukee, Montreal, Boston, and eventually Taiwan. Murray, entering his age 33 season in 1989, outlasted all of the players for whom he had been traded. He wasn't the star he'd been in Baltimore, but he did produce steadily through the 1996 season and had great individual efforts in 1990 (.330/.414/.520, 159 OPS+) and 1995 (.323/.375/.516, 129 OPS+). He reached the 3,000-hit and 500-homer milestones in the last few years of his run, the latter coming in his 1996 pennant race return to the Orioles. It's not so much that the O's were wrong to trade Eddie when they did. They just got a whole pile of nothing in exchange for him.
Don't be sad...'cause two out of three ain't bad...