Five winners ...
December 1965: Acquired OF Frank Robinson from Reds for P Milt Pappas, P Jack Baldschun and OF Dick Simpson. Comment: Pappas was a solid starter, but what a small price to pay for a Hall of Famer, a Triple Crown, four pennants and two world championships. June 1976: Acquired P Scott McGregor, P Tippy Martinez, P Rudy May, P Dave Pagan and C Rick Dempsey from Yankees for P Ken Holtzman, P Doyle Alexander, P Grant Jackson, P Jimmy Freeman and C Elrod Hendricks. Comment: Deadline deal by GM Hank Peters did a lot more than dump a couple of pending free agents. It helped set up the glory days of the late '70s and early '80s.
December 1974: Acquired OF Ken Singleton and P Mike Torrez from Expos for OF Rich Coggins and P Dave McNally. Comment: The Orioles got 10 productive years from Singleton and a 20-win season from Torrez. McNally was out of the majors by 1975, Coggins by 1976. December 1968: Acquired P Mike Cuellar, SS Enzo Hernandez and IF Elijah Johnson from Astros for OF Curt Blefary and minor leaguer John Mason. Comment: Cuellar helped build the Orioles' tradition of great pitching, sharing the 1969 AL Cy Young Award and posting four 20-win seasons. His best years were with the Orioles - and so were Blefary's. July 1988: Acquired OF Brady Anderson and P Curt Schilling from Red Sox for P Mike Boddicker. Comment: Anderson gave the Orioles a leadoff hitter with some pop for a decade. Boddicker retired in 1993. Now, if the Orioles had just hung on to that Schilling guy ... ... and five losers
January 1991: Acquired 1B Glenn Davis from Astros for P Curt Schilling, P Pete Harnisch and OF Steve Finley. Comment: Davis' pain in the neck continues to hurt the Orioles. The expensive, often-injured slugger was released in 1993. Schilling and Finley are still going strong. Harnisch won 111 games in 14 years. Ouch. December 1972: Acquired C Earl Williams and IF Taylor Duncan from Braves for P Pat Dobson, P Roric Harrison, 2B Davey Johnson and C Johnny Oates. Comment: Williams clashed with Earl Weaver and lost the power stroke he had in Atlanta. Johnson suddenly found one and hit 43 homers in his first year as a Brave. December 1988: Acquired P Brian Holton, P Ken Howell and IF Juan Bell from Dodgers for 1B Eddie Murray. Comment: Trading a Hall of Famer for three journeymen was bad enough. What's worse, it left a void at first base that eventually led the Orioles to trade for ... Glenn Davis. December 1971: Acquired P Doyle Alexander, P Bob O'Brien, C Sergio Robles and 1B Royle Stillman from Dodgers for OF Frank Robinson and P Pete Richert. Comment: The club was making room for a young Don Baylor, but Robinson, 36, had a few good years left, and his leadership was missed. The Orioles' run of pennants ended with his departure. Alexander's Orioles years weren't his best. July 1992: Acquired minor league OF Kyle Washington from Indians for P Jose Mesa. Comment: A dozen years later, Mesa is still saving games while the Orioles have gone though the likes of Doug Jones and Ryan Kohlmeier in the closer's role. Washington never made it to the majors.