At times, it can cause otherwise levelheaded organizations to do something crazy. Like trade away Jeff Bagwell for Larry Anderson. Or give up Grady Sizemore, Cliff Lee and Brandon Phillips for Bartolo Colon.
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The Orioles have never had any Bagwell-for-Anderson trades. They have made their share of regrettable moves (wherefore art thou, Curt Schilling and Steve Finley?), but they've never really given up any significant piece at the deadline, at least not without getting something of value in return.
With the Orioles considering adding a corner infield bat or starting pitcher, The Baltimore Sun has compiled a list of the O's best deals at the deadline, as well as those that had more mixed results.
The only criterion is that the deal must have been executed within a week of the trade deadline. Also note: the MLB has maintained the July 31 deadline since 1986, but before that year, the deadline was June 15.
I've broken down the trades into three categories. The Good, The Less Good and The Harold Baines, named after the player of the same name who was traded to and from Baltimore two times each. When you're in that many deals, you deserve your own category.
July 29, 1988: The Orioles acquired Curt Schilling and Brady Anderson from the Red Sox for Mike Boddicker.
The Orioles never reaped the benefits of their best deadline deal. Just three years later, they traded Schilling along with Steve Finley and Pete Harnisch to Houston for Glenn Davis. Still, the 1988 deal was a gem. Schilling is a potential Hall of Famer and Anderson hit 50 home runs for the O's in 1996. Boddicker pitched two more good years and one very good year, but the second half of his career isn't close to matching Schilling's resume.
June 15, 1970: The Orioles acquired Moe Drabowsky from the Royals for Bobby Floyd.
This trade makes the list because it gave the Orioles the final piece for a World Series-winning team. The Royals received a good player in Floyd, but Drabowsky recorded three saves in the 1970 World Series to help lead Baltimore to a championship.
July 30, 2011: The Orioles traded Koji Uehara and cash to the Rangers for Chris Davis and Tommy Hunter.
The Orioles addressed two needs with this deal. Even though Hunter has been disappointing, Davis' power gives the lineup some pop. And Uehara, who hasn't pitched in more than a month with a lat injury, is not missed in a bullpen that has been the team's bright spot.
July 28, 1995: The Orioles acquired Bobby Bonilla and Jimmy Williams from the Mets for Damon Buford and Alex Ochoa.
Bonilla was a .300 hitter in a year and a half with the Orioles, and his addition helped the Orioles reach the ALCS in 1996.
The Less Good
July 31, 2000: The Orioles acquired Trent Hubbard, Fernando Lunar and Luis Rivera to the Braves for B.J. Surhoff and Gabe Molina.
This deal is more sad than anything else. None of the players involved in the trade made any major impacts after the deal, but Orioles fans will remember B.J. Surhoff crying after learning he would no longer be an Oriole.