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Ranking the top 5 trade deadline moves in Orioles history

The O's don't have a great track record with deadline deals, but through the years they've pulled off a few good ones.

Mitchell Layton/Getty Images

With the MLB trade deadline coming up in a matter of hours, it's looking like the O's probably won't be making any blockbuster moves. For a franchise that's had a good bit of historical success, the history for the Orioles in this particular category is pretty poor. The norm for Baltimore at the deadline has been dormancy, with a few impact-less trades scattered in.  But there are exceptions to every rule, and even the Orioles have pulled off some great deals in July. Here are my rankings for the top 5 deadline moves in franchise history.

5) 7/31/99: Orioles trade P Juan Guzman to the Reds for P Jacobo Sequea and P B.J. Ryan

At 46-56 on deadline day the '99 O's were clearly sellers, so they sent 32-year-old starter Juan Guzman to Cincy for two young pitchers. Guzman actually pitched very well for the Reds after the trade, posting a 3.03 ERA in 12 starts, but he left for Tampa Bay after the season and appeared in only one game in 2000 before eventually retiring. Meanwhile, Sequea never made the majors. The star of the trade turned out to be the young lefty Ryan. For four years Ryan was mainly a LOOGY for the Birds, but in 2004 he posted a 2.28 ERA in 87 innings as the setup man for Jorge Julio. Ryan took over the closer role in 2005 and had an All-Star campaign, with a 2.43 ERA and 36 saves. He then famously signed a massive contract with Toronto and was plagued by injury the rest of his career. He ended up accumulating about 8 WAR over 379 innings in 7 seasons for the Orioles.

4) 7/30/11: Orioles trade P Koji Uehara to Rangers for P Tommy Hunter and 1B Chris Davis

Koji was having a tremendous year for the O's with a sub-2 ERA, allowing Andy MacPhail to sell high to Texas as they made their push for a second straight World Series appearance. Tommy Hunter struggled as a starter but became an effective reliever near the end of 2012 and was similarly solid in '13 and '14. Meanwhile, Texas had one too many first basemen and decided Davis was the expendable one. All he did was set an Orioles record with 53 home runs in 2013 and post solid offensive seasons in 2012 and 2015 (so far). Both of these guys might be in different uniforms next year, but the O's still got a ton of value for a short reliever who was probably going to leave after the 2012 season anyway.

3) 6/28/00: Orioles trade SS Mike Bordick to the Mets for P Pat Gorman, P Leslie Brea, OF Mike Kinkade and IF/OF Melvin Mora

The slick-fielding Bordick had a career year at the plate in 2000, and the Mets had to send four players to Baltimore in order to rent Bordick for the end of his only All-Star campaign. Gorman never made the bigs, Brea only had a 9-inning cup of coffee, and Kinkade never lived up to his potential at the plate. Mora, though, became one of the better players in Orioles history. It took a few years, but Mora transformed himself from a light-hitting supersub to one of the best hitters in the league during his prime. He was an All-Star in 2003 while playing six different positions, and made a second All-Star Game in 2005 as a full-time third baseman. Somehow he didn't make the Midsummer Classic in 2004 despite finishing with a .340 average and leading the league with a .419 on-base percentage. Mora ended up playing ten years in Baltimore, accumulating over 1300 hits and 29 bWAR for the Orioles. Camden Chat named him the 15th best Oriole of all time last year. As if the deal wasn't one-sided enough, Bordick returned to Baltimore in free agency a few months later.

2) 7/29/88: Orioles trade P Mike Boddicker to Red Sox for OF Brady Anderson and P Curt Schilling

This could easily have been put in the #1 spot, as Boston paid a huge price for the veteran Boddicker. Brady played 14 seasons for the Orioles and finished his O's career with 1614 hits, 307 steals, and 34.7 bWAR, good enough to be named the 11th best Oriole of all time by Camden Chat. He also famously went bananas in 1996, setting a then-Orioles record with 50 home runs. Meanwhile, Schilling only became a six-time All-Star and one of the best postseason pitchers in the history of the game. Unfortunately he did all of that for other teams, because the O's followed one of the best trades in franchise history with the hands-down worst trade in franchise history a couple years later. The O's traded Schilling, Steve Finley, and Pete Harnisch to Houston for first baseman Glenn Davis, who never regained his All-Star form in a disappointing 3-year Oriole career. Boddicker, by the way, pitched well for the Sox after the trade. He ended up with a 3.49 ERA in 83 Boston starts over three seasons.

1) 6/15/76: Orioles trade P Doyle Alexander, P Jimmy Freeman, C Elrod Hendricks, P Ken Holtzman, and P Grant Jackson to Yankees for C Rick Dempsey, P Tippy Martinez, P Scott McGregor, P Rudy May and P Dave Pagan

Big trades were made less often back when the deadline was June 15th, but this was a blockbuster. Ten players changed sides in this one and the O's definitely got the better side of the deal. Alexander only made 19 starts for the Yankees, and hung around the majors until 1989 as a journeyman back-end starter. Freeman never pitched a major league inning after the trade and Holtzman had an ERA approaching five in two underwhelming seasons for New York. Jackson actually had a good 18-year career as a reliable middle reliever, but only pitched in 21 games for the Yankees. Hendricks was washed up by the time he made it to New York, and only made 68 Yankee plate appearances.

For the Orioles, May posted a decent 3.68 ERA over a season and a half in the Orioles' rotation. He signed with Montreal in 1978. Pagan only pitched in 20 games for the O's and sucked, but the Mariners took him anyway in the 1977 expansion draft.

Martinez, McGregor, and Dempsey were all key members of the successful Orioles teams in the 1970s and 1980s. Martinez pitched out of the O's bullpen for 11 years, and he was an All-Star during the 1983 World Championship season when he recorded a career-best 2.35 ERA in 103.1 innings. McGregor played his entire 13-year career in Baltimore and finished with 138 wins, a 3.99 ERA, and 20.2 bWAR. He won 20 games in 1980, was an All-Star in 1981, and had a 1.06 ERA over 2 starts in the 1983 World Series. Dempsey was one of the most beloved Orioles ever and played 12 of his 24 seasons in Baltimore. He was an unspectacular but solid hitter for a catcher, and he was named the 1983 World Series MVP after raking his way to a 1.390 OPS in a 4-1 series win. He's still a big part of the O's organization to this day. Dempsey ranked #20 on our top 40 list, and McGregor came in at #23.

Which of these deals do you think was the best in Orioles history? Is there one I'm forgetting? Let me know below.