The 5 best Orioles trades of the last 25 years

These 5 trades have been clear wins for the Orioles
Boston Red Sox v Baltimore Orioles
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The Baltimore Orioles' trade history is a bit of a mixed bag. Sure, they struck gold on December 9, 1965 when they landed future AL MVP Frank Robinson in a trade with the Reds. But 25 years later, they shortsightedly traded future All-Star Curt Schilling and solid Major Leaguers Steve Finley and Pete Harnish for an aging and injury-prone Glenn Davis.

There are important trades that flew under the radar (i.e. the Orioles trading Juan Guzman for future All-Star closer BJ Ryan), trades you have probably forgotten about (remember when the Orioles traded Xavier Avery for Michael Morse?), and trades we would just as soon forget (Jake Arrieta for Scott Feldman).

Now that the Texas Rangers have won the World Series, and trade season and free agency creeps closer, we will re-live some of the best trades the Orioles have made over the last 25 years to throw some positivity on the start of the offseason. Fair warning: over the last 25 years, the Orioles only had 6 winning seasons. So winning trades were few and far between.

(5) Orioles acquire Melvin Mora, Leslie Brea, Mike Kinkade, and Pat Gorman from the Mets for Mike Bordick

Melvin Mora, Ryan Doumit
Baltimore Orioles v Pittsburgh Pirates / George Gojkovich/GettyImages

Under then-GM Frank Wren, the 2000 Orioles executed a bevy of trades ahead of the July 31, 2000 deadline, dealing away veterans Charles Johnson, Mike Timlin, B.J. Surhoff, and Will Clark. None of these trades during the sell-off of 2000 netted a significant return, except for a deal sending SS Mike Bordick to the Mets for Melvin Mora, Leslie Brea, Mike Kinkade, and Pat Gorman. The Mets, who played in the Subway Series World Series in 2000 against the Yankees, acquired Bordick after longtime glove-first shortstop Rey Ordonez went down to injury midway through the season.

Although not initially contemplated as the major prize of this trade (that was Leslie Brea), Mora went on to have 9.5 productive seasons in Baltimore. The versatile Mora primarily played third for the Orioles, but also saw time at shortstop, second base, centerfield, and left field for the O's. His best season came in 2004, when he hit an eye-popping .340 with 27 home runs, 88 RBIs, and a .981 OPS.

A two time All-Star with the Orioles, Mora also earned a Silver Slugger award in his time in Baltimore. Outside of baseball, Mora was a pillar in the community and experienced the birth of quintuplets while he was in Baltimore. While none of the other players acquired from New York for Bordick contributed to the Orioles, Mora himself made the trade a big win for Baltimore.

For his part, Bordick played in the World Series with the Mets before returning to the Orioles in the 2001 offseason as a free agent.

(4) Orioles acquire Kyle Bradish, Kyle Brnovich, Zach Peek, and Isaac Matson from the Angels for Dylan Bundy

Kyle Bradish, Adley Rutschman
Division Series - Texas Rangers v Baltimore Orioles - Game One / Greg Fiume/GettyImages

During the early seasons of the Orioles' rebuild under Mike Elias, they may as well have had a sign: "Anything and everything must go." Fortunately for Orioles fans, one of those players that had to go was Dylan Bundy who, despite being a high draft pick with an advanced pedigree out of high school, never put it together for the Orioles. In December 2019, the Orioles traded Bundy to the Angels for four pitching prospects: Kyle Bradish, Isaac Matson, Zach Peek, and Kyle Brnovich.

While the latter three have yet to make an impact with the Orioles, Bradish just completed an outstanding 2023 season, that saw him register a 12-7 record, 2.83 ERA, 168 strikeouts, and 1.04 WHIP. Bradish's ERA and WHIP were good enough for fourth in the junior circuit, and good enough to earn Bradish the nod as Baltimore's Game 1 starter in the ALDS.

While Bradish's postseason debut did not turn out great, there is no denying that Bradish emerged as the ace of the 101-win Orioles team. While Bradish has only had one terrific season, the Orioles are expecting big things from him and control the right-hander's rights through the 2028 season.

On the flipside, Dylan Bundy is no longer in the Major Leagues, and was ejected from a minor-league game for using a sticky substance this year. While some might argue it is too early to declare this one of the Orioles' best trades in recent memory, Bradish has the potential to be the ace of an annual playoff juggernaut for at least the next half-decade. The Angels' FanSided page has recognized as much, tabbing Bradish as the "one former Angels prospect who got away." This trade is already a big win for the Orioles, and it will likely only get better.

(3) Orioles acquire JJ Hardy and Brendan Harris from Minnesota for Jim Hoey and Brett Jacobson

Tampa Bay Rays v Baltimore Orioles
Tampa Bay Rays v Baltimore Orioles / G Fiume/GettyImages

The Orioles acquired shortstop JJ Hardy during the 2010-11 offseason as part of an overhaul to the entire offense. Along with Hardy, the Orioles acquired slugger Mark Reynolds from Arizona and signed veterans Vladimir Guerrero and Derrek Lee to one-year contracts. While Hardy was the least heralded of the group, he wound up making the greatest contribution to the Orioles.

Over seven solid seasons in Baltimore, Hardy won three gold gloves and one Silver Slugger and appeared in one All-Star game. He was the starting shortstop for the Orioles' 2012, 2014, and 2016 playoff teams and is known for scoring the go-ahead run in Game 2 of the ALDS on Delmon Young's bases-clearing double against Detroit. Hardy's playoff prowess also included the game-winning double in Game 4 of the 2012 ALDS at Yankee Stadium in the top of the 14th.

In his first three seasons in Baltimore, Hardy averaged over 25 home runs a season, and while his power wore off towards the end of his career, his steady leadership did not. From 2011 to 2014, Hardy was worth 4.0, 3.0, 3.7, and 3.4 WAR respectively. Not surprisingly, Hardy was elected into the Baltimore Orioles Hall of Fame in August 2021.

Hoey and Jacobson were two right-handed middle relievers whose Major League careers were short-lived. Minnesota would likely prefer to call a mulligan on this trade.

(2) Orioles acquire Chris Davis and Tommy Hunter from Texas for Koji Uehara

Chris Davis
Seattle Mariners v Baltimore Orioles / Mitchell Layton/GettyImages

The story of Chris Davis with the Baltimore Orioles is a two-act play. Before inking a 7 year, $161M contract with the Orioles, Davis was a Baltimore folk hero. Gargantuan home run blasts, a fan favorite, and along with Adam Jones, the offensive star of the Orioles' first winning season in 14 years. Act 2 of the play takes us from folk hero to Greek tragedy, as Davis suddenly morphed into one of the worst players in Major League baseball from 2017-2020, with a price tag so inflated that no team would even try to acquire him as a reclamation project.

Ding the summer of 2011, Orioles general manager Andy MacPhail traded reliever Koji Uehara to the Texas Rangers in exchange for Davis and right-hander Tommy Hunter. At this point in his career, Davis had shown flashes of power in Texas, but was unable to put together a full season.

Davis hit the ground running once he came to Baltimore. In 2012, Davis mashed a then-career high 33 home runs to go along with an .827 OPS and was a key cog in the Orioles first playoff run since 1997. He was even better in 2013, starting his first All-Star game, slugging 53 home runs, and mashing to the tune of a 1.004 OPS.

Davis put together three more solid seasons from 2014-2016 and ranks sixth all time in home runs for the Orioles with 253. While the final act of his career was one to forget, the production the Orioles acquired for a solid but replaceable relief pitcher was remarkable.

The other player acquired in the deal, Tommy Hunter, enjoyed parts of six successful seasons with the Orioles, eventually settling in as a key late-inning reliever during the team's mid 2010's playoff runs. In 2013, Hunter appeared in 68 games, going 6-5 with a 2.81 ERA, and followed that up with a 2.97 ERA in 60 games in 2014.

Hunter has enjoyed a solid Major League career, pitching as recently as 2023 out of the New York Mets bullpen. His inclusion in the deal with Davis made this trade an even bigger steal for the O's.

Uehara pitched well out of the Rangers bullpen in 2011 and 2012 before finishing his career with the Red Sox and Cubs.

(1) Orioles acquire Adam Jones, Chris Tillman, George Sherrill, Tony Butler and Kam Mickolio from Seattle for Erik Bedard

Adam Jones
Houston Astros v Baltimore Orioles / G Fiume/GettyImages

After the Orioles suffered their tenth straight losing season in 2007, Orioles GM and Vice President of Baseball Operations Andy McPhail realized the team needed a change. In December, he traded Miguel Tejada to the Astros for a package that included outfielder Luke Scott and lefty Troy Patton.

In February, McPhail made an even bigger splash, dealing the talented but mercurial Erik Bedard to the Mariners for a package of 5 players: outfielder Adam Jones, relief pitcher George Sherrill, and pitching prospects Chris Tillman, Tony Butler, and Kam Mickolio.

The Orioles immediately tabbed Jones their centerfielder of the future and enjoyed an exciting and successful 11-year run with Jones. One of the most popular and beloved players in recent memory, Jones hit 263 home runs as an Oriole, played in five All-Star games, won four Gold Gloves and one Silver Slugger, and even finished 6th in American League MVP voting in 2012.

He was the starting centerfielder in each and every playoff game the Orioles played in in 2012, 2014, and 2016. Jones eventually passed the centerfield torch to current Oriole Cedric Mullins, with the two sharing the outfield in the second half of the 2018 season. An Orioles legend, Jones threw out the first pitch of the 2023 ALDS against the eventual World Champion Rangers.

The impact Jones has had on the Orioles' franchise is readily apparent. But what made the Bedard trade such a home run was that it wasn't just Jones who made an impact in Baltimore. Along with Jones, the Orioles acquired their ace pitcher in the mid 2010s in Chris Tillman.

Indeed, the "Tiller" started 205 games for the Orioles from 2009 through 2018, going 74-60 and earning a spot on the All-Star team in 2013. His best seasons came in 2012 (2.93 ERA) and 2013 (3.71 ERA), though Tillman was an above average starter in 2014 and 2016 as well. The big righthander toyed with a comeback in early 2023 but was left unsigned.

Chris Tillman
Cleveland Indians v Baltimore Orioles / Rob Tringali/Sportschrome/GettyImages

George Sherrill's career in Baltimore was short but effective. Affectionally known as "Flat Breezy," Sherrill was an All-Star in 2008 and developed a reputation as the Orioles' closer of creating significant jams for himself and getting out of them to earn a save. The Orioles traded Sherrill to the Los Angeles Dodgers in 2009 for third-base prospect Josh Bell (not the one currently on the Marlins). Both Sherrill and Bell have been out of baseball for over 10 years.

Mickolio spent parts of three seasons with the Orioles, his best stint coming in 2009, where he appeared in 11 games and pitched to a 2.63 ERA. The Orioles dealt Mickolio to Arizona in a deal for Mark Reynolds in 2011, and he was out of baseball the following year.

Unfortunately for Seattle, Bedard never lived up to the lofty expectations he set up for himself in Baltimore. After going 13-5 with a 3.16 ERA in 2007, Bedard battled injuries with the Mariners, starting only 46 games over 4 seasons in Seattle. Bedard bounced around the league between Boston, Pittsburgh, Houston, and Tampa Bay, with his last appearance coming in 2014.

With the Texas Rangers securing their first World Series in franchise history, baseball's offseason will soon begin in earnest. The Orioles had a terrific 2023 season but need improvements on the pitching and hitting sides of the ball. While true winning trades have been uncommon for the Orioles over the last 25 years, the above five trades remind us that with the right GM, and sometimes a bit of luck, a trade can create a positive impact on a team for years to come.