We have officially witnessed 25 seasons of Major League Baseball since turn of the century, and it has brought a considerable amount of movement for the Baltimore Orioles.
From blockbuster trades and the start of rebuilds, to signings of legendary players and division-winning runs, the Orioles have made moves that have both helped and hurt the franchise over the last 25 years.
In this piece, we discuss the five best trades the Orioles have made since the year 2000. Let’s start with the most recent of the five.
2019: KYLE BRADISH

The 2019 season was not great for the Orioles, to say the least; it was the first season that the O’s were in a true rebuild and finished with a record of 54-108.
After that season, the Orioles decided to trade former fourth overall selection, right-hander, Dylan Bundy to the Los Angeles Angels for a total of four prospects, all right-handed pitchers.
The players acquired were Kyle Brnovich, Isaac Mattson, Zach Peek and Kyle Bradish.
Brnovich was released by the Orioles in August of 2025 and is now a part of the Colorado Rockies organization. Peek was selected by the Milwaukee Brewers in the minor league phase of the Rule 5 Draft in 2024. Mattson made his big league debut in May of 2021 and pitched a total of four games with the Orioles, carrying a 6.23 ERA before getting released in May of 2022.
Bradish made his debut with the Orioles in 2022, when he pitched to a 4.90 ERA in 23 starts and over 117 innings. After the 2022 season, Bradish would turn into a front-line starter in, going 12-7 and carrying a 2.83 ERA in 30 starts during the 2023 season.
Bradish pitched a total of 168.2 innings, gave up 53 earned runs, walked just 44 batters and struck out 168. He also received votes for the Cy Young Award, finishing fourth in the AL.
Bradish would, unfortunately, miss a majority of both the 2024 and 2025 seasons due to Tommy John and would return in August. For the 2024 and 2025 season, Bradish would post a 2.65 ERA in 14 combined starts. He would pitch 71.1 innings but would give up just 21 earned runs, walk 25 batters and strike out 100.
Bundy would pitch a total of 63 games after the trade between the Angels and Minnesota Twins, retiring from baseball after the 2022 season.
2010: J.J. HARDY
After going 66-96 in 2010, the Orioles were continuing on an unfortunate downward spiral.
The team just completed their 13th straight losing season, but the Orioles hired their third manager of the 2010 season, giving Buck Showalter a chance, with young players like Matt Wieters and Adam Jones beginning to show true promise.
The O’s made a move that offseason to bring in a former All-Star shortstop, as the club dealt Brett Jacobson and Jim Hoey to the Twins in exchange for Brendan Harris and James Jerry Hardy.
In his seven seasons with the Birds, Hardy slashed .252/.293/.398 with a .690 OPS over 889 games. He collected 854 hits, 168 doubles, three triples and 107 home runs while having four straight seasons from 2011-2014 where his WAR was 3.1 or higher, making him one of the most valuable Orioles during that period.
Hardy was also an All-Star in 2013 and is a part of one of the most iconic moments in Orioles history as the third run scored on Delmon Young‘s double in the eighth inning of game two of the 2014 ALDS.
Hardy decided that it was time to hang up the cleats after the 2017 season. He is now an Orioles Hall of Famer thanks to his contributions to the O’s stretch of contention in the 2010s.
2011: CHRIS DAVIS

The Orioles traded their closer Koji Uehara, who, at the time, had a 1.72 ERA over 65 innings, to the Texas Rangers for right-hander Tommy Hunter and infielder Chris Davis.
Davis played for the Orioles from 2011-2020 and became one of the best power hitters of the 2010s, playing in 1,151 games and slashing .230/.318/.459 with a .777 OPS. He totaled 941 hits, 178 doubles, two triples and 253 home runs during that span.
Davis is also the holder of many franchise records, including the most home runs by an Oriole in a season, hitting 53 of them in 2013. They lefty slugger would become All-Star in 2013, win a Silver Slugger and finished two seasons with AL MVP votes, placing third in 2013 and 14th in 2015.
Davis being traded to the Orioles was supposed to help the Rangers make a postseason run by upping their bullpen, which actually happened. However, it also turned out to be a deal that helped contribute to the Orioles making three postseason appearances in a five-year span.
2000: MELVIN MORA

The year is 2000, and the New York Mets are making a run at the NL East title.
New York decides to eye up infielder Mike Bordick from the Orioles, who has an .831 OPS and is currently batting .297 in 100 games at the time. The 34-year-old Bordick was traded on July 28 to the Mets for utility player Mike Kinkade, right-handers Leslie Brea and Pat Gorman and infielder Melvin Mora.
Kinkade played in 64 games over two seasons with the Orioles, posting a .255 average with a .781 OPS. Brea pitched eight total games over two seasons and carried a 12.27 ERA in just 11 innings, and Gorman never made the big leagues.
When Mora came over, he only had a 0.3 career WAR and was struggling offensively, but he would turn into a huge impact player for the Orioles during some dark seasons.
Mora played from 2000-2009 with the Orioles and slashed .280/.355/.438 with a .793 OPS. He earned 1,323 hits, 252 doubles, 12 triples and 158 home runs and was a two-time All-Star during this time, won a Silver Slugger and finished 18th in AL MVP voting during the 2004 season.
2008: ADAM JONES

In February of 2008, the Seattle Mariners went for a guy who showed out with a 3.16 ERA the year prior and finished fifth in Cy Young voting, O’s left-hander Érik Bédard.
Seattle would send right-handers Chris Tillman, George Sherrill and Kam Mickolio, lefty Tony Butler and outfielder Adam Jones in exchange for Bédard’s services.
Butler would not make it to the majors. Mickolio spent three years with the Orioles and carried a 4.32 ERA and would not even receive a win in 29 career games. Sherrill would be the O’s closer for two years, posting a 3.71 ERA in 99 games and finishing with 51 saves.
Tillman would become the ace of the Orioles from 2010-2018, holding a 4.57 ERA in 205 starts and becoming an All-Star in 2013.
Jones would play for 11 years in Baltimore and slash .279/.319/.459 with a .777 OPS. He totaled 1,781 hits, 305 doubles, 27 triples and 263 home runs in orange and black and would receive MVP votes in three seasons, finishing sixth in 2012, 13th in 2013, when he would also earn his only Silver Slugger, and 14th in 2014.
Jones was the face of the Orioles for a little over the decade. He is an Orioles Hall of Famer and now works in the front office of the organization that embraced him and gave him an opportunity all those years ago.
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