The 5 most impactful trade deadline moves in Orioles history

2. July 29, 1988: Mike Boddicker for Brady Anderson, Curt Schilling

12 seasons later, the Orioles cut a deal with another division rival: the Red Sox. The O's acquired outfielder Brady Anderson and pitcher Curt Schilling for starting pitcher Mike Boddicker.

Boddicker pitched well for the Red Sox in the regular season, putting together a 3.49 ERA. However, in Game 3 of the 1988 ALCS, he gave up six runs in 2.2 innings. Then, in Game 3 of the 1990 ALCS, he gave up four runs (two earned) in eight innings. He took the loss in both outings and the Sox were swept by the Athletics in both series.

Curt Schilling only pitched a few seasons for the O's before being traded away to the Astros, which turned out to be an undeniably bad trade.

But, Brady Anderson gave the Orioles 14 good seasons. He put up a .794 OPS, hit 209 homeruns, stole 307 bases, and was named an All-Star three times. He also played great in the 1996 and '97 playoffs, averaging a .955 OPS with six homeruns and 12 RBIs across 19 games. So, despite losing Schilling, this was another good deal for the O's.

3. July 30, 2011: Koji Uehara for Chris Davis, Tommy Hunter

At the 2011 deadline, the O's gave up reliever Koji Uehara for two young Texas Rangers named Chris Davis and Tommy Hunter.

Uehara went on to be solid out of the bullpen for the Rangers, Red Sox, and Cubs. He pitched to a 2.66 career ERA but did not even pitch ten seasons before retiring, so he was not much of a loss.

On the other hand, the O's got one of the best first basemen in baseball in Chris Davis. He hit 253 homeruns as an Oriole, compiled a .777 OPS, and was named an All-Star in 2013 — the same year he finished with a career high 53 homeruns and 138 RBIs. While Davis struggled through injuries in his final seasons and cost the Orioles with his massive contract, he gave them some productive seasons and many, many moonshots.

Across his Orioles tenure, reliever Tommy Hunter pitched to a 4.16 ERA. This included a stellar 2013 and '14, in which he pitched to a 2.81 and 2.97 ERA respectively. Even though their team struggled as a whole, this was a great trade for the Birds because they got more production than they gave up.

4. July 18, 2018: Manny Machado to Dodgers for five prospects

In 2018, the struggling Orioles underwent a massive sell. This, of course, included the blockbuster that sent Machado to the Dodgers. In return, the Orioles received five prospects: Yusniel Diaz, Dean Kremer, Rylan Bannon, Breyvic Valera, and Zach Pop. Six seasons later, how did this trade pan out?

Four out of the five players did not pan out, but one name should sound familiar: starting pitcher Dean Kremer. Since his debut in 2020, Kremer has pitched to a 4.32 ERA with the O's. Certainly not an ace, but a serviceable starter who has provided them valuable innings and will continue to do so down the stretch. And, considering they would have lost Machado to free agency after 2018, it was a smart move for the O's.

5. July 24, 2018: Zack Britton to Yankees for trio of pitchers

Finally, less than a week after dealing Machado to the Dodgers, the Orioles sent Zack Britton to the Yanks for pitching prospects Dillon Tate, Cody Carroll, and Josh Rogers.

Carroll and Rogers did not pan out for the O's, but Tate is still on their roster. Across his Orioles tenure, he has a compiled a 4.07 ERA out of the 'pen and gave them some solid stretches. However, he was sent down to Triple-A this season, as he pitched to a 4.59 ERA and has not looked sharp.

Britton did battle some injuries with the Yankees but pitched to a 2.75 ERA across five years, so the Yanks probably won this trade. However, similar to the Machado deal, the O's were going to lose him to free agency anyway so it made sense to dump him.

From the 1976 blockbuster to the 2018 deadline sell-off, it's clear that it takes time to fully evaluate the strength of a trade. While it took seven years, 3 of the 5 players received in the Yanks trade served as key pieces on a World Series-winning roster.

Similarly, it has taken some time for Kremer to establish himself. But now, more than five years later, it seems that the Machado trade produced one of the key cogs in the Orioles rotation.

So, should the Orioles make any large splashes before tonight's deadline, it will be important to be patient, withhold immediate judgements, and let time tell the real story.