The 5 most impactful trade deadline moves in Orioles history

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.