The 5 most impactful trade deadline moves in Orioles history

With the 2024 MLB trade deadline just hours away, the AL East-leading Orioles have been among the main group of teams expected to make some moves. They have already bolstered their rotation with the trade for Rays' Zach Eflin, but Jon Heyman reports they are still pursuing pitching help.

If the Orioles went all in and traded for Tarik Skubal, Garrett Crochet, or another stud pitcher on the market, it would be a huge deal for a team that is poised to make a playoff run.

So, as the Orioles look to make final touches to their playoff-bound roster, let's take a look at five of the biggest Orioles trades made before the deadline.

1. June 15, 1976: 10-player blockbuster with Yankees

In 1976, the two division rivals agreed on a massive, 10-player trade. The Yankees sent Rick Dempsey, Tippy Martinez, Scott McGregor, Dave Pagan, and Rudy May to the O's in exchange for Doyle Alexander, Elrod Hendricks, Grant Jackson, Jimmy Freeman, and Ken Holtzman.

As time passed, it became clear that the O's were the clear winners of the megadeal. While the Yanks did not get much production out of any of the five players they received, the O's received a longtime catcher, starter, and reliever in the deal.

Dempsey was the catcher for the Orioles for 12 seasons and, most notably, won the 1983 WS MVP when he went 5-13 with four doubles, a homerun, and two RBIs.

McGregor was a starter on the O's for 13 years, pitching to a 3.99 career ERA. He also pitched two games in the World Series, and his scoreless, 9-inning Game 5 performance secured the championship for the O's.

Finally, Martinez was a reliever for the Orioles for 11 seasons, pitching to a 3.46 ERA. He was also stellar in the 1983 playoffs, giving up only one run in nine innings and closing out wins in Games 3 and 4 of the World Series.

This trade very clearly helped them win one of their three World Series rings, so it may go down as the single best trade in O's 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.