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.

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.