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.