With the trade deadline fast approaching, the Baltimore Orioles are once again expected to be buyers. Reigning executive of the year Mike Elias

has made many moves that have been fantastic for the Birds, but even the best executives swing and miss sometimes.

With the Orioles looking to help a tiring starting rotation at the 2023 trade deadline, the Birds decided to see if they could help Jack Flaherty turn his season around. Flaherty had shown the ability to be a very good pitcher in St. Louis, as well as the ability to be a high volume pitcher which is exactly what the Orioles were looking for.

The trade looked great at first as Flaherty earned a win with a quality start with eight strikeouts against the Toronto Blue Jays, but it was downhill from there. Flaherty took the loss in his next two starts, including a drubbing in San Diego where he gave up seven earned runs in 3.0 innings.

Over his next four starts, Flaherty allowed 12 earned runs in just 16.2 innings with a record of 0-1, which would have been worse had the Orioles offense not saved him. After that, Flaherty was moved to a bullpen role for the remainder of the regular season. He was solid in that role but it was too little too late. Flaherty’s contract expired at the end of the season and the O’s chose not to resign him.

Trading for Jack Flaherty was one of Orioles’ GM Mike Elias’ biggest mistakes

In order to get Flaherty, the Orioles traded away their #16 prospect, INF César Prieto, their #18 prospect, LHP Drew Rom, and RHP Zack Showalter. Rom quickly joined the Cardinals starting rotation but did very poorly. He made eight starts earning a 8.02 ERA for the season, but he did make one good start. Rom pitched a career high 5.1 innings while striking out a career high seven batters and allowed zero runs to earn his only career win to this point in a game against the Orioles.

Prieto and Showalter are both having very good seasons in the Cardinals’ farm system. Prieto looks like he could be called up any day, while Showalter continues to develop in single-A. Rom has yet to pitch this season due to left shoulder biceps tendinitis, but he’s a good looking prospect that isn’t arbitration eligible until 2027.

To make the O’s feel even worse about the trade is Flaherty, who signed with the Detroit Tigers in the offseason, has returned to form. In 15 starts this season he’s got a 3.24 ERA and his 115 strikeouts (10 more than Corbin Burnes and Grayson Rodriguez) are tied for 13th in all of baseball. Numbers that would have been a big help to an Orioles rotation that has been decimated by injuries.

The trade for Flaherty was justifiable at the time but it flopped for the Orioles. Elias is a great GM and the majority of his moves have worked out very well. I can’t wait to see what he does during this season’s trade deadline.