5 massive missed opportunities Dodgers squandered at trade deadline

LHP Jordan Montgomery

The only blockbusters the Dodgers would've attempted would've been for starting pitchers. LA has been in dire need of starting pitching ever since the rookie starters first entered the rotation.

Jordan Montgomery fits in that role well, and is used to the big moments, as he was with the Yankees from 2017 until the 2022 trade deadline, when New York dealt him to the Cardinals in exchange for outfielder Harrison Bader. Montgomery adapted well to his new environment in St. Louis, posting a 3.11 ERA and 4.69 K/BB with the Cardinals. While Montgomery's walk numbers have gone up this year, his strikeout numbers have gone up too. The increases do not quite cancel each other out, but Montgomery has still been good enough to post a 3.42 ERA this year.

The left-hander was traded in a package deal, along with reliever Chris Stratton, to the Texas Rangers in exchange for LHP John King and two top prospects: RHP Tekoah Roby, who is now the Cardinals' No. 4 overall prospect, and INF Thomas Sagesse, who is now the Cardinals' No. 8 overall prospect. That return was significant, so it's possible that the Dodgers were in on Montgomery and backed out because of the high asking price, similar to the reports of what happened with a potential Nolan Arenado deal. But, the Dodgers trading players that would rank similarly wouldn't have been as costly as it appears on the surface due to the ridiculously deep farm system they have.

The Dodgers' top seven prospects are all in the top 85 in the majors, whereas none of the pieces in this trade were in the top 100, according to MLB Pipeline. That means the Dodgers wouldn't have had to trade one of their most coveted prospects to get a deal done for Montgomery. Losing out on Montgomery has an even larger significance after the Dodgers could not get LHP Eduardo Rodriguez from the Tigers because he used his 10-team no-trade clause to veto the trade. The Dodgers had to turn elsewhere to get help as a result, but failed to acquire either Dylan Cease or Jack Flaherty to fill the starting rotation before the trade deadline had passed, and instead settled on Ryan Yarbrough.