While Baltimore may not end up playing in the deepest end of the free agent pool when it comes to pitchers, this isn't a team that should just be targeting roster filler types for their starting rotation. This is an organization that should be expecting to be viable World Series contenders for the foreseeable future and that means their starting pitching is going to have to match up with the best of the best in a short series. One of the clear names that Baltimore should go after before the 2024 season with that goal in mind is Jordan Montgomery.
Montgomery doesn't have the sexiest stuff and doesn't command headlines, but he just puts up results year in and year out. He is currently working on his third straight season of putting up 2.7 fWAR or better and was one of the jewels of the trade deadline when the Rangers traded for him. He doesn't give up walks, does a lot of things pretty well when it comes to his peripherals, and is basically a mortal lock to put up a mid-3 ERA each season. He won't be cheap to sign as he will likely seek a raise per year from the $10 million he is taking home in 2023, but should still be reasonable enough for Baltimore to be able to get a deal done.
It does look a little weird to talk about the Orioles not going after the top of the market and then turning around and suggesting that Baltimore go after one of the top pitchers in the AL this year in Sonny Gray. However, Gray is a unique case where the current state of Orioles matches up surprisingly well with where Sonny is in his career.
Gray has been the second best pitcher in the American League this season by fWAR at 4.0 behind only the Blue Jays' Kevin Gausman. Perennially underrated, Gray is another one of those guys that just does a lot of things well and puts up results every season. He is also another guy that is not likely to come cheap, but he has also surprisingly floated the idea of retiring after this season which doesn't exactly point to a guy wanting a long-term deal. Assuming he does play which still seems likely, the Orioles could give him a shorter deal with some player options that could a appeal to a guy like Gray that may want some career flexibility while also playing on a very competitive team in the short-term.