Orioles baseball boss Mike Elias has never won a playoff game and it’s quite fair to wonder if he ever will after his team has had successive seasons falling 18.5 and 19.5 off the pace in the AL East.

That’s the division that features the Rays, a franchise that has utterly undressed Elias for eight years with smaller budgets and less resources and that has repeatedly thrashed him in trades and is built for long-term success. And the Yankees and Red Sox were in the playoffs and the Blue Jays were in the World Series last year, so good luck. We’ll see how much hiring a “GM” in name only but not power, changes anything, but we aren’t holding our breath.

There are no shortage Elias’s former players and prospects all over these World Series rosters and he’s done some of his most significant business with these two franchises, including an absolutely blockbuster trade for Corbin Burnes from the Brewers and then throwing prospects at the Rays for middling starter Shane Baz as if he was Corbin Burnes. He likes their players in general and likes doing business with them and we strongly believe those trends should continue … hopefully with vastly different results. (Honestly he probably deserves a ring from the Rays).

We’ve long circled some strategic options for the 2027 Orioles off what are now the World-Series rosters, and these are names to keep an eye on when the final series of the season is over and MLB free agency/trade season begins in earnest:

Shane McClanahan (Trade)

The Rays former Cy Young starter isn’t pitching in the postseason and got shutdown in September but he showed us more than enough in his comeback from surgery to be the top starting pitching trade target for Elias. A lefty with a prototypical build and electric stuff who knows how to pitch (not just some thrower) who has dominated at Camden Yards and shown he go up against the best starters on the Yankees or Red Sox and outduel them.

We’ve been making the case for this Baltimore native since the moment the season ended, our much-smarter buddy Dan Syzmborski, pioneering project data analysts at Fangraphs.com and lifelong Orioles fan agrees a one-year rental here (a la Burns before) makes too much sense not to vigorous explore (he explains as much on “The Daily Flock Show” below).

Freddy Peralta (Free Agent)

We were hopeful that Peralta’s rough time with the Mets, prior to his late-season trade to Tampa, might suppress his value some. The overall regular season marks wouldn’t look nearly as good as what he did his entire career with the Brewers – make 30 starts and post a 3.50 ERA.

He is young enough and durable enough, but after an ALCS for the ages, adding to an already nice playoff resume, this might be closer to $30M/season than $20M. It’s still precisely what the Orioles need to be their top starter for 2027. Would still leave them short a lefty, unless they dealt for McClanahan and did this.

Brandon Woodruff (Free Agent)

He was once a co-ace with Burnes before the injuries mounted. But this was a bulldog and he gets every part of the job and will do as much as his body allows and should come fairly cheap. Szymborski is sufficiently intrigued and I once begged Elias to add Woodruff as well when he did deal for Burnes, because he was still a starter short.

He only made nine starts this season and he’ll be 34, but in 2025 he was stud again (3.17 FIP). He hasn’t thrown 70 innings in a season since 2022, I get it. He was good for 150/year prior to that, the O’s let Kyle Bradish go over 150 IP after not throwing 40 either the previous two season and they have a lot more invested in him than what this would cost.

They are always making a quasi-value play (Chris Bassitt, Zach Eflin, Charlie Morton, Tomo Sugano, Kyle Gibson, Jordan Lyles) and most have been vastly overpaid. But a two-year deal with Woodruff (protection is 2027 is rough) might be in their wheelhouse as the second starter they add this offseason.

Joey Ortiz (Trade)

If they trade Gunnar Henderson, which absolutely should be the case but might not happen until the trade deadline, getting this 2019 draft pick back to be a dominant glove-first shortstop would be smart. He was dealt in the package for Burnes, and the Brewers are overflowing with elite infield prospects and they are always churning the bottom part of their roster.

He would totally alter the spine of the Orioles and if, say, paired with Jordan Westburg at second, that could do wonders for the infield defense. Either way the IF needs to be rethought and a glove of this magnitude would be perfect. (And if Tampa doesn’t pick up the option on its Gold Glove caliber shortstop, Taylor Walls, he should be on Elias’s radar, too).

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