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The Biggest Free-Agent Mistake The Orioles Must Avoid This Winter

Orioles baseball boss Mike Elias loves to repeat the same mistakes over and over, but our fingers are crossed this tragic roster fetish is out of his system now

Sep 5, 2026; Baltimore, Maryland, USA; Baltimore Orioles pitcher Chris Bassitt (40) walks off of the field during the sixth inning against the Boston Red Sox at Oriole Park at Camden Yards. Mandatory Credit: Daniel Kucin Jr.-Imagn Images | IMAGN IMAGES via Reuters Connect

Mike Elias has a certain type. He goes for it every time.

But with what will be the Orioles ninth season with this baseball failure in charge, something must change. We know he is a stubborn egomaniac, so not much is going to be different. And the hiring of a “GM” isn’t going to change much, either. But perhaps it could the last of this constant mistake.

Could this please be the year that Elias doesn’t find some mid-30s, subpar, probably-going-to-get-hurt-had starting pitcher to waste $13-$19M on? Man, does he have a thing for this, and for a team that is this far from competing that has so many massive roster holes to fill and always runs a limited payroll because the feckless private-equity billionaires who own the team don’t care about winning, repeating this mistake will come at a dire cost.

I’m not saying he can’t try to find a value starter to buttress the middle of the rotation, but only with these caveats attached. Because is the 2027 Orioles have someone who is so clearly an extension of the Chris Bassitt, Zach Eflin, Charlie Morton, Tomo Sugano, Kyle Gibson, Jordan Lyles timeline of failure, it’s not going to bode well for the chances of anything much improving next season.

Those odds are bleak enough with an overmatched Elias puppet running the dugout, and I’m not saying they can’t take a gamble, but only under the following conditions:

1. They Get An Opening Day Starter First

Aug 28, 2026; St. Petersburg, Florida, USA; Tampa Bay Rays pitcher Shane McClanahan (18) delivers a pitch during the third inning against San Diego Padres at Tropicana Field. Mandatory Credit: Pablo Robles-Imagn Images | IMAGN IMAGES via Reuters Connect

So like if you trade for Shane McClanahan, and ideally find a way to extend him, then I don’t care so much what you do to bring in the second starter that you will still badly need. But an elite starter who is clearly better than Kyle Bradish is imperative. That provides some wiggle room for what else follows.

2.     He Can’t Be 36 Or Older

Jul 21, 2025; St. Petersburg, Florida, USA; Baltimore Orioles pitcher Charlie Morton (50) and catcher Jacob Stallings (25) walk to the dugout before the game against the Tampa Bay Rays at George M. Steinbrenner Field. Mandatory Credit: Kim Klement Neitzel-Imagn Images | IMAGN IMAGES via Reuters Connect

Sorry Bassitt, I don’t care how great of a leader you might be and all that stuff, the $19M that went to him last year was always going to be a disaster. When a playoff team the year before – Toronto – moves a pitcher to the pen for their pennant push, trying to coax 180 innings out of hm on a bloated contract cannot continue to be the norm here. We need some age limits.

3.     He Should Make Less Than $10M a year

Oct 22, 2026; Milwaukee, WI, USA; Milwaukee Brewers starting pitcher Brandon Woodruff (53) speaks during a workout session before the 2026 World Series. Mandatory Credit: Benny Sieu-Imagn Images | IMAGN IMAGES via Reuters Connect

This is why a guy like Brandon Woodruff would really interest me, or why I was pushing for Dustin May last offseason. Woodruff is older and has injury issues, but he’s not going to get the kind of silly money Elias paid guys like Eflin and Morton. Even Sugano at $13M was too rich for that profile. Take the risk for someone with more risk from an injury standpoint if you must, but for less money and with a much better body of work.

4.     He Better Not Have Worn This Uniform Before

Aug 31, 2025; San Francisco, California, USA; Baltimore Orioles starting pitcher Tomoyuki Sugano (19) wipes his face as he leaves the field for a reliever during the fourth inning against the San Francisco Giants at Oracle Park. Mandatory Credit: D. Ross Cameron-Imagn Images | IMAGN IMAGES via Reuters Connect

Man does Elias enjoy this part of the equation. It’s not bad enough most of the pitching signings already check the above boxes, but we had to get Gibson for one than one stint and Eflin flaming out at $19M and needing back surgery wasn’t enough to keep Elias from re-signing him.

He did it with Andrew Kittredge and got more lucky with it than not in 2026, but that was tempting fate especially with the early IL stint for the aged reliver.  It’s like he so wants to prove he was right all along that he keeps throwing bad money after bad and instead of actually upgrading.

It’s time to get real. Don’t even think about Bassitt, or Eflin or Sugano (who was half-decent for the Rockies last year (and they only paid him $5M).

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