It’s been five weeks since the Los Angeles Dodgers hoisted their second consecutive World Series trophy, and the Orioles are a little closer to having a team that can compete for their first World Series title in 40+ years. Coming into this offseason, the consensus shopping list for Baltimore featured 1) a frontline starter, 2) an impact power bat, 3) a closer to spell the once-again-injured Félix Bautista, and 4) even more starting pitching.

Over a month into the offseason, and that shopping list has at least some check marks. Ryan Helsley was the Orioles’ first major signing of the offseason, signing a two-year, $28M deal to try and fill Bautista’s large shoes. In the power department, they added Taylor Ward after a breakout, 36-home run campaign with the Angels—though it cost Baltimore oft-injured starter Grayson Rodriguez. These are steps in the right direction, but with no new starting pitchers on board, the strides are more Altuve-sized than Judge-sized.

With the Winter Meetings currently underway in Orlando, there are plenty of rumors swirling about the big steps on the horizon for the O’s. As we learned last offseason, a world of possibilities can mean you end up with the worst possible outcome, the one where you replace Corbin Burnes with a 41-year-old on the brink of retirement and a 35-year-old Japanese import with zero Major League experience.

Mike Elias & Co. now have a chance at a do-over as the Orioles look to return to contention in 2025. With plenty of big free agents still on the board, I break down the best, worst and middle ground scenarios for the remainder of the Orioles’ offseason.

The absolute best-case scenario

Trade for LHP Tarik Skubal and sign OF Kyle Tucker

When it comes to Skubal—the two-time reigning AL Cy Young winner—there are plenty of question marks. The first question is whether the Tigers would actually explore a trade for the best pitcher in baseball. Tigers President of Baseball Operations Scott Harris didn’t exactly shut down the possibility of trading their ace in a recent interview with MLB Network, saying, “My job is to make this organization better, which means that I need to listen to every opportunity.”

That brings us to the question of what it would cost to acquire the 29-year-old left-hander. Assuming Detroit is willing to listen to offers for Skubal, they’ll have to balance the fact that the ace only has one year left of team control with the fact that he’d be the first reigning AL Cy Young winner to be traded since Roger Clemens in 1999. When the Orioles acquired Burnes, he was in a similar contract situation, entering his last year of arbitration.

That lack of long-term team control, and the fact that the Brewers missed the playoffs in 2022, meant that Baltimore got Burnes for only a pair of fringe major leaguers and a draft pick. Skubal would undoubtedly be more expensive to acquire. Detroit would likely ask for a major-league-ready player like Jackson Holliday or Samuel Basallo as well as several top prospects. It’d be a hefty price to pay, especially when Skubal would also need a $40M+/yr contract if the Orioles want to extend him. But there are zero questions about how Skubal would transform the Orioles’ rotation, meaning if the lefty is truly available, the O’s should echo Harris and listen to every opportunity.

And what’s better than adding the best pitcher in baseball? Adding the top free agent bat along with him. Tucker would be easier to acquire in that Baltimore would only need to outbid all other teams for his services. Elias has ties to the All-Star OF, having been Houston’s scouting director when they drafted Tucker in 2015. If the O’s front office can leverage that connection into Tucker’s signature on a big contract, it’d level up an outfield that currently features only unproven or inconsistent players.

Adding two $40M/yr players is probably beyond this front office’s capabilities, even if Elias claims they have the budget to add “both an impact bat and frontline starter.”

The good, realistic scenario

Sign one of LHP Framber Valdez or LHP Ranger Suárez and one of Tucker, DH Kyle Schwarber, or 1B Peter Alonso

After Dylan Cease signed with the Blue Jays, Valdez and Suárez became the top two free agents in the starting pitching market. Both have also been linked to the Orioles over the past several days. MLB Network insider Jon Heyman specifically named the O’s as one of the teams looking to sign the former Phillies left-hander, Suárez. Like Tucker, Valdez has ties to Elias thanks to their shared time in Houston and MLB.com reports the Orioles and Mets are favorites to land the two-time All-Star.

Both the free agent lefties represent a significant step down from a pitcher like Skubal, but would undoubtedly help reinforce the Orioles’ rotation. Both were All-Stars as recently as 2024 and had strong first halves in 2025 before fading after the All-Star break.

Either would be a good, but not great, signing, however. While they both have more proven track records than Kyle Bradish or Trevor Rogers, it’s hard to definitively say they’re better than the O’s current top two starting pitchers. When the Orioles added Burnes two years ago, they knew they were getting an A-level pitcher. With Valdez or Suárez, they’d be getting more of a B/B+ starter to match Bradish and Rogers. That’d certainly be enough to get this rotation back to playoff-worthy, though it will also leave fans and the greater baseball public wanting more.

The O’s could satisfy that desire for more by adding one of the premier power bats. ESPN’s Buster Olney reported yesterday that the Orioles, along with the Phillies and Pirates, were one of the teams competing for the signature of the lefty slugger Schwarber. This came on the heels of Heyman’s report that the O’s and Red Sox met with Alonso at the Winter Meetings.

Pitching is perhaps a bigger priority, but after dropping from 4.9 runs/game across 2023 and 2024 to 4.2 runs/game in 2025, adding a big bat to the lineup could help the O’s win a lot more ball games. Sure, the fit with these guys might be a bit clunky given the 1B/DH/Corner OF’s already on the roster. But if Elias is really committed to improving the roster, those bats will do just that.

Calling this the “Charlie Morton/Tyler O’Neill 2.0” scenario would perhaps be too harsh, but anything close to a repeat of last winter’s offseason will immediately send Birdland into another spiral of disappointment, bitterness and cynical “I told you so’s”. Sure, names like Max Scherzer and Justin Verlander or Paul Goldschmidt or Marcell Ozuna may sound appealing at first thought, but Baltimore should be trying to build a roster for 2026, not 2016. All indications are that the first big wave of free agent/trade activity will come during this week. If the consensus around Birdland at the end of the week is that the Orioles missed that wave again, the worst-case scenarios will start to feel more and more likely.