When the Orioles signed Kyle Gibson on the eve of the winter meetings last year, they were getting a jump on what was expected to be a red-hot and deep pitching market. It was also expected to be one of several moves the team made toward upgrading its rotation, and while they were active in pursuing free agents after Gibson signed, the Cole Irvin trade wasn’t what anyone envisioned as the next big move when Gibson signed in early December.

The pitching market has been heating up early again this year — with Gibson once again involved — but only in the last few days has it started to involve pitchers the Orioles might consider upgrades to their rotation. That’s a sign that even though winter meetings are still just under a week away, every day matters as the Orioles look to improve a rotation that could be key to replicating their 2023 division title.

Gibson and Lance Lynn signing with the St. Louis Cardinals on one-year deals earlier this month represent the exact kind of deal that it would make sense for the Orioles to avoid. While there’s no risk in a one-year deal for a veteran starter who can eat innings, as they saw with Jordan Lyles in 2022 and Gibson last year, there’s limited upside as well.

The Orioles aren’t exactly flush with starting pitching depth, but their aims are now higher than they have been, and the prevailing thought is they’re seeking a pitcher who could start one of the first two games of a playoff series, no matter how well Kyle Bradish and Grayson Rodriguez sustain their improvements from 2023.

The reality is that there are a finite number of those pitchers available on the market, and each one that finds a team that isn’t the Orioles is going to make the club’s situation a bit more untenable.

It’s unclear if Kenta Maeda, who signed on Sunday to a two-year, $24 million deal with Detroit, would qualify as an upgrade for the Orioles. He misses bats, to be sure, but isn’t one to go super deep into games at this stage in his career and, at age-35, might not be exactly the type of workhorse at the top of the rotation the Orioles are seeking.

Sonny Gray likely would have been, though. The All-Star and Cy Young runner-up signed a three-year deal worth $75 million with the Cardinals that reportedly has a fourth-year option that could bring it to $100 million. While paying for a pitchers’ career year in his age-33 season can have its pitfalls, Gray has spent essentially his entire career as a durable starter who knows how to pitch effectively with his whole arsenal — and get results.

He would have been a ceiling-raiser for the Orioles — the type of pitcher who at his best can elevate above everyone else without sacrificing any of the floor the club had with the innings-eater types in that veteran rotation spot before. As someone who has reinvented himself countless times, be it through pitch design or adjustments to how often he throws certain pitches, he could have been a vital asset to the Orioles’ up-and-coming pitchers as they progress in their careers.

So why is Gray not on the Orioles now? Perhaps on a basic level they just weren’t interested, which would be hard to understand, considering he’s one of the top five starters on the free agent market, another one (Aaron Nola) has already signed, and these types of pitchers are a scarce commodity this winter.

Perhaps they were interested and an average annual value of $25 million was beyond their valuation of Gray, especially as the deal progresses. That’s certainly possible — and we know that the next time this front office contradicts its valuation model in any significant way will probably be the first.

Or, perhaps, we are just going to be left curiously wondering what the actual plan is after any starting pitcher of note signs this winter. It’s still early, and the Orioles have plenty of time to execute their plan, but Gray signing so quickly makes me wonder if the plan might end up not relying on free agency in any meaningful way — or at least domestic free agency.

It remains true that the Orioles have the prospect capital to acquire Corbin Burnes from the Milwaukee Brewers or Dylan Cease from the Chicago White Sox — two of the top trade candidates — and same goes for Tampa Bay’s Tyler Glasnow, though it’s probably not the best business to be trading prospects to a division rival. Perhaps if the Orioles were able to pry a top reliever from either of those teams with more than one year of club control, they’d be more comfortable paying the prospect price, and can solve both of their main offseason problems in one move.

There’s also international free agency to consider. Winning a bidding war for Japanese star pitcher Yoshinobu Yamamoto would be quite a coup for the Orioles and a statement from John Angelos that he is willing to support the team’s ambitions. But until something on that scale happens, it’s probably not worth considering.

What is more realistic is Japanese left-hander Shota Imanaga — who has shown the ability to miss bats and stay healthy his entire career, and has the added benefit of bringing opposing right-handers into the lineup to hit into Camden Yards’ cavernous new left field. There was also the interesting reports out of Japan that right-hander Naouki Uwasawa had a contract offer from the Orioles, though he profiles more as a back-end type as his velocity and strikeout numbers on the surface don’t look as good as his career 3.19 ERA.

The reality is there are options. That’s not going to make it feel any better when the free agency alerts come through for pitchers signing with teams that aren’t the Orioles. When a pitcher who can truly be an upgrade gets crossed off the list, it’s not like another one is going to magically appear.

Fans have every right to be anxious until the goal of adding a top starter is achieved. The front office surely feels the pressure, too, knowing the opportunity in front of this team — and the challenge that supporting it by upgrading the rotation will present.