Years ago, Chris Davis received the largest free agent contract the Orioles have given out — a claim that will remain intact for another year.

His seven-year, $161 million deal signed about nine years ago this week wasn’t topped this winter. To be perfectly honest, I would have lost money betting that it would fall, given the cost of free agent pitching and the Orioles’ desire to add a stud to the top of their rotation.

For a variety of reasons — though to me, not a lack of effort — that didn’t turn out to be the case. I don’t think they’re sticking to short-term deals because of how Davis’ contract went (though I think the aversion to paying players long term in their 30s broadly applies across the league because of stories like his).

But if we’re talking about true regret, and past free agency playbooks that the Orioles should avoid, it’s one that’s potentially weeks away from playing out.

It’s not paying an aging slugger; this team really has no need for one and wouldn’t do that anyway. It’s waiting out the high-ish end of the starting pitching market and giving the stragglers a home in Baltimore.

Ahead of the 2014 season, Ubaldo Jiménez and the Orioles paired up together at the end of the offseason, with his February deal worth four years and $50 million, still the largest they’ve given out to a free agent pitcher. Yovani Gallardo signed a two-year deal in February 2016, and in 2018, Andrew Cashner and Alex Cobb signed late in free agency.

You can make a case that Jack Flaherty is better than all of them, or that the kind of contract that lefty Andrew Heaney might command wouldn’t really be too onerous, especially for a team that, in the words of Jean-Ralphio Saperstein, is flush with cash. Those things are probably all true.

Sometimes, the market tells you what you need to know, and that the Orioles targeted other starters — Tomoyuki Sugano and Charlie Morton — instead of those others still available who have done the business they want to. For me, the threshold for acquiring a starting pitcher at this point, given what the Orioles have already built, is that he’d have to deserve to start opening day. I’m not sure anyone left on the free agent market would be chosen over Zach Eflin or Grayson Rodriguez, and for that reason, it’s trade or bust when it comes to starting pitching acquisitions.

Sure, there’s value to be found at this stage in the market. Players (and their families) get antsy and want to know where they’ll be during the season, let alone spring training, and deals start to come together. The Orioles would probably argue there was value to be found earlier this winter too, and they identified it.

Listeners of our podcast — which I’m now co-hosting with Paul Mancano at least weekly — know it has been a grind to articulate what I think about this Orioles’ offseason. I don’t think it’s fair to let them off the hook for not having a Corbin Burnes-like substance atop the rotation, given how much having him meant in 2024, but I also appreciate what they did do and why they did it. The Orioles won’t be better for what they did this winter, but they certainly protected against being worse in a lot of ways, and that matters.

All that is to say there may be some regret about players who aren’t going to be on the Orioles’ opening day roster, but they probably won’t lament the moves they did make. There will likely be no Davis-sized contract on their books for years to come, at least not a free agent one, based on this winter’s activities. That’s all well and good. It’s those spring training starting pitchers who they have to avoid now.

👀 Free agent of the week

I wish I could say there was a method to the madness, but add Jeff Hoffman to the list of players highlighted in this space who almost immediately sign. I’ve tried to use my powers for good regarding Austin Hays and Anthony Santander, but to no avail. Allow me to do John Means now.

I don’t know how much he’ll end up pitching as he recovers from another elbow surgery, but there’s a long track record of him being really good when he’s on the mound. My gut tells me there’s probably a deal out there for him once spring training begins and teams can utilize the 60-day injured list, making it so Means isn’t taking up a roster spot in the interim. I hope it’s a good one for him and his family.

📰 For further reading

💔 More details on Matusz: The passing of Brian Matusz last week was just plain sad. The tail end of his time with the Orioles was the beginning of my time around the team, so I didn’t really know him, but it’s clear what an impact he made on those who did. Danielle has done a wonderful job chronicling it all, including this update from Monday. (The Baltimore Banner)

🏆 Orioles quarter-century team: I was quite interested to see who made MLB.com’s quarter-century team for the Orioles. I wonder how many current Orioles will be on the half-century team? Gunnar Henderson, Adley Rutschman, maybe Grayson Rodriguez or Kyle Bradish? There are plenty of candidates. (MLB.com)

✍️ Analysis on signings: Danielle had a good update on the Orioles’ progress on the international front, with another class of players set to sign this week. I can say from my Baseball America rankings experience that the impact of the players Koby Perez and his team are going to sign will only grow this year. (The Baltimore Banner)