Ryan Helsley, the first significant free agent signing of what’s expected to be a busy offseason for Mike Elias and the Orioles, couldn’t be a better stage-setter for the winter to come.
Put aside that he’s unquestionably talented, has been coveted by the Orioles for a while and fills a clear need in the back end of their bullpen. Factor in where Elias and the team have set expectations this winter, and signing Helsley meets what’s going to be a defining criterion.
The Orioles have signed free agent relievers before, and Helsley is unquestionably the best they’ve brought in since this front office took over. This winter, from starting pitchers to maybe another impact bat, that has to be the standard. Everything has to be a cut above their previous forays into offseason improvement, and this certainly is.
If that feels overly simple, it shouldn’t — all you need to do to understand the distinction is to think about, well, nearly every free agent signing the Orioles have made under Elias. There’s always a mitigating factor or ceiling to the type of player the club is pursuing that means they’re hardly ever, if at all, landing players at the top of the market.
I know they’ve tried to accomplish more over the years and just have not been able to get those deals done. What they’ve executed to this point is a case of getting what they paid for.
Consider the one-year infield stopgaps such as Jose Iglesias, Freddy Galvis, Rougned Odor and Adam Frazier. Think about the short-term veterans signed to the rotation over the years, including Jordan Lyles, Kyle Gibson, Tomoyuki Sugano and Charlie Morton.
Conversely, don’t think too hard about their other forays into the free agent relief market for Nate Karns, Mychal Givens or Craig Kimbrel. Those signings didn’t do much for anyone, though Andrew Kittredge proved a valuable trade chip and is likely to make an impact in 2026.
Tyler O’Neill, the only player to sign a true multiyear deal, had a miserable first year but has the chance to redeem himself.
In each case, some combination of price point, contract length and the club’s narrow view of its needs got in the way. If you feel you only have a one-year need on your infield or at the back end of the bullpen, you’re not going to be at the top of the market.
Same goes for starting pitching. The best players command the most money and years, and clubs who are giving out one-year deals often end up signing a lower level of player.
Even with Helsley having the ability to opt out of the second year of his two-year, $28 million deal after the 2026 season, we’re still talking about a significant investment in a reliever — and a very good one at that.
Ryan Helsley saved 49 games for the Cardinals in 2024, more than double his total in any other season. (Ron Jenkins/Getty Images)
He has an overwhelming fastball and a swing-and-miss slider that’s his go-to pitch. Whether it was tipping pitches or something else that made him underwhelm after his deadline deal to the New York Mets, the stuff was still there. When a reliever can do what Helsley does, it’s often more good than bad.
What’s interesting is that it seems that Helsley, who some teams were reportedly considering as a starter, signed so early with a team that expects him to pitch at the back end of the bullpen. Guys who pitch at the end of games typically don’t start for a reason; their command can be inconsistent, or they can be better in shorter spurts, or it may better suit their mentality to be on call every night rather than once or twice a week.
The best of them can handle the ninth, though, and Helsley has proven he can. Even though he’s coming off a rough couple of months, he’s closed successfully for years. The Orioles could have gotten cute in finding another temporary fill-in for Félix Bautista, who is recovering from shoulder surgery, but instead went for one of the top relievers on the market.
Sure, Edwin Diaz and Robert Suárez might get more money and years, but Helsley isn’t some discount option, even if his post-trade form might suggest so. If anything, the Orioles probably looked at some of his expected stats and chalked his numbers with the Mets up to bad luck.
Any early season hiccup is going to be scrutinized through the lens of the Orioles jumping the market on a pitcher who’d finished the prior year not at his best. But the Orioles were one of several teams vying for Helsley’s signature because he’s extremely talented and can make a difference.
Kimbrel was a fine deputy for Bautista until he wasn’t, but even from that perspective, Helsley is the best and most impactful reliever the Orioles have signed in free agency; if you expand the criteria to simply relievers they acquired in the interest of winning, he’s better than Seranthony Domínguez and Gregory Soto as well.
So, box checked in terms of this being above the level of what they’ve accomplished in the space before. That’ll be what’s required from here on out, because to accomplish what Elias wants, which is to bring a roster to spring training that the baseball world thinks can win the AL East, these are the types of moves that will make that happen.
With Helsley in the mix, no matter how good or bad the rest of their offseason business is, they’ve addressed the back of their bullpen with one of the best relievers available. That answers questions definitively. To the ones remaining, they now know the way to do it.