This story was excerpted from Jake Rill’s Orioles Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.
BOSTON -- It still feels a little bit surprising when the Orioles sign a player to a sizable long-term contract, right? As Baltimore fans know, the club had been reluctant to ink big deals for quite some time, so whenever that type of news is announced these days, it feels different.
It shouldn’t be surprising, though. And eventually, it shouldn’t feel so different. This appears to be just how the O’s operate in 2026 (and likely beyond).
When private equity billionaire David Rubenstein and his group purchased the Orioles in March 2024, there was plenty of cautious optimism that times could be changing. Maybe the O’s would spend more money on players. Perhaps they’d work out long-term extensions. Big-time splashes in free agency seemed more plausible.
It didn’t take long for president of baseball operations Mike Elias to express a willingness to increase payroll. It did take some time, however, for some big deals to come to fruition, as negotiations don’t often happen overnight.
But sure enough, Rubenstein, the ownership group and the front office are all putting their money where their mouths are.
So, it didn’t feel quite as surprising when Baltimore announced a five-year extension for right-hander Kyle Bradish on Saturday. The long-term deal (which is worth $90 million, per sources) is one of multiple the O’s have put together recently.
Only two players have signed larger contracts than Bradish in franchise history -- Chris Davis (seven years, $161 million in January 2016) and Pete Alonso (five years, $155 million in December 2025).
Since last Aug. 22, the Orioles have signed four of the seven largest contracts in team history, inking long-term commitments to Alonso, Bradish, right-hander Shane Baz (five years, $68 million) and catcher Samuel Basallo (eight years, $67 million).
“Keeping players of Kyle’s caliber in an Orioles uniform is an important part of our long-term vision,” Rubenstein said in a statement on Saturday.
That had already been made clear by the organization’s actions over the past 11 months.
Now, here’s a question: Who’s next?
Any time Baltimore signs someone to a big contract, it’s a positive move for clubhouse morale. Players see the club is willing to invest in the future, and it shows them it’s possible they could eventually ink a sizable deal of their own.
Bradish is now the highest-paid pitcher in Orioles history, and his teammates are thrilled.
“I was very happy for him,” left-hander Trevor Rogers said over the weekend in Houston. “He got locked up, and his soon-to-be family and his family’s family, he’s set for life. That’s the biggest thing in this game. The fact that he gets to wear that uniform for a long time, it’s awesome. Really happy for him and [his wife] Mollie, and that’s what you work toward in this game, and he did it. Couldn’t happen to a better guy.”
Maybe it will happen next to Rogers. The 28-year-old southpaw is set to hit free agency after the season, but has shown his worth to Baltimore, winning the 2025 Most Valuable Oriole Award and recording a 1.69 ERA over eight starts since the beginning of June.
The list of potential extension candidates is long and should also include three-time All-Star catcher Adley Rutschman, star shortstop Gunnar Henderson and perhaps outfielder Colton Cowser or infielder Jackson Holliday. There’s a lot of young talent in the O’s core -- players the organization would like to continue to build around.
After all, Elias already said earlier this summer that he hopes Rutschman could be “here forever.”
“We want to win with him here,” Elias said of Rutschman in late June. “He’s been the cornerstone basically since I’ve been here. He’s an enormous part of it. I wish our commitment was greater than it is.”
And maybe it will be. The Orioles are willing to negotiate and finalize extensions at this point, so any of these players could be next to sign a long-term contract.
It shouldn’t be a surprise if (and potentially when) it happens.