Ryan Helsley Joins the Orioles, Brandon Hyde Heads to the Rays, and a Look Back at Key O’s December Deals
The Orioles made it official: Ryan Helsley is the newest addition to Baltimore’s bullpen. The right-hander signed a two-year, $28 million deal, which includes an opt-out after the first season-giving both sides some flexibility depending on how 2026 shakes out.
Helsley brings high-leverage experience and a power arm to a bullpen that’s looking to solidify its late-inning options. While he’s had stretches of dominance, the key for Baltimore will be keeping him healthy and consistent. If he delivers the kind of electric stuff he’s shown in the past, this could be a major win for the O’s.
Meanwhile, Helsley’s departure didn’t leave a hole for long. His former club, the Mets, reportedly filled that spot by signing Devin Williams to a three-year deal.
Williams, coming off a quiet stint with the Yankees, now gets a fresh start in Queens. His arrival could be a signal that Edwin Díaz’s time in New York is winding down.
If Díaz does move on, the Orioles will be hoping he doesn’t land within the AL East. The last thing Baltimore needs is another elite arm in the division.
Brandon Hyde Finds a New Role-Back in the AL East
Former Orioles skipper Brandon Hyde is back in baseball. The Tampa Bay Rays announced they’ve hired him as a senior advisor for baseball operations. After interviewing for a handful of managerial vacancies this offseason and coming up short, Hyde finds himself in a front-office role with one of the savviest organizations in the league.
Hyde’s time in Baltimore came to an end back in May after a rocky start to the 2025 season, but his legacy with the club is more than just a rough exit. He weathered the storm during the Orioles’ rebuild, managing through some lean years with rosters that were clearly focused on the future. His efforts paid off in 2023, when he led the team to 101 wins and earned AL Manager of the Year honors.
That season wasn’t just a blip-it was a culmination of years of guiding young talent, setting a culture, and helping shape the team’s identity. While things unraveled in 2025, Hyde’s impact on the Orioles’ current core shouldn’t be overlooked.
Now he joins a Rays organization known for maximizing talent and thinking outside the box. It’s a good landing spot for a baseball mind who still has plenty to offer-just as long as he doesn’t help Tampa take too many games off the O’s.
Orioles Birthdays and a Trip Through December 2 History
A couple of 2025 Orioles are celebrating birthdays today-catcher Gary Sánchez turns 33, and reliever Bryan Baker hits 31. Neither is expected back in Baltimore next season.
Baker spent nearly his entire big-league career with the Orioles, appearing in 173 games over four seasons and posting a solid 3.73 ERA. He was dealt to the Rays this past July in exchange for a draft pick that turned into Slater de Brun.
Sánchez, meanwhile, had a brief and injury-plagued stint in Baltimore, playing just 29 games due to wrist and knee issues. He’s now a free agent.
December 2 has historically been an active day for Orioles transactions, and it’s delivered some memorable moments-both good and not-so-good.
Frank Robinson Trade (1971): This one still stings. On this date in 1971, the Orioles traded Hall of Famer Frank Robinson to the Dodgers after six iconic seasons in Baltimore.
Robinson’s numbers as an Oriole were legendary: a .300 average, .401 OBP, .543 slugging, 179 home runs, and 545 RBIs. He won the Triple Crown and AL MVP in 1966, leading the Orioles to their first World Series title.
The return? Doyle Alexander and a few depth pieces.
That deal remains one of the most debated in franchise history.
Bobby Ávila Acquisition (1958): The Orioles picked up former batting champ Bobby Ávila from Cleveland. He was a three-time All-Star and a staple of the Indians’ infield for a decade, but his time in Baltimore was brief-just 20 games, hitting .170 before being lost on waivers.
Harold Baines Returns (1993): Maryland native and future Hall of Famer Harold Baines re-signed with the O’s on this date after OPS’ing .900 in his first season with the club. Baines would go on to play six more seasons for Baltimore across three stints, batting .301/.379/.502 with 107 home runs. He was a steady, professional hitter who gave the Birds a reliable presence in the middle of the order.
Jim Johnson Trade (2013): After back-to-back 50-save seasons, closer Jim Johnson was shipped to Oakland in a cost-cutting move. The Orioles weren’t willing to pay the arbitration raise, and while the trade was unpopular at the time, it turned out to be a savvy decision.
Johnson struggled badly in 2014, posting a 7.09 ERA across two teams. He eventually found his footing again, but his elite closer days were behind him.
Mark Trumbo Deal (2015): This one was a rollercoaster. The Orioles acquired slugger Mark Trumbo from the Mariners, and he immediately made an impact-leading the league with 47 home runs in 2016 and earning an All-Star nod.
That power surge helped Baltimore secure a Wild Card berth. But the follow-up wasn’t as sweet.
The O’s re-signed Trumbo to a three-year deal, and he never regained that 2016 form, finishing the contract with a -0.3 WAR before retiring after an injury-shortened 2019 season.
Looking Ahead
The Orioles have been aggressive this offseason, and the Helsley signing is just the latest move that signals a win-now mindset. With the Winter Meetings on the horizon, it wouldn’t be a shock to see more moves coming. December 2 has already been a busy day in franchise history-don’t be surprised if they add another chapter before the day is done.