Now that the Orioles’ new management group has done its first extension and sees all the positive vibes around the Samuel Basallo signing, the question immediately becomes who’s next?
Well, let’s get real. David Rubenstein would love to do the same with Gunnar Henderson, Jackson Holliday and Jordan Westburg. There is one small problem. Actually, it’s a big problem — Scott Boras is the agent for those three important players. I’ll never say never, except when it comes to early extensions that don’t necessarily maximize the earning potential of Boras clients.
Félix Bautista would have been a perfect fit for a nice three-year deal that would have covered Bautista’s final two arbitration years and one free-agent year. That would have guaranteed his family riches beyond their wildest dreams. At 30 years of age and facing his second very serious injury, it’s hard to imagine Bautista ever getting a mountain of life-altering money now.
Colton Cowser is a great kid and is not represented by Boras, but he has failed to live up to his No. 1 draft pick status.
A three-year deal with Dean Kremer would make some sense to me. It would cover his final two arbitration years and one free-agent year, perhaps guaranteeing him in the neighborhood of $20 million. It would pay Kremer well but leave him another bite at the apple if he takes his game to another level.
But the most obvious gambit Orioles GM Mike Elias has to explore and execute is with Trevor Rogers. Rogers’ victory against the Astros on Aug. 24 was his 11th consecutive start allowing two runs or fewer, passing Milt Pappas, who did that 10 times.
Additionally, Rogers ERA of 1.40 in his first 13 starts of the season is the best stretch in club history, even better than Hoyt Wilhelm (1.50 ERA in 1959) and Jim Palmer (1.55 ERA in 1975).
So the question isn’t about whether the Orioles want Rogers here long term. The question really reverts back to Rogers. How much is enough to keep him here without the club possibly getting burned down the line?
The Orioles control Rogers for one more season and then he is eligible for free agency. The lefty will turn 28 in November. He is making $2.6 million in 2025. The $3.4 million he signed for as a first-round pick of the Marlins back in 2017 is still the most he’s made at any point in pro ball.
Here is the very tough question for Rogers to discuss with his family and agent. If he turns down an extension and has a big season in 2026, he is probably in line for a significant free-agent deal. Here’s a look at what top left-handed starters have signed for recently:
Max Fried: eight years, $218 million with the Yankees in free agency
Blake Snell: five years, $182 million with the Dodgers in free agency
Garrett Crochet: six years, $170 million with the Red Sox, covering one arbitration year and five free-agent years
Carlos Rodón: six years, $162 million with the Yankees in free agency
Robbie Ray: five years, $115 million with the Mariners in free agency, later traded to the Giants
Eduardo Rodríguez: four years, $80 million with the Diamondbacks in free agency
Sean Manaea: three years, $75 million with the Mets in free agency
Yusei Kikuchi: three years, $64 million with the Angels in free agency
Tyler Anderson: three years, $39 million with the Angels in free agency
However, two things stand in the way of that outcome. He could simply revert back to the struggling major league starter he was for much of his time in Miami, at which point big money becomes a pipe dream. An injury could also ruin any chance for a successful 2026.
So, where is the sweet spot for Rogers to do the smart thing? I think the Orioles can blow past his projected arbitration number for 2026 and come up with this kind of structure:
2026: $8 million
2027: $10 million
2028: $12 million
2029: $15 million club option with a $3 million buyout
That’s a $33 million guarantee with a chance to grow to $45 million, covering his age 28-31 seasons. Makes sense to me. Will David Rubenstein and Mike Elias offer that deal and will Trevor Rogers do the smart thing?
See Also:
• Stan ‘The Fan’ Charles: Could Adley Rutschman Be The Big Trade Piece For Orioles?
• Orioles LHP Trevor Rogers On Regaining Top Form, Unusual Key To Success
Photo Credit: Kenya Allen/PressBox