The start of the 2026 MLB season could not be going much better for the Baltimore Orioles. They beat the Minnesota Twins on Opening Day (BAL 2, MIN 1) thanks to seven shutout innings from lefty Trevor Rogers, who showed last year’s success was no fluke. a day later the O’s locked up right-hander Shane Baz to a five-year extension worth $68 million. The deal buys out two free-agent years.
“As soon as they reached out, I knew that we wanted to get something done,” Baz said during Saturday’s press conference, adding it was a “no-brainer” to sign long-term. “It’s just such a great place to be. I was probably a little bit surprised about it, but it was just too good of an opportunity.”
Baz is the second cornerstone player the O’s have signed long-term in the last eight months, joining catcher (and top prospect) Samuel Basallo. Basallo inked an eight-year deal worth $67 million last August. It stands to reason the Orioles will try to lock up more players soon, and if nothing else, franchise shortstop Gunnar Henderson is at least open to a long-term deal with Baltimore.
“Any time they want to come my way, I’m open ears,” Henderson told the Baltimore Banner on Saturday. “But also my first priority right now is to win ballgames and do whatever I can to bring a championship to the Orioles. All of that stuff is secondary right now”
Henderson, 24, is three years away from free agency and also the one homegrown O’s hitter who’s broken through and become a true star. Adley Rutschman has backslid the last season-and-a-half and others like Colton Cowser, Jackson Holliday, Heston Kjerstad, and Coby Mayo have not taken that big leap forward yet, if not stalled out. (To be fair, Holliday is still so young.)
Few players of Henderson’s caliber have signed long-term extensions at the same service time level. Here, listed by guaranteed dollars, are the largest contracts given to position players three years away from free agency:
The Orioles would give Henderson the Raleigh contract in a heartbeat, I’m sure, but that’s not going to happen. As good as Raleigh is, he was four years older than Henderson is right now when he signed that contract, and the catcher aging curve is brutal. The wear and tear of the position was baked into the contract. That won’t be the case with Henderson.
Also, Henderson is a Scott Boras client, and Boras likes to take his top clients into free agency. It’s not universal — several top Boras clients have passed up free agency for extensions — but it’s uncommon. The Orioles will likely have to pay top-of-the-market dollars to get Boras and Henderson to pass up hitting free agency at ripe earning age of 27 in a few years.
For argument’s sake, let’s spitball a Henderson extension from scratch since there aren’t any good benchmarks around the league. How does this sound?
- 2026: $8.5 million (his salary this year)
- 2027: $15 million (second arbitration year)
- 2028: $20 million (third arbitration year)
- 2029-39: $35 million annually (free agent years)
That adds up to 13 years and $420 million spanning 2027-39. The $35 million annual salary from 2029-39 is Vladimir Guerrero Jr./Corey Seager money, not Juan Soto money, which is where the discount comes in. Also, that deal would tie Henderson to the O’s through his age-38 season. Guerrero, Soto, and a few other superstars are signed through their age-40 seasons.
A $420 million deal would be the fifth-largest contract in history and you could easily bump that over Mike Trout’s $426.5 million contract with a signing bonus and/or an option buyout. Henderson won’t be as young as Guerrero or Soto when he hits free agency, nor is he the singular Shohei Ohtani. The fourth-richest contract ever might be what it takes to convince Boras/Henderson to sign now.
The longer the O’s wait to extend Henderson, the less likely an extension becomes. He’ll be that much closer to free agency, and he will have also made some good money through arbitration, making it less of a gamble to bet on himself. The upcoming free agent markets are thin. Henderson, in three years, will be the best position player free agent since Soto last year, and not by a little.
More extensions could be coming for the Orioles — “We are open for business, of course,” owner David Rubenstein said at Baz’s press conference Saturday — though chances are one won’t happen with Henderson because of the Boras factor and the money we’re talking about here. Rogers, maybe Rutschman, and a few others are more realistic extension candidates.