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BALTIMORE, MARYLAND – AUGUST 21: Gunnar Henderson #2 of the Baltimore Orioles throws the ball during warm up before playing against the Houston Astros at Oriole Park at Camden Yards on August 21, 2025 in Baltimore, Maryland. (Photo by Patrick Smith/Getty Images)
With the announcement earlier this week that Athletics shortstop-for-now Jacob Wilson has signed a long-term extension that binds him to the franchise for the next seven years, scrutiny returns to the Baltimore Orioles, and their situation with their own shortstop star.
A cursory look around the MLB finds scant few superstar-caliber position players across the whole of baseball who are set to enter free agency in the near future. Gunnar Henderson is one of the few.
This is not to say that any departure is imminent. Henderson has only just entered arbitration, and is under Orioles team control until at least 2028, if they want him to be. With absolutely no incentive to deal him in trade, Henderson will be an Oriole for the next three years, barring disaster. But perhaps the franchise that has shown a willingness to spend this summer should greater prioritize getting a Wilson-esque deal, just in case.
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Henderson’s Proven Star Quality
Despite a relatively down year last season amid a poor campaign for the Orioles as a whole, Henderson has become as good as advertised. In 2024, he hit for a .281 batting batting average to go along with 78 walks, 37 home runs, 21 steals and decent defense during an All-Star season in which he finished fourth in the American League Most Valuable Player vote. And although a slump in his power production would follow in 2025, he would still go on to produce a 121 ERA+ campaign and hit the 500-hit milestone for his career, all while still aged only 24. He is a franchise-level prospect.
There is, of course, risk to any deal. By way of example, although he was locked up to an extension far earlier in his career than Henderson could now be, the Tampa Bay Rays found this out when their supposed sure-fire shortstop prospect Wander Franco found his career truncated merely a year and a half into his ten-year deal due to his off-the-field scandal. There is no reason to assume anything nefarious is or will ever go on with Henderson, of course; this is merely to say that any long-term deal, even for the supposed franchise talents, comes with the risk of catastrophe.
The risk of such catastrophe is negligible, and the risk of contract underperformance seems similarly improbably given Henderson’s proven qualities over his first three-and-a-half MLB seasons. The real risk, though, is that of Henderson walking after 2028. After all, to use just one example, the New York Mets are currently positioned so that both Bo Bichette (recently plucked from the World Series-winning Toronto Blue Jays) and Marcus Semien will be coming off the books at the same time that Henderson hits the market. An extension removes this risk.
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Orioles Have The Money
The Orioles opened up the purse strings this winter when they signed first baseman Pete Alonso, formerly of the New York Mets, to a five-year, $155 million deal, and made trades for Taylor Ward and Shane Baz from their prospects pile. It is also hoped that they are still not done, with the team being linked to a big-money move for free agent pitcher Framber Valdez, using their improved revenues to spend their way into contention alongside the drafted core.
Alonso is a client of power agent Scott Boras. So is Henderson. Fostering a good relationship with Boras, then, might help to bring a Henderson deal closer to fruition. As much as the business of top-level professional sport is about uncountable riches, those riches are also swayed by relationships, such is the frailty of the human condition. Signing Alonso would not primarily have been done to keep Boras sweet, of course – but it could certainly be a positive by-product of it.
All in all, the Orioles have the incentive, money and relationships to tie down one of the few star-quality position players not currently tied down. Those eyeing up the future market will see only Henderson and Elly De La Cruz of the Cincinnati Reds on it. And although Elly turned down nine figures in an extension from the Reds, there seems little reason for Henderson to do the same.
Mark Deeks I am continuously intrigued by the esoterica and minutiae of all the aspects of building a basketball team. I want to understand how to build the best basketball teams possible. No, I don’t know why, either. More about Mark Deeks
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