The Orioles' relationship with their star shortstop, Gunnar Henderson, has been a topic of intrigue ever since they made an extension offer during last year's Spring Training. While that offer wasn't accepted, it's unclear if any talks have resumed this year. With Scott Boras as Henderson's agent, the odds of reaching an agreement seem slim, as Boras typically prefers his clients to test the waters of free agency.
Henderson is currently entering his first year of arbitration and is set to become a free agent after the 2028 season, when he'll be just 27. Given his age and impressive stats over four big league seasons, Henderson and Boras might be eyeing a record-breaking contract. This could potentially push the Orioles out of their comfort zone financially.
However, Baltimore has shown a willingness to invest under the ownership of David Rubenstein, who took over in early 2024. The eight-year, $67 million deal with Samuel Basallo last August marked a significant shift for the franchise, which hadn't secured a long-term extension in over a decade. Moreover, their recent five-year, $155 million contract with Pete Alonso, another Boras client, stands as the second-largest in team history.
Extending Henderson could demand a contract three times the size of Alonso's, especially if Boras aims to set new market standards. Henderson's performance dipped slightly in 2025 due to injuries, posting a .274/.349/.438 line with 17 homers and 30 steals.
Despite these challenges, he still delivered a solid 120 wRC+ and 4.8 fWAR. With a return to full health, Henderson might replicate his 2024 form, where he smashed 37 homers with a .281/.364/.529 slash line.
The Orioles might be waiting to see Henderson back at his best before committing to such a substantial investment. Currently, Alonso and Basallo are the only major long-term contracts on their books, so a landmark deal for Henderson isn't off the table if they view him as their cornerstone.
However, as noted by insiders, the more likely scenario is that an extension doesn't materialize. This could lead to Henderson testing free agency or Baltimore possibly trading him during the 2027-28 offseason to maximize their return.