The New Era of Shortstop Contracts

With the recent announcement that Athletics shortstop Jacob Wilson has signed a long-term extension, binding him to the franchise for the next seven years, attention has shifted back to the Baltimore Orioles and their situation with their own shortstop star, Gunnar Henderson. This development highlights the importance of securing top-tier talent through long-term deals, especially in a landscape where superstar-caliber position players are scarce in the near future.

Henderson is one of the few standout players set to enter free agency in the coming years. While there’s no immediate indication that he will leave, his current contract keeps him under team control until at least 2028. Given the Orioles’ willingness to spend this summer, it might be prudent for them to consider a deal similar to Wilson’s, just in case.

Henderson’s Proven Star Quality

Despite a relatively down year in 2024 due to a poor season for the Orioles as a whole, Henderson has shown that he is as good as advertised. In that season, he hit a .281 batting average, recorded 78 walks, 37 home runs, and 21 steals. His performance earned him an All-Star selection and a fourth-place finish in the American League Most Valuable Player vote. Even though his power production dipped in 2025, he still managed a 121 ERA+ campaign and reached the 500-hit milestone in his career, all while being only 24 years old.

Henderson is a franchise-level prospect, and his consistent performance over his first three-and-a-half MLB seasons suggests that he is unlikely to underperform in a long-term contract. However, there are risks involved in any such deal. For instance, the Tampa Bay Rays faced a setback when Wander Franco’s career was cut short due to off-field issues, despite being locked into a ten-year deal. While there’s no reason to believe anything negative will happen to Henderson, it’s important to acknowledge the potential for unforeseen circumstances.

The Orioles Have the Money

The Orioles have shown a willingness to invest in their roster this winter. They signed first baseman Pete Alonso to a five-year, $155 million deal, and made trades for Taylor Ward and Shane Baz. There are also rumors that they are interested in acquiring Framber Valdez, a free agent pitcher, using their improved revenues to build a competitive team alongside their drafted core.

Alonso is represented by Scott Boras, the same agent who represents Henderson. Building a strong relationship with Boras could help facilitate a deal for Henderson. While signing Alonso was not primarily done to please Boras, it could serve as a positive by-product of the relationship.

The Future Market for Star Players

The Orioles have the incentive, money, and relationships to secure a long-term deal with Henderson. As they look to the future, they will find that Henderson and Elly De La Cruz of the Cincinnati Reds are the only two star-quality position players on the market. Although De La Cruz turned down a nine-figure extension from the Reds, there seems little reason to believe Henderson would do the same.

In conclusion, the Orioles have the opportunity to lock in one of the few remaining franchise stars before he hits free agency. With the right approach, they could ensure that Henderson remains a key part of their future.