Baltimore Orioles fans have been eagerly awaiting a long-term commitment to Gunnar Henderson, a player who has consistently proven his worth. Since winning the AL Rookie of the Year Award in 2023 and making his All-Star debut in 2024, Henderson has continued to shine, even posting a 121 OPS+ and 5.3 bWAR in a so-called down year in 2025. His talent places him among the league's elite shortstops, right up there with Bobby Witt Jr.
Witt, who secured a massive deal with the Kansas City Royals, set a precedent with his 11-year, $288.7 million contract. Considering the market's inflation since then, any negotiations for Henderson are likely to start at a similar figure, especially when Witt's deal could escalate to over $370 million.
Yet, financial considerations are just one part of the puzzle. Baltimore not only needs to meet these steep salary demands but also navigate negotiations with Scott Boras, Henderson's agent. Boras, known for taking his clients through arbitration and onto free agency, employs a strategy that often frustrates fans but certainly benefits his clients.
There's a glimmer of hope, though, as Boras recently secured a long-term extension for Milwaukee Brewers prospect Cooper Pratt. Despite not having played a Major League game yet, Pratt signed an eight-year, $50.75 million deal, with additional club options. This move suggests that Boras might be open to early extensions under the right circumstances.
Pratt joins a select group of Boras clients who have agreed to long-term deals before free agency, including stars like Xander Bogaerts, Jose Altuve, and Stephen Strasburg. For the Orioles, this could mean that if they are willing to offer Henderson a deal reflecting his market value, there might be room for negotiation.
Baltimore is beyond the stage of offering a bargain akin to Pratt's deal. If they aim to keep Henderson, they must be prepared to match or exceed the high-end offers seen in the league. Pratt's contract serves as a reminder that while Boras is a tough negotiator, he isn't entirely immovable.