Baltimore Orioles Should Prioritize Long-Term Extension for Gunnar Henderson

With the announcement earlier this week that Athletics shortstop Jacob Wilson has signed a seven-year contract extension, renewed attention has turned toward the Baltimore Orioles and their long-term plans for their own franchise shortstop, Gunnar Henderson. Wilson’s deal may not directly impact Baltimore, but it serves as a timely reminder of how quickly the market for elite young position players can shift — and how costly inaction can become.

Across Major League Baseball, superstar-caliber position players approaching free agency are becoming increasingly rare. Teams are locking up their elite talent earlier than ever, often before arbitration years are complete. Gunnar Henderson stands out as one of the few true franchise-level position players who is not yet tied down beyond team control.

While there is no immediate danger of Henderson leaving Baltimore, the Orioles may benefit from proactively pursuing a long-term extension sooner rather than later — one that mirrors the type of commitment Oakland just made to Wilson.

Gunnar Henderson Is Not Going Anywhere — For Now

To be clear, there is no urgency in the traditional sense. Henderson has only recently entered arbitration and remains under Orioles team control through at least the 2028 season. Baltimore has no incentive to trade him, and Henderson has every reason to remain where he is. Barring injury or unforeseen circumstances, he will be an Oriole for the next three seasons.

However, the absence of immediate pressure does not mean the Orioles should delay action. In fact, history suggests that waiting too long to negotiate with elite players often leads to higher costs, tougher negotiations, and increased risk of losing generational talent in free agency.

Henderson represents the type of player franchises build around for a decade or more. If Baltimore truly intends to sustain contention rather than peak briefly, securing Henderson long term should be a top organizational priority.

Henderson’s Proven Superstar Profile

Despite a down year for the Orioles overall in 2025, Gunnar Henderson has fully lived up to his billing as one of baseball’s brightest young stars.

In 2024, Henderson put together a sensational All-Star campaign. He posted a .281 batting average, drew 78 walks, hit 37 home runs, stole 21 bases, and provided strong defense at shortstop. That all-around performance earned him a fourth-place finish in the American League MVP voting and firmly established him among the game’s elite.

While his power numbers dipped slightly in 2025, Henderson remained an impact player. He finished the season with a 121 OPS+ (ERA+ equivalent for hitters), reached the 500-hit milestone for his career, and did so while still just 24 years old. Even during a relative “down” season, Henderson performed well above league average — a hallmark of true star talent.

At this stage of his career, Henderson is no longer merely a top prospect or promising young player. He is a franchise cornerstone entering his prime.

The Risk of Long-Term Deals — and Why It’s Worth It

Every long-term extension carries risk, even when the player involved appears to be a sure thing. Baseball history is littered with examples of deals that looked brilliant at signing and disastrous in hindsight.

One of the most prominent recent cases is Wander Franco. The Tampa Bay Rays locked Franco into a massive 10-year extension early in his career, only to see his time in MLB effectively end less than two years later due to off-field issues. That situation underscores the inherent uncertainty of long-term commitments.

That said, there is no indication — on or off the field — that Gunnar Henderson carries similar risk. His professionalism, performance consistency, and steady development suggest the probability of catastrophic failure is extremely low.

More importantly, the risk of underperformance appears minimal. Henderson has already proven himself across multiple MLB seasons, against elite competition, and in high-leverage situations. If anything, the greater risk lies in allowing him to reach free agency unencumbered.

The Real Threat: Free Agency After 2028

The most significant risk facing the Orioles is not Henderson declining — it is Henderson leaving.

Once Henderson reaches free agency after the 2028 season, Baltimore would be forced to compete financially with baseball’s biggest spenders. Teams like the New York Mets, Los Angeles Dodgers, and New York Yankees routinely position themselves to strike when elite talent hits the open market.

As just one example, the Mets are projected to have substantial financial flexibility when Henderson becomes a free agent, with contracts for players like Marcus Semien and Bo Bichette coming off the books around the same time. In that scenario, Baltimore could find itself outbid regardless of its willingness to spend.

A long-term extension eliminates that uncertainty entirely, allowing the Orioles to lock in cost certainty and retain a face-of-the-franchise player through his prime years.

Orioles Have Demonstrated Willingness to Spend

One of the most compelling arguments in favor of a Henderson extension is that the Orioles now have both the means and the mindset to make it happen.

This past winter, Baltimore shattered previous perceptions by signing first baseman Pete Alonso to a five-year, $155 million deal. The move signaled a clear shift in organizational philosophy — from cautious rebuilding to aggressive contention.

In addition to the Alonso signing, the Orioles bolstered the roster through trades, acquiring Taylor Ward and Shane Baz using prospect capital. They have also been linked to high-end free agents such as pitcher Framber Valdez, further indicating a willingness to leverage increased revenues to push toward sustained playoff success.

In short, Baltimore is no longer operating like a small-market team content to develop talent and let it walk. The infrastructure and financial flexibility are now in place.

Scott Boras Factor Could Work in Baltimore’s Favor

Another subtle but important element is Henderson’s representation. Like Pete Alonso, Gunnar Henderson is a client of super-agent Scott Boras.

Boras is known for maximizing player value, but he is also keenly aware of organizational relationships. While signing Alonso was not done solely to curry favor with Boras, maintaining a positive working relationship with one of the most powerful agents in sports can only help facilitate future negotiations.

Extensions involving Boras clients are notoriously difficult, but not impossible — especially when the player believes in the organization’s direction and competitive future.

Baltimore’s recent spending spree sends exactly the kind of message Boras clients want to see.

Henderson vs. the Future Free-Agent Market

Looking ahead, the future free-agent market for elite position players is remarkably thin. Aside from Henderson, the only comparable young superstar projected to reach free agency in the coming years is Cincinnati Reds phenom Elly De La Cruz.

While De La Cruz reportedly turned down a nine-figure extension offer from the Reds, there is little indication Henderson would take the same stance. His situation differs in several key ways, including organizational stability, market growth, and competitive trajectory.

That scarcity only increases Henderson’s eventual market value — another reason the Orioles should act early rather than later.

Final Verdict: Time for the Orioles to Act

The Baltimore Orioles have every reason to pursue a long-term extension for Gunnar Henderson. They have the financial resources, the competitive ambition, and the organizational momentum to make it happen.

Waiting may feel safe given Henderson’s remaining years of team control, but history suggests that hesitation often leads to regret. Locking Henderson up now would protect the Orioles from future bidding wars, stabilize the franchise’s core, and send a powerful message to fans and players alike.

Gunnar Henderson is not just a star — he is one of the few true franchise-level position players in baseball today. For Baltimore, securing his future should not be a question of “if,” but “when.”