The Baltimore Orioles are off to a dream start in the 2026 MLB season—but if they want to secure their brightest star for the long term, the real challenge is only just beginning. Locking up Gunnar Henderson could require one of the largest contracts in baseball history, and the clock is already ticking.

Orioles Building Momentum Early in 2026

Baltimore opened the season on a high note with a win over the Minnesota Twins on Opening Day, powered by a dominant performance from Trevor Rogers. That momentum carried into the front office, where the Orioles quickly secured right-hander Shane Baz on a five-year, $68 million extension—buying out two of his free-agent years.

This move follows another major commitment made just months earlier, when top prospect Samuel Basallo signed an eight-year, $67 million deal. The message is clear: Baltimore is serious about building a sustainable core.

But while those deals are significant, they pale in comparison to what it will take to keep Gunnar Henderson in an Orioles uniform long-term.

Gunnar Henderson: The Franchise Cornerstone

At just 24 years old, Henderson has already emerged as the face of the franchise. Among Baltimore’s homegrown hitters, he’s the one who has truly broken through into superstardom. While players like Adley Rutschman, Colton Cowser, Jackson Holliday, Heston Kjerstad, and Coby Mayo continue to develop, none have matched Henderson’s consistency and impact at the big-league level.

Importantly, Henderson has made it known he’s at least open to staying in Baltimore.

“Any time they want to come my way, I’m open ears,” Henderson said—while emphasizing that his current focus remains on winning.

That openness gives the Orioles a window—but it’s a narrow one.

The Scott Boras Factor

One of the biggest complications in any potential extension is Henderson’s representation by Scott Boras. Boras is famously known for guiding elite clients to free agency, where bidding wars often drive contracts to historic levels.

While exceptions exist, they are rare. For Baltimore to convince Henderson to sign early—three years before free agency—they will likely need to offer a deal that reflects full market value, if not more.

And that’s where things get expensive.

Why There’s No Clear Contract Blueprint

There are very few precedents for players of Henderson’s age and caliber signing long-term extensions this early. Comparable deals—like those signed by Austin Riley or Cal Raleigh—don’t quite apply.

Riley’s 10-year, $212 million deal and Raleigh’s six-year, $105 million extension were both significant, but neither player matched Henderson’s combination of youth, positional value, and upside at the time of signing. Raleigh, in particular, was older and plays catcher—a position with a much harsher aging curve.

That means the Orioles are essentially negotiating in uncharted territory.

A $400M+ Deal Might Be the Starting Point

To realistically keep Henderson off the open market, Baltimore may need to structure a deal in the range of 13 years and $400–$420 million.

A hypothetical framework could look like this:

• Gradual salary increases through arbitration years
• Followed by ~$35 million annually across free-agent seasons

This type of contract would align Henderson with stars like Corey Seager and Vladimir Guerrero Jr. in terms of annual value—while still falling short of the top-tier megadeals commanded by players like Juan Soto or Shohei Ohtani.

Even then, it might not be enough.

A deal in the $420 million range would rank among the five largest contracts in MLB history—approaching or even surpassing the $426.5 million contract signed by Mike Trout.

Timing Is Everything

If there’s one thing working against the Orioles, it’s time.

The longer Baltimore waits, the stronger Henderson’s position becomes. As he moves closer to free agency:

• He earns more through arbitration
• He reduces the financial risk of waiting
• And he enters a potentially weak free-agent market

That last point is crucial. When Henderson hits free agency—potentially at age 27—he could be the most sought-after position player available in years.

That kind of leverage is exactly what Boras thrives on.

Orioles’ Strategy Moving Forward

Team owner David Rubenstein has already signaled that the organization is willing to spend, stating, “We are open for business.” That’s encouraging for fans—but committing $400+ million to a single player is a different level of investment entirely.

More extensions could still be on the horizon. Players like Rogers or even Rutschman may be more realistic candidates for near-term deals. But Henderson represents a unique case—one that requires both financial boldness and perfect timing.

Final Outlook

For the Baltimore Orioles, the situation is simple but daunting: if they truly want Gunnar Henderson to be the face of the franchise for the next decade, they must be prepared to pay like it.

That means thinking beyond traditional extensions and embracing the reality of modern baseball economics—where elite young stars command historic deals.

Because if Baltimore hesitates, the outcome is predictable. Henderson will hit free agency, and when he does, the entire league will be ready to pay whatever it takes.

And at that point, keeping him won’t just be difficult—it might be impossible.