🚨TENSION RISING: An insider just poured cold water on a Gunnar Henderson extension with the Baltimore Orioles — are they really willing to gamble with their franchise star over money, or is there something SERIOUSLY wrong behind the scenes? If this drags out, are the Orioles setting themselves up for a massive regret?

Gunnar Henderson Extension Unlikely? What It Means for the Orioles’ Long-Term Plans

Insider Pours Cold Water on Potential Gunnar Henderson Extension

The Baltimore Orioles have made it clear they are ready to compete now—but when it comes to locking up their young superstar Gunnar Henderson, the future may not be so straightforward.

After an aggressive offseason that included adding proven talent like Pete Alonso, Ryan Helsley, and Chris Bassitt—along with a five-year deal for Shane Baz—Baltimore signaled it is firmly in win-now mode. However, when it comes to extending Henderson, one MLB insider believes a deal is far from imminent.

Why a Gunnar Henderson Extension Looks “Extremely Low”

Insider Pours Cold Water on Potential Gunnar Henderson Extension

According to reports from insider Ken Rosenthal, the likelihood of Henderson signing a long-term extension with Baltimore in the near future is “extremely low.”

The biggest reason? Representation.

Henderson is represented by Scott Boras, one of the most powerful agents in baseball. Boras is well known for advising his clients to avoid early extensions and instead test free agency, where bidding wars can significantly increase contract value.

That strategy has historically paid off—and it makes an early deal between Henderson and the Orioles much more complicated.

The Boras Factor: Betting on the Open Market

Players represented by Boras rarely sign below-market extensions early in their careers. Instead, they typically:

Play out team control years
Maximize arbitration earnings
Enter free agency at peak value

For Henderson, that timeline is especially appealing. He still has two years of team control remaining and is projected to hit free agency at just 26 years old—a prime age that could position him for a massive contract.

Unless the Orioles offer a deal well above typical extension value (which teams rarely do), there is little incentive for Henderson to sign early.

Orioles’ Perspective: Risk vs. Reward

From Baltimore’s standpoint, the situation is tricky.

Locking up Henderson now would:

Secure a franchise cornerstone
Provide long-term roster stability
Potentially save money compared to future market value

But it would also require:

A massive financial commitment
Risk if performance declines or injuries occur

The Orioles could attempt a high-value offer—potentially in the $250 million range—but even that might not be enough to sway a Boras client away from free agency.

Henderson’s Value Continues to Rise

Insider Gives Bleak 2-Word Update on Orioles-Gunnar Henderson Contract Extension

Despite a slightly down year in 2025, Henderson remains one of the brightest young stars in MLB.

His résumé already includes:

AL Rookie of the Year (2023)
Silver Slugger Award
All-Star selection (2024)

He also showcased his talent on the international stage with Team USA in the World Baseball Classic, further boosting his profile.

At just 24 years old, Henderson still has room to improve—making his future value even more difficult to project.

Timing May Favor Waiting

Given the circumstances, the most likely scenario is that both sides wait.

For Henderson:

More time = higher potential value

For the Orioles:

More time = better evaluation of long-term worth

If Baltimore remains competitive and continues building a strong roster, they may still have an advantage when free agency arrives—but it will come at a much higher price.

Could the Orioles Pivot Instead?

If an extension truly isn’t realistic in the short term, the Orioles may shift focus to:

Extending other young players not represented by Boras
Continuing strategic free-agent signings
Maintaining financial flexibility for future negotiations

This approach allows them to stay competitive without overcommitting prematurely.

The Bigger Picture: Contending vs. Controlling Costs

Baltimore is walking a fine line between:

Building a championship-caliber roster now
Managing long-term payroll sustainability

Letting Henderson play out his contract doesn’t mean losing him—it simply means the real negotiation may come later, with much higher stakes.

Final Takeaway

MLB Insider Reveals Chances the Orioles Will Extend Gunnar Henderson

While the Orioles have shown a willingness to spend and compete, extending Gunnar Henderson appears unlikely in the near future—largely due to the influence of Scott Boras and the financial dynamics of MLB free agency.

For now, Baltimore fans can still enjoy watching their young star develop. But if current trends hold, any long-term commitment may have to wait until Henderson reaches the open market—where his value could skyrocket.