UPDATE: With Pete Alonso officially in the fold, the Orioles have sent a clear message that contention is no longer a distant goal. Now, fans are turning their attention to Gunnar Henderson and Jordan Westburg, wondering if franchise-defining extensions are finally within reach (J)

Orioles Mailbag: Pete Alonso, Scott Boras, Gunnar Henderson Extensions, and the Legacy of Frank Robinson

The Baltimore Orioles are entering one of the most pivotal periods in franchise history. With a young core ascending toward contention, ownership more stable than it has been in decades, and high-profile moves beginning to reshape perceptions of the organization, fans are naturally asking deeper questions — not just about wins and losses, but about philosophy, legacy, and long-term vision.

Two recent reader questions cut directly to the heart of that discussion. One focuses on whether the Orioles’ signing of Pete Alonso sends a broader message to Scott Boras regarding future extensions for cornerstone players like Gunnar Henderson and Jordan Westburg. The other explores why one of the most important figures in Orioles history — Frank Robinson — appears to receive less public recognition than his impact would suggest.

Both questions deserve careful consideration.

Does the Pete Alonso Signing Signal Anything to Scott Boras About Orioles Extensions?

From: Edward Cuneo

The Orioles’ decision to sign Pete Alonso was widely viewed as a baseball move — the acquisition of a proven right-handed power bat to address a clear lineup need. But Edward’s question goes deeper: does the signing also act as a signal to the Boras Corporation that Baltimore wants to be taken seriously when it comes time to discuss long-term extensions for its stars?

Specifically, does it send a message regarding Gunnar Henderson and Jordan Westburg, two of the most important Orioles players currently represented by Scott Boras?

The Short Answer: No, Not Directly

One signing, even a high-profile one, does not materially affect how Scott Boras approaches extension talks for his clients.

Boras is famously consistent in his methodology. He represents players, not franchises, and every negotiation is evaluated on its own merits. Whether or not the Orioles sign Pete Alonso has little bearing on how seriously Boras will consider offers for Henderson or Westburg.

If Baltimore makes a strong, market-aware proposal that aligns with a player’s value and career trajectory, Boras will listen. If it does not, he won’t — regardless of other transactions.

The Bigger Picture: Relationships Still Matter

That said, while one signing does not change negotiating dynamics, organizational credibility and relationships do matter over time.

By all indications, Orioles general manager Mike Elias and owner David Rubenstein have established a functional and professional rapport with Boras. That is meaningful.

It’s also important to note that Boras represents not just Henderson and Westburg, but also Jackson Holliday, arguably the most valuable asset in the Orioles’ system and one of the most anticipated prospects in baseball.

The Orioles and Boras are already deeply intertwined.

Extensions vs. Free Agency Reality

Historically, Boras clients are more likely to reach free agency than sign early-career extensions. That does not mean extensions are impossible, but it does mean the bar is extremely high.

For Henderson, Westburg, and Holliday, the Orioles would need to:

Demonstrate long-term financial commitment
Offer deals that reflect future MVP or All-Star ceilings
Accept risk on their end, not just cost certainty

Pete Alonso’s contract may show that Baltimore is willing to spend, but it does not fundamentally alter the leverage or strategy in Boras-led negotiations.

In short: the Alonso signing helps the Orioles’ image, but it does not move the extension needle by itself.

Why Isn’t Frank Robinson’s Legacy Promoted More by the Orioles?

From: Bruce Voelker

Bruce’s question touches on something emotional and deeply historical. Frank Robinson was instrumental in the Orioles’ success, particularly during the 1966 World Series championship season. Yet, compared to other franchise legends, his legacy feels quieter.

Why no Frank Robinson bobblehead nights?
Why no replica jersey giveaways?
Why does his name seem absent outside of a statue dedicated in 2012?

Was There Ill Will? A Falling Out? A Personality Issue?

There is no evidence to suggest that Frank Robinson was ever deliberately marginalized by the Orioles organization.

David Rubenstein spoke at length about Robinson’s importance during the Pete Alonso signing press event, clearly demonstrating respect and appreciation. That alone indicates there is no lingering resentment or discomfort from ownership.

Additionally, the Orioles held a memorial service in April 2019 following Robinson’s passing. The event included:

Brooks Robinson
Jim Palmer
Cal Ripken Jr.
Eddie Murray

Both John and Louis Angelos were in attendance, making it clear that previous ownership recognized Robinson’s contributions and legacy.

Personality vs. Perception

Frank Robinson was known as a fiercely competitive, serious, and sometimes intense figure. But there is no credible record of a “falling out” with the Orioles.

He was demanding — of himself and others — but that was part of what made him great. Many iconic leaders in baseball history shared that same edge.

It’s unlikely that personality played a significant role in how his legacy has been presented.

The Brooks Robinson Factor

One explanation may be simpler — and more human.

Frank Robinson played in Baltimore during the same era as Brooks Robinson, a universally beloved figure whose warmth, humility, and accessibility endeared him to generations of fans.

Brooks Robinson was not just admired — he was adored.

Even Frank Robinson himself admired Brooks. But when two legends share the same stage, public memory often elevates one personality more than the other.

Frank Robinson’s Orioles tenure, while historically significant, was also shorter than Brooks’. That matters when it comes to marketing, nostalgia, and generational attachment.

Not Drafted, But Transformational

It’s true that the Orioles did not draft or develop Frank Robinson. He arrived via trade from Cincinnati — a move that instantly changed the franchise’s trajectory.

Rather than diminishing his legacy, that trade should amplify it. Robinson’s impact was immediate and transformative:

1966 Triple Crown
AL MVP
World Series championship

Few players in Orioles history can claim such a direct role in a title.

Yet legacy promotion often favors longevity over impact.

Legacy Is More Than Giveaways

While Frank Robinson may not receive the same promotional treatment as others, his place in Orioles history is secure.

Statues, memorials, spoken tributes from legends, and acknowledgment from ownership carry weight — even if they are less visible than bobblehead nights.

Legacy is not always loud.

Sometimes it exists in the foundation of what a franchise became — and Frank Robinson’s influence on the Orioles is undeniable.

Final Thoughts

These two questions — one about the future, one about the past — highlight the broader evolution of the Orioles.

Baltimore is learning how to balance:

Modern player negotiations
Long-term financial vision
Historical recognition
And emotional connection with fans

The Alonso signing does not guarantee extensions for Gunnar Henderson or Jordan Westburg. And Frank Robinson’s legacy may not be promoted as loudly as some fans would like.

But both situations reflect an organization still defining who it is — and who it wants to be.

And that, perhaps, is the most important conversation of all.