Red Sox Top 20: The Most Important People in 2026

The Boston Red Sox are stepping into a new chapter with plenty of hope, some nagging questions, and a roster that could win big—if things fall into place. Let’s take a look at the key people shaping this franchise as 2026 approaches, from star players and front-office brains to ownership’s long-term plans and the tricky financial situation they’re juggling.

Garrett Crochet: The Red Sox’s Most Important Player

Every contender needs an ace. For Boston, that’s Garrett Crochet. Signed through 2031, Crochet doesn’t just steady the rotation—he sets the tone for it.

He’s got real Cy Young–level talent, giving Boston the kind of top starter they’ve missed since Chris Sale’s best days. His health and performance shape every pitching move the team makes.

If the rotation is centered on Crochet and he stays healthy, Boston could go deep into October. Of course, that depends on the rest of the staff holding up, too.

Why Crochet Is the Linchpin

If Crochet pitches like a true ace, the Red Sox can manage workloads, protect their young arms, and attack the postseason with confidence. If he struggles, suddenly everything else feels a lot tougher.

Anthony’s Emergence Changes the Equation

Masataka Yoshida still matters, but Anthony has become the real No. 2 cornerstone. He’s signed through 2033 and was hitting .323 with an .859 OPS before an oblique injury ended his season early.

Stats only show so much. When Anthony played, Boston looked sharper—more dynamic, more disciplined, and just plain better.

A Lineup Catalyst

Anthony’s contact skills and awareness at the plate make him a lineup anchor for the future. Boston needs that as they try to find more consistency on offense.

Ownership Under the Microscope

John Henry, Tom Werner, and Sam Kennedy are under the spotlight from fans. Since 2019, results have bounced around, and people wonder if their focus is split between baseball and business.

The front office says they’re still chasing championships, but after all, actions in free agency will prove more than any press conference ever could.

The Trust Gap

With a $243.4 million projected luxury-tax payroll for 2026—just a shade below the $244 million line—ownership seems to be threading the needle again instead of going all-in.

Craig Breslow and the Search for Stability

Chief baseball officer Craig Breslow heads into year three having brought calm to a previously rocky organization. He’s rebuilt the pitching pipeline, locked up key players, and restored some much-needed confidence inside the club.

Process vs. Results

Breslow’s decisions have mostly inspired trust, but let’s be honest—patience won’t last forever if the wins don’t come soon.

Veteran Arms and Bullpen Importance

Boston’s pitching depth leans on veterans like Sonny Gray and Aroldis Chapman. The bullpen depends on anchors Garrett Whitlock and Payton Tolle.

Come playoff time, teams need innings—star power alone isn’t enough.

Key Roles to Watch

These pitchers don’t have to dominate every night, but they’ve got to be steady when it matters most.

Offense, X-Factors, and Tough Decisions Ahead

The lineup runs through Trevor Story, Willson Contreras, and rising stars Wilyer Abreu and Ceddanne Rafaela. Defense and clutch hitting will set the ceiling for Boston’s offense.

Meanwhile, high-upside guys like Marcelo Mayer and Brayan Bello are facing pivotal seasons. Their health and consistency? Still big question marks.

Lingering Questions

Honorable mentions include player-development director Brian Abraham and hitting coach Pete Fatse. These two work behind the scenes and play a big role in Boston’s push to contend.

 
Here is the source article for this story: Who are the most important people in the Red Sox organization? Here’s our Top 20 list.