Exclusive: An Interview with NESN Reporter Jahmai Webster
- Eric Stoller
- 12 minutes ago
- 2 min read
BOSTON- When attending a Red Sox game at Fenway Park, you never know what to expect. Nor had Dean Daily’s reporter, Eric Stoller, before walking through the Fenway Park gates 1.5 hours prior to first pitch on a mild temp April 7th night—when the Boston Red Sox hosted the Milwaukee Brewers at 6:45 pm.
This past Tuesday, The Dean Daily attended their first Red Sox game of the 2026 season. Upon entering the ballpark, the Dean Daily proceeded directly to the Red Sox dugout where NESN sideline reporter, Jahmai Webster, was on field, reporting live for the Red Sox pregame.
Once off-air, Jahmai sat himself right in the Red Sox dugout where he toggled back-and-forth between his mobile phone and mini notebook which he was continuously jotted down information into.
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He had been prepping for a lengthy period. While the passionate, young fans surrounding us were emphatically vying for player autographs and souvenir balls, the intent was to observe and discover more about Jahmai’s role and his 10 years of experience covering the Boston Red Sox.
Without any hesitation, The Dean Daily asked if he would be willing to conduct a short interview and answer brief questions that had been developed. Webster stood up right up from the bench, walked over kindly offering three minutes of his valuable time.
To begin the interview, the first question to Webster asked him to reflect on his 10 years spent covering the Red Sox since 2016, involving what excites him the most, and the growth he has seen throughout that span.
Webster answered, “I enjoy the spontaneity of all which is great and that’s what really keeps me coming back.” In terms of growth, he has greatly relied on his curiosity of the game and the stated ability to “lean on experts”, such as the players, clubhouse, writers and broadcasting personnel. Webster praised his team around him, allowing him to improve and expand his curiosity and baseball insight. He also mentioned how each day is different for him.
Aside from each day being unique, so is every new season he covers. Despite the change, The Dean Daily next asked Webster whether he annually alters his new season approach, regardless of the seasonal outcome. Webster confirmed that his approach essentially remains the same.
More specifically, Webster emphasized the importance on staying factually correct but also gaining trust from the players and fans. He noted that “the foundation is always the same, but the faces change."
Finally, he was asked about his coverage flexibility regarding initiating covered stories versus assigned reporting. Webster re-emphasized the critical component of curiousness. He noted that most of his coverage comes from his curiosity and ideas developed from watching the team. Though, he did mention that it is also a “collaborative effort” with some ideas chosen by the producers.
Overall, The Dean Daily greatly enjoyed getting to know Jahmai Webster and having the chance to learn more about his analyst role.
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