Inside The Red Sox
Jackson Roberts

Jackson Roberts

Joined: Aug 12, 2024

Jackson Roberts is a former Division III All-Region DH who now writes and talks about sports for a living. A Bay Area native and a graduate of Swarthmore College and the Newhouse School at Syracuse University, Jackson makes his home in North Jersey. He grew up rooting for the Red Sox, Patriots, and Warriors, and he recently added the Devils to his sports fandom mosaic. For all business/marketing inquiries regarding Boston Red Sox On SI, please reach out to Scott Neville: scott@wtfsports.org

May 13, 2023; Boston, Massachusetts, USA; Boston Red Sox chief baseball officer Chaim Bloom signs an autograph prior to a game against the against the St. Louis Cardinals at Fenway Park. Mandatory Credit: Bob DeChiara-Imagn Images
Boston Red Sox News

Ex-Red Sox GM Could Become Cardinals' Top Decision-Maker, Per Insider

The Boston Red Sox fired their top baseball executive just over a year ago to date, and now that exec appears poised for another shot at a decision-making gig.

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Sep 15, 2024; Bronx, New York, USA; Boston Red Sox starting pitcher Kutter Crawford (50) pitches in the first inning against the New York Yankees at Yankee Stadium. Mandatory Credit: Wendell Cruz-Imagn Images
Boston Red Sox News

Red Sox Show Their True Colors In Back-Breaking Loss To Yankees

The Boston Red Sox dropped to .500 after a 5-2 loss against the rival New York Yankees on Sunday.

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Aug 16, 2024; Baltimore, Maryland, USA; Boston Red Sox manager Alex Cora (13) stands in the dugout during the first inning of the game against the Baltimore Orioles at Oriole Park at Camden Yards. Mandatory Credit: Tommy Gilligan-Imagn Images
Boston Red Sox News

Why Red Sox Could Soon Be Thanking Yankees' Gerrit Cole, Per Alex Cora

The Boston Red Sox and New York Yankees renewed their storied rivalry on Saturday, with some verbal jabs thrown by the Boston skipper.

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Sep 14, 2024; Bronx, New York, USA; Boston Red Sox third baseman Rafael Devers (11) high fives right fielder Wilyer Abreu (52) after defeating the New York Yankees at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images
Boston Red Sox News

Red Sox, Rafael Devers Shocked By Gerrit Cole's Free Pass: 'He Panicked A Little Bit'

The Boston Red Sox's star third baseman was issued an unusual free pass on Saturday by the New York Yankees' Gerrit Cole.

Jackson Roberts
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Sep 14, 2024; Bronx, New York, USA; New York Yankees starting pitcher Gerrit Cole (45) reacts during the fifth inning against the Boston Red Sox at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images
Boston Red Sox News

Yankees' Historic Intentional Walk Of Red Sox Star Has Everyone Shaking Their Heads

The New York Yankees' ace intentionally walked the Boston Red Sox's best hitter on Saturday, causing quite a stir.

Jackson Roberts
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Aug 22, 2024; Baltimore, Maryland, USA; Baltimore Orioles pitcher Corbin Burnes (39) greeted by catcher Adley Rutschman (35) at the end of the third inning against the Houston Astros at Oriole Park at Camden Yards. Mandatory Credit: Mitch Stringer-Imagn Images
Boston Red Sox News

Superstar Free Agent Weighs Coming To Red Sox: 'Do These Guys Have Money To Spend?'

Entering a pivotal free agency, one superstar pitcher spoke about the possibility of joining the Boston Red Sox.

Jackson Roberts
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Sep 11, 2024; Boston, Massachusetts, USA; Boston Red Sox left fielder Tyler O'Neill (17) his a three run home run to win the game against the Baltimore Orioles in ten innings at Fenway Park. Mandatory Credit: David Butler II-Imagn Images
Boston Red Sox News

Red Sox's Most Productive Slugger 'Likely' To Reject Boston's Qualifying Offer

The Boston Red Sox have a difficult decision to make involving one of their most productive hitters this season.

Jackson Roberts
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May 12, 2018; Detroit, MI, USA; Hat and glove of Seattle Mariners center fielder Dee Gordon (9) sits in dugout during the third inning against the Detroit Tigers at Comerica Park. Mandatory Credit: Rick Osentoski-Imagn Images
Boston Red Sox News

Red Sox Blockbuster Trade Proposal Lands Mariners Ace For Lefty Slugger

The Boston Red Sox need starting pitching, and perhaps the answer lies in a deal with the ace-laden Seattle Mariners.

Jackson Roberts
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May 24, 2024; Boston, Massachusetts, USA; Milwaukee Brewers shortstop Willy Adames (27) reacts to hitting a double against the Boston Red Sox during the ninth inning at Fenway Park. Mandatory Credit: Gregory Fisher-Imagn Images
Boston Red Sox News

Insider: Red Sox Could Add Projected $150 Million Star To Address Biggest Weakness

The Boston Red Sox have far too much left-handed hitting, and one insider believes that could be solved by adding a superstar free agent.

Jackson Roberts
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Aug 10, 2024; Boston, Massachusetts, USA; Houston Astros third baseman Alex Bregman (2) rounds the bases after hitting a home run during the seventh inning against the Boston Red Sox at Fenway Park. Mandatory Credit: Bob DeChiara-Imagn Images
Boston Red Sox News

Insider Says Red Sox Could Sign Astros Superstar, Trade Young Lefty Slugger

The Boston Red Sox have too many left-handers in their lineup, and one insider's solution might seem radical at first glance

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Jul 5, 2024; Bronx, New York, USA; Boston Red Sox center fielder Ceddanne Rafaela (43) and right fielder Wilyer Abreu (52) celebrates after defeating the New York Yankees at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images
Boston Red Sox News

Red Sox Could Trade Rookie Of The Year Candidate To Make Room For Star Prospect

The Boston Red Sox have a roster crunch coming up, and the front office will have to decide whether to sell high on a young star.

Jackson Roberts
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Jul 11, 2024; Boston, Massachusetts, USA; Boston Red Sox relief pitcher Chase Anderson (48) and catcher Connor Wong (12) reacts after defeating the Oakland Athletics in nine innings at Fenway Park. Mandatory Credit: David Butler II-Imagn Images
Boston Red Sox News

Ex-Red Sox Hurler DFA'd By Reigning World Champs, Clearing Room For Top Prospect

A former Boston Red Sox pitcher finds himself without a team again after the Texas Rangers let him go on Thursday.

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