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

Mar 18, 2025; Tampa, Florida, USA; Boston Red Sox outfielder Masataka Yoshida (7) runs the bases after hitting a two run home run against the New York Yankees in the sixth inning during spring training at George M. Steinbrenner Field. Mandatory Credit: Nathan Ray Seebeck-Imagn Images
Boston Red Sox News

Red Sox Predicted To Unceremoniously Dump $90 Million Slugger In Midseason Trade

When could the Boston Red Sox cut ties with this slugger, who doesn't seem to have a position?

Jackson Roberts
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Feb 28, 2025; Clearwater, Florida, USA; Boston Red Sox starting pitcher Garrett Crochet (35) throws a pitch during the first inning against the Philadelphia Phillies at BayCare Ballpark. Mandatory Credit: Kim Klement Neitzel-Imagn Images
Boston Red Sox News

Red Sox's Craig Breslow Gives Bleak Garrett Crochet Extension Update On Opening Day

The Boston Red Sox aren't going to get an extension in under the wire for ace pitcher Garrett Crochet.

Jackson Roberts
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Sep 20, 2019; St. Petersburg, FL, USA; A detail view of Boston Red Sox hats and gloves at Tropicana Field. Mandatory Credit: Kim Klement-Imagn Images
Boston Red Sox News

Red Sox 3-Time All-Star Suffers Brutal Injury Setback Just Before Season Opener

One Boston Red Sox reliever unexpectedly hit the injured list on Opening Day.

Jackson Roberts
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Mar 11, 2025; Peoria, Arizona, USA; San Diego Padres pitcher Dylan Cease greets teammates against the Chicago White Sox during a spring training game at Peoria Sports Complex. Mandatory Credit: Mark J. Rebilas-Imagn Images
Boston Red Sox News

Red Sox Predicted To Land Padres $109M Cy Young Contender In Massive 6-Player Swap

The Boston Red Sox were recently predicted to acquire a superstar pitcher at the 2025 MLB trade deadline.

Jackson Roberts
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Sep 22, 2024; Boston, Massachusetts, USA; Wally the Boston Red Sox mascot celebrates the team's win over the Minnesota Twins at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images
Boston Red Sox News

Bold Predictions For Red Sox's 2025 Season: MVP, Biggest Disappointment, And More

Who will stand out for the 2025 Boston Red Sox?

Jackson Roberts
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Aug 25, 2024; Boston, Massachusetts, USA; Boston Red Sox third baseman Rafael Devers (11) runs the bases after hitting a three run home run against the Arizona Diamondbacks during the fourth inning at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images
Boston Red Sox News

Red Sox All-Star Rafael Devers Gives Honest Reaction To Forced Position Change

How did Boston Red Sox designated hitter Rafael Devers feel about being moved off third base?

Jackson Roberts
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May 12, 2024; Boston, Massachusetts, USA; A bag of baseballs sits on the diamond before a game against between the Boston Red Sox and the Washington Nationals at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images
Boston Red Sox News

Red Sox Predicted To Trade For $56 Million Superstar To Pair With Garrett Crochet

The Boston Red Sox could pull off a massive trade to land a second ace pitcher at some point this season.

Jackson Roberts
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Feb 15, 2025; Lee County, FL, USA; Boston Red Sox shortstop Marcelo Mayer (38) throws the ball to second base during spring training at Jet Blue Park at Fenway South Credit Chris Tilley-Imagn Images
Boston Red Sox News

Red Sox's Marcelo Mayer Makes Bold Declaration Ahead Of 2026 World Baseball Classic

Will we see Marcelo Mayer play in the 2026 World Baseball Classic?

Jackson Roberts
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Boston's top-three prospects in Marcelo Mayer, Kristian Campbell and Roman Anthony stand for the national anthem ahead of a Spring Training breakout game on March 13, 2025.
Boston Red Sox Prospects

This Red Sox 'Big 3' Star Will Win Rookie Of The Year, Says Top Prospect Evaluator

The Boston Red Sox could boast a Rookie of the Year winner for the first time since 2007.

Jackson Roberts
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Mar 17, 2025; Fort Myers, Florida, USA; Boston Red Sox first baseman Triston Casas (36) throws the ball to first for the out during the third inning of their game against the Baltimore Orioles at JetBlue Park at Fenway South. Mandatory Credit: Chris Tilley-Imagn Images
Boston Red Sox News

Red Sox Predicted To Reverse Course On Triston Casas Trade By End Of 2025

What does the future hold for Triston Casas in Boston?

Jackson Roberts
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Sep 12, 2024; Bronx, New York, USA; Boston Red Sox first baseman Connor Wong (12) runs out a double against the New York Yankees during the second inning at Yankee Stadium. Mandatory Credit: Gregory Fisher-Imagn Images
Boston Red Sox News

Red Sox Predicted To Replace Connor Wong; Phillies $115M Star Floated As Trade Fit

Could Boston Red Sox catcher Connor Wong be replaced by the Philadelphia Phillies' three-time All-Star.

Jackson Roberts
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Sep 27, 2024; Anaheim, California, USA; Texas Rangers pitcher Jacob deGrom (48) throws against the Los Angeles Angels during the first inning at Angel Stadium. Mandatory Credit: Gary A. Vasquez-Imagn Images
Boston Red Sox News

Do The Red Sox Face Jacob deGrom? Rangers Set Rotation For 2025 Opening Weekend

The Boston Red Sox found out which pitchers they'll be facing in their first series of the new season.

Jackson Roberts
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