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

Feb 18, 2019; Lee County, FL, USA; A general view of a Boston Red Sox helmet as Boston Red Sox center fielder Jackie Bradley Jr. (19) walks on the field during a spring training workout at Jet Blue Park at Fenway South. Mandatory Credit: Jasen Vinlove-Imagn Images
Boston Red Sox News

Pair Of Red Sox Top Prospects Added To 40-Man Roster To Avoid Rule 5 Draft Selection

The Boston Red Sox kept two prospects protected as the Rule 5 Draft approaches.

Jackson Roberts
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Aug 15, 2024; San Francisco, California, USA; Atlanta Braves pitcher starting Max Fried (54) delivers against the San Francisco Giants during the first inning at Oracle Park. Mandatory Credit: D. Ross Cameron-Imagn Images
Boston Red Sox News

Red Sox Predicted To Sign $174 Million Two-Time All-Star To Blockbuster Deal

Will the Boston Red Sox land their next number-one starter in free agency this winter?

Jackson Roberts
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Jul 13, 2024; Arlington, TX, USA; American League Future infielder Marcelo Mayer (10) reacts while running to second base with a double during the game against the American League Future team during the Major league All-Star Futures game at Globe Life Field. Mandatory Credit: Kevin Jairaj-Imagn Images
Boston Red Sox News

Red Sox Game-Changing Trade Proposal Lands $13 Million Ace For Superstar Prospect

The Boston Red Sox could land their next number-one starter in a blockbuster trade this winter.

Jackson Roberts
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Oct 29, 2024; New York, New York, USA; New York Yankees outfielder Juan Soto (22) on third base during the first inning in game four of the 2024 MLB World Series against the Los Angeles Dodgers at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images
Boston Red Sox News

What Did Juan Soto Ask Red Sox During Three-Hour Meeting? Insider Shares Details

The Boston Red Sox and free agent Juan Soto recently had a productive meeting, but what did the young superstar ask?

Jackson Roberts
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Sep 19, 2024; Houston, Texas, USA; Houston Astros starting pitcher Yusei Kikuchi (16) pitches as Los Angeles Angels first baseman Nolan Schanuel (18) leads off second base in the first inning at Minute Maid Park. Mandatory Credit: Thomas Shea-Imagn Images
Boston Red Sox News

Red Sox Surprisingly Urged To 'Pass' On All-Star Pitcher With 206 Strikeouts

The Boston Red Sox need pitching, but were recently urged not to pursue one former All-Star.

Jackson Roberts
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Nov 7, 2023; Scottsdale, AZ, USA; Boston Red Six chief baseball officer Craig Breslow speaks to the media during the MLB General Manager's Meetings at Omni Scottsdale Resort & Spa. Mandatory Credit: Mark J. Rebilas-Imagn Images
Boston Red Sox News

Red Sox Strongly Urged To Stay Away From $110 Million Superstar By Insider

One free-agent pitcher was named a bad fit for the Boston Red Sox by an insider.

Jackson Roberts
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Apr 3, 2019; Atlanta, GA, USA; Detailed view of Chicago Cubs hats and gloves in the dugout against the Atlanta Braves in the fifth inning at SunTrust Park. Mandatory Credit: Brett Davis-Imagn Images
Boston Red Sox News

Red Sox Surprise Blockbuster Proposal Lands Cubs $68 Million 'Workhorse'

The Boston Red Sox need starting pitching, and the Chicago Cubs may be willing to send them some.

Jackson Roberts
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Sep 9, 2024; Boston, Massachusetts, USA; Boston Red Sox right fielder Rob Refsnyder (30) is congratulated by eft fielder Jarren Duran (16) after hitting a two run home run against the Baltimore Orioles in the third inning at Fenway Park. Mandatory Credit: David Butler II-Imagn Images
Boston Red Sox News

Red Sox $2 Million Fan-Favorite Surprisingly Named As 'Most Likely' Trade Candidate

One Boston Red Sox outfielder was shockingly named as a possible offseason trade candidate.

Jackson Roberts
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Aug 20, 2024; Houston, Texas, USA; Boston Red Sox starting pitcher Nick Pivetta (37) reacts after a play during the fourth inning against the Houston Astros at Minute Maid Park. Mandatory Credit: Troy Taormina-Imagn Images
Boston Red Sox News

Red Sox Urged To Sign $42 Million All-Star As 'Upgrade' Over Nick Pivetta

The Boston Red sox need starting pitching, especially if Nick Pivetta leaves in free agency.

Jackson Roberts
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Feb 17, 2024; Jupiter, FL, USA; Miami Marlins starting pitcher Sandy Alcantara (22) practices during a spring training workout at the Marlins Player Development & Scouting Complex. Mandatory Credit: Sam Navarro-Imagn Images
Boston Red Sox News

Red Sox Proposed Blockbuster Lands $56M Cy Young Winner Returning From Injury

If the Red Sox are feeling bold this winter, they could take a stab at a superstar pitcher on the trade market.

Jackson Roberts
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Sep 28, 2024; Boston, Massachusetts, USA; Boston Red Sox center fielder Jarren Duran (16) runs off of the field after scoring a run against the Tampa Bay Rays during the sixth inning at Fenway Park. Mandatory Credit: Brian Fluharty-Imagn Images
Boston Red Sox News

Red Sox Superstar Jarren Duran Gives Take On Juan Soto's Fit In Boston

Jarren Duran had a breakout year for the Boston Red Sox, and he recently gave his opinion on whether Juan Soto would fit as his teammate.

Jackson Roberts
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Apr 12, 2024; Philadelphia, Pennsylvania, USA; A view of the field featuring the Philadelphia Phillies City Connect logo before the game against the Pittsburgh Pirates at Citizens Bank Park. Mandatory Credit: Kyle Ross-Imagn Images
Boston Red Sox News

Why Phillies $36 Million All-Star Makes Sense For Red Sox, According To Insider

A Philadelphia Phillies All-Star reliever would fit right in with the Boston Red Sox in 2025.

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