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

Apr 15, 2023; San Diego, California, USA; San Diego Padres second baseman Ha-Seong Kim wears a hat with the Jackie Robinson commemorative logo during the game against the Milwaukee Brewers at Petco Park. Mandatory Credit: Ray Acevedo-Imagn Images
Boston Red Sox News

Padres $49 Million Gold Glover 'Who Won't Be Back' Is Ideal Red Sox Target

If the Boston Red Sox want to improve their defense, a San Diego Padres star should be at the top of their list.

Jackson Roberts
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Jul 22, 2017; Anaheim, CA, USA; A fan of the Boston Red Sox wears Red Sox logo sunglasses during a MLB baseball game against the Los Angeles Angels at Angel Stadium of Anaheim. Mandatory Credit: Kirby Lee-Imagn Images
Boston Red Sox News

Red Sox Predicted To 'Spend Big' On $65 Million Lefty In Free Agency By Insider

With the Boston Red Sox seeking relief pitching, one insider's prediction sees them going hard after a superstar closer.

Jackson Roberts
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Aug 14, 2023; Atlanta, Georgia, USA; A detailed view of a New York Yankees hat and glove on the bench against the Atlanta Braves in the third inning at Truist Park. Mandatory Credit: Brett Davis-Imagn Images
Boston Red Sox News

Insider Calls Red Sox 'Long Shot' For Four-Time All-Star Projected For $513 Million

The Boston Red Sox don't seem to have a very good chance at landing the hottest free agent on this winter's market.

Jackson Roberts
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Apr 3, 2021; Miami, Florida, USA; A general view of the Miami Marlins logo silhouetted against the sky at loanDepot park prior to the game between the Miami Marlins and the Tampa Bay Rays. Mandatory Credit: Jasen Vinlove-Imagn Images
Boston Red Sox News

Insider Names Recent Cy Young Winner As Red Sox Blockbuster Trade Target

How will the Boston Red Sox look to improve their rotation this winter?

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 Could Acquire Cubs Lefty All-Star In Offseason Blockbuster, Insider Says

Could the Boston Red Sox shock the baseball world with a trade involving a Chicago Cubs ace?

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 Could Trade For Mariners Breakout Star With 2.94 ERA, Per Insider

The Boston Red Sox need starting pitching, and that's something the Seattle Mariners have in spades.

Jackson Roberts
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Sep 5, 2023; Atlanta, Georgia, USA; A detailed view of the hat and glove of St. Louis Cardinals second baseman Nolan Gorman (not pictured) before a game against the Atlanta Braves at Truist Park. Mandatory Credit: Brett Davis-Imagn Images
Boston Red Sox News

Could Red Sox Add Projected $13 Million Former MVP To Bolster Lineup?

The Boston Red Sox could make one of the most shocking moves of the offseason.

Jackson Roberts
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Sep 16, 2024; Atlanta, Georgia, USA; Atlanta Braves starting pitcher Max Fried (54) throws against the Los Angeles Dodgers in the third inning at Truist Park. Mandatory Credit: Brett Davis-Imagn Images
Boston Red Sox News

Red Sox Predicted To Pursue Two-Time All-Star Projected To Get $149 Million

The Boston Red Sox are among the top teams expected to pursue an Atlanta Braves ace.

Jackson Roberts
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Sep 24, 2024; Bronx, New York, USA; Baltimore Orioles right fielder Anthony Santander (25) hits a solo home run during the sixth inning against the New York Yankees at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images
Boston Red Sox News

Red Sox Named As Threat To Sign Away $97 Million Superstar From AL East Rival

The Boston Red Sox have holes to plug this winter, and one of them could lead to pursuing a Baltimore Orioles slugger.

Jackson Roberts
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May 24, 2023; Washington, District of Columbia, USA; San Diego Padres hats in the dugout during the game against the Washington Nationals at Nationals Park. Mandatory Credit: Brad Mills-Imagn Images
Boston Red Sox News

Insider Floats Padres First-Time All-Star As Possible Impact Signing For Red Sox

The Boston Red Sox could be an option for a San Diego Padres All-Star set to hit free agency.

Jackson Roberts
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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

Red Sox Urged To Reunite With 2013 World Series Champion Let Go By Cubs

The Boston Red Sox have a new opening at first-base coach, and a former World Series champion could make sense as a replacement hire.

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 Linked To '$300-plus Million' Ace As Possible Blockbuster Free Agent Signing

The Boston Red Sox may have to pay over $300 million if they want to land this top-tier free agent pitcher.

Jackson Roberts
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