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 10, 2025; Kansas City, Missouri, USA; A general view of a Boston Red Sox's cap and glove on the field before a game against the Kansas City Royals at Kauffman Stadium. Mandatory Credit: Peter Aiken-Imagn Images

Boston Red Sox News

Apr 6, 2025; Boston, Massachusetts, USA; Boston Red Sox catcher Carlos Narvaez (75) and relief pitcher Cooper Criswell (64) celebrate defeating the St. Louis Cardinals at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images

Boston Red Sox News

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

Oct 8, 2025; Los Angeles, California, USA; Philadelphia Phillies designated hitter Kyle Schwarber (12) looks into the dugout after hitting a solo home run during the fourth inning against the Los Angeles Dodgers in game three of the NLDS during the 2025 MLB playoffs at Dodger Stadium. Mandatory Credit: Jayne Kamin-Oncea-Imagn Images

Boston Red Sox News

Jul 22, 2019; St. Petersburg, FL, USA; A detail view of Boston Red Sox hat and glove laying in the dugout at Tropicana Field. Mandatory Credit: Kim Klement-Imagn Images

Boston Red Sox News

Someone is getting dropped from the Boston Red Sox's 40-man roster on Thursday, but who?

Apr 22, 2025; Boston, Massachusetts, USA; Boston Red Sox first base Triston Casas (36) hits a three run home run against the Seattle Mariners in the seventh inning at Fenway Park. Mandatory Credit: David Butler II-Imagn Images

Boston Red Sox News

Could the Boston Red Sox be going after Pete Alonso in free agency? That's what an insider believes Triston Casas could be telling us.

Sep 10, 2025; Cumberland, Georgia, USA; Atlanta Braves starting pitcher Chris Sale (51) pitches against the Chicago Cubs during the first inning at Truist Park. Mandatory Credit: Dale Zanine-Imagn Images

Boston Red Sox News

How on earth did the Atlanta Braves luck out this much with Chris Sale's contract?

Aug 27, 2025; Baltimore, Maryland, USA; Boston Red Sox third baseman Alex Bregman (2) gestures on the field before the game between the Baltimore Orioles and the Boston Red Sox at Oriole Park at Camden Yards. Mandatory Credit: James A. Pittman-Imagn Images

Boston Red Sox News

Boston Red Sox fans worried about Alex Bregman's departure just got some new anxiety-inducing reading material.

Sep 28, 2024; Boston, Massachusetts, USA; Boston Red Sox first baseman Triston Casas (36) walks off of the field after striking out against the Tampa Bay Rays during the eighth inning at Fenway Park. Mandatory Credit: Brian Fluharty-Imagn Images

Boston Red Sox News

Boston Red Sox first baseman Triston Casas had an odd message to share on his Instagram page on Tuesday.

Mar 5, 2019; West Palm Beach, FL, USA; A detailed view of a Boston Red Sox cap, sunglasses and glove in the dugout during a spring training game between the Washington Nationals and the Boston Red Sox at FITTEAM Ballpark of the Palm Beaches. Mandatory Credit: Jasen Vinlove-Imagn Images

Boston Red Sox News

The Boston Red Sox made the fairly obvious decision not to reunite with this once-great relief pitcher.

Sep 7, 2025; Phoenix, Arizona, USA; Boston Red Sox shortstop Trevor Story against the Arizona Diamondbacks at Chase Field. Mandatory Credit: Mark J. Rebilas-Imagn Images

Boston Red Sox News

The Boston Red Sox have Trevor Story back under contract for the next two years, possibly even three. Now what?

Sep 9, 2025; West Sacramento, California, USA; Boston Red Sox left fielder Jarren Duran (16) warms up before the game against the Athletics at Sutter Health Park. Mandatory Credit: Sergio Estrada-Imagn Images

Boston Red Sox News

The Boston Red Sox and Jarren Duran are in agreement on a new one-year deal for next season.

Aug 12, 2023; Toronto, Ontario, CAN; A Chicago Cubs helmet rests on the dugout during a MLB game against the Toronto Blue Jays at Rogers Centre. Mandatory Credit: Kevin Sousa-Imagn Images

Boston Red Sox News

This Boston Red Sox impending free agent still has a lot of outcomes on the table. Is signing with the Chicago Cubs one of them?

Aug 8, 2025; San Diego, California, USA; Boston Red Sox right fielder Wilyer Abreu (52) hits a two-run home run during the fourth inning against the San Diego Padres at Petco Park. Mandatory Credit: Denis Poroy-Imagn Images

Boston Red Sox News

The Boston Red Sox have a two-time Gold Glove right fielder who might now be on the trade market.

Sep 30, 2025; Bronx, New York, USA; Boston Red Sox pitcher Garrett Crochet (35) throws a pitch during the fourth inning against the New York Yankees during game one of the Wildcard round for the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images

Boston Red Sox News

The Boston Red Sox's trade for Garrett Crochet and subsequent extension have worked like a charm.

Aug 29, 2014; St. Petersburg, FL, USA; A detailed view of Boston Red Sox left fielder Yoenis Cespedes (52) helmet in the dugout against the Tampa Bay Rays at Tropicana Field. Mandatory Credit: Kim Klement-Imagn Images

Boston Red Sox News

The Boston Red Sox might struggle to meet the price tag for their star player if this projection proves accurate.