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

Dec 9, 2024; Dallas, TX, USA; Boston Red Sox chief baseball officer Craig Breslow speaks with the media
at the Hilton Anatole during the 2024 MLB Winter Meetings. Mandatory Credit: Jerome Miron-Imagn Images

Boston Red Sox News

Sep 17, 2025; Phoenix, Arizona, USA; Arizona Diamondbacks second base Ketel Marte (4) reacts against the San Francisco Giants in the first inning at Chase Field. Mandatory Credit: Rick Scuteri-Imagn Images

Boston Red Sox News

Aug 26, 2025; St. Louis, Missouri, USA; St. Louis Cardinals first baseman Willson Contreras (40) drives in a run as he grounds out against the Pittsburgh Pirates during the sixth inning at Busch Stadium. Mandatory Credit: Jeff Curry-Imagn Images

Boston Red Sox News

May 7, 2025; Boston, Massachusetts, USA; Boston Red Sox third baseman Alex Bregman (2) runs the bases after hitting a solo home run against the Texas Rangers during the fourth inning at Fenway Park. Mandatory Credit: Brian Fluharty-Imagn Images

Boston Red Sox News

May 25, 2025; Boston, Massachusetts, USA; Boston Red Sox left fielder Jarren Duran (16) bats against the Baltimore Orioles during the first inning at Fenway Park. Mandatory Credit: Brian Fluharty-Imagn Images

Boston Red Sox News

Could the New York Mets now be a trade fit for a dynamic Boston Red Sox outfielder?

Mar 4, 2025; Bradenton, Florida, USA; Boston Red Sox second base Vaughn Grissom (5) singles during the fourth inning against the Pittsburgh Pirates at LECOM Park. Mandatory Credit: Kim Klement Neitzel-Imagn Images

Boston Red Sox News

The former Boston Red Sox infielder is excited to become a member of the Los Angeles Angels.

Aug 5, 2025; Seattle, Washington, USA; A fan holds up a sign after as Seattle Mariners third baseman Eugenio Suarez (28) runs the bases after hitting a 2-run home run against the Chicago White Sox during the fourth inning at T-Mobile Park. Mandatory Credit: Steven Bisig-Imagn Images

Boston Red Sox News

The pathway to the Boston Red Sox acquiring Eugenio Suárez seems to be clearing up, whether fans like it or not.

Sep 19, 2025; Phoenix, Arizona, USA; Arizona Diamondbacks infielder Ketel Marte (4) after hitting a home run in the first inning against the Philadelphia Phillies at Chase Field. Mandatory Credit: Allan Henry-Imagn Images

Boston Red Sox News

According to an insider, the Arizona Diamondbacks now believe this All-Star will be traded. That could be huge for the Boston Red Sox.

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

The Boston Red Sox seem to know they can't afford to lose out on Alex Bregman in free agency at this juncture.

Sep 10, 2025; Arlington, Texas, USA; Milwaukee Brewers starting pitcher Freddy Peralta (51) and catcher Danny Jansen (33) walk to the dugout before the first inning against the Texas Rangers at Globe Life Field. Mandatory Credit: Jim Cowsert-Imagn Images

Boston Red Sox News

The Boston Red Sox don't have the momentum in the division race at all. It's time to change that.

Sep 6, 2019; St. Petersburg, FL, USA; A detail view of a Tampa Bay Rays hat and glove at Tropicana Field. Mandatory Credit: Kim Klement-Imagn Images

Boston Red Sox News

The Tampa Bay Rays scooped up four-year Boston Red Sox minor leaguer Alvaro Mejias in the Rule 5 Draft.

Jul 22, 2025; Arlington, Texas, USA; Athletics glove and hat on the field before the game against the Texas Rangers at Globe Life Field. Mandatory Credit: Kevin Jairaj-Imagn Images

Boston Red Sox News

The Boston Red Sox have a new right-handed pitcher, a full 40-man roster, and a lot of work still to do in free agency.

Salem's Jedixson Paez (17) pitches against the Shorebirds Tuesday, April 9, 2024, at Perdue Stadium in Salisbury, Maryland.

Boston Red Sox News

The Chicago White Sox made a move the Boston Red Sox almost definitely did not see coming on Wednesday.

Apr 29, 2025; Toronto, Ontario, CAN; Toronto Blue Jays shortstop Bo Bichette (11) gets caught trying to steal third base against Boston Red Sox third baseman Alex Bregman (2) during the first inning at Rogers Centre. Mandatory Credit: John E. Sokolowski-Imagn Images

Boston Red Sox News

The Toronto Blue Jays are spending money freely this offseason, and the Boston Red Sox may have to be leery of that.

Sep 17, 2018; Atlanta, GA, USA; Detailed view of a St. Louis Cardinals hat and glove in the dugout against the Atlanta Braves in the first inning at SunTrust Park. Mandatory Credit: Brett Davis-Imagn Images

Boston Red Sox News

Are the Boston Red Sox considering a second blockbuster trade with the St. Louis Cardinals?

Pitcher Bryan Mata throws two simulated innings before the WooSox game on Sept. 14, 2023.

Boston Red Sox News

Once among the top prospects in the Boston Red Sox organization, Bryan Mata is headed overseas without having made his major league debut.