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

Aug 21, 2025; Tampa, Florida, USA; St. Louis Cardinals first baseman Willson Contreras (40) runs the bases after hitting a home run against the Tampa Bay Rays in the seventh inning at George M. Steinbrenner Field. Mandatory Credit: Nathan Ray Seebeck-Imagn Images

Boston Red Sox News

May 13, 2022; Phoenix, Arizona, USA; Chicago Cubs catcher Willson Contreras (40) reacts after getting tagged out by Arizona Diamondbacks second baseman Ketel Marte (4) trying to steal second base in the first inning at Chase Field. Mandatory Credit: Rick Scuteri-Imagn Images

Boston Red Sox News

Sep 15, 2025; St. Louis, Missouri, USA; St. Louis Cardinals first baseman Willson Contreras (40) celebrates after hitting a RBI single against the Cincinnati Reds in the sixth inning at Busch Stadium. Mandatory Credit: Joe Puetz-Imagn Images

Boston Red Sox News

Aug 27, 2025; Baltimore, Maryland, USA; Boston Red Sox outfielder Roman Anthony (19) rounds the bases on a solo home run during the first inning against the Baltimore Orioles at Oriole Park at Camden Yards. Mandatory Credit: James A. Pittman-Imagn Images

Boston Red Sox News

May 18, 2025; Boston, Massachusetts, USA; A Boston Red Sox hat and glove rests on the railing by the dugout prior to a game against the Atlanta Braves at Fenway Park. Mandatory Credit: Bob DeChiara-Imagn Images

Boston Red Sox News

A common sentiment is spreading that this top prospect could debut for the Boston Red Sox this year.

Aug 12, 2025; Houston, Texas, USA; Boston Red Sox third baseman Alex Bregman (2) hits a home run during the sixth inning against the Houston Astros at Daikin Park. Mandatory Credit: Troy Taormina-Imagn Images

Boston Red Sox News

The Boston Red Sox have to get serious about bringing Alex Bregman back. Enough is enough.

Apr 14, 2025; St. Louis, Missouri, USA; St. Louis Cardinals first baseman Willson Contreras (40) celebrates with shortstop Brendan Donovan (33) after scoring against the Houston Astros during the fifth inning at Busch Stadium. Mandatory Credit: Jeff Curry-Imagn Images

Boston Red Sox News

The Boston Red Sox and St. Louis Cardinals make sense as a fit for one more trade this winter.

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

The Boston Red Sox cannot continue living as the only American League team without a free-agent signing.

Apr 29, 2025; Toronto, Ontario, CAN; Boston Red Sox third baseman Alex Bregman (2) rounds second base after hitting a solo home run against the Toronto Blue Jays during the first inning at Rogers Centre. Mandatory Credit: John E. Sokolowski-Imagn Images

Boston Red Sox News

The Boston Red Sox surely don't need the Toronto Blue Jays driving up the bidding war for Alex Bregman.

WooSox player Jhostynxon Garcia comes off the field at Polar Park during a game on May 25, 2025. The player nicknamed 'The Password' is starting to get pregame work in playing first base with Triple-A Worcester.

Boston Red Sox News

The Boston Red Sox cut ties with Jhostynxon Garcia in a trade this month, and the outfielder had an emotional parting message for the fan base.

Aug 31, 2025; Los Angeles, California, USA; Arizona Diamondbacks second baseman Ketel Marte (4) is greeted in the dugout after scoring a run during the fourth inning against the Los Angeles Dodgers at Dodger Stadium. Mandatory Credit: Jayne Kamin-Oncea-Imagn Images

Boston Red Sox News

If the Boston Red Sox want to trade for Ketel Marte, they'd better be prepared for it to hurt.

Apr 3, 2025; Baltimore, Maryland, USA; Boston Red Sox third baseman Alex Bregman (2) prior to the game against the Baltimore Orioles at Oriole Park at Camden Yards. Mandatory Credit: Mitch Stringer-Imagn Images

Boston Red Sox News

Alex Bregman will play for the Boston Red Sox next season: true or false?

Sep 28, 2024; Boston, Massachusetts, USA; Boston Red Sox starting pitcher Kutter Crawford (50) walks of the field after being taken out of the game in the fifth inning against the Tampa Bay Rays at Fenway Park. Mandatory Credit: Brian Fluharty-Imagn Images

Boston Red Sox News

The Boston Red Sox have two arms making progress, but neither is quite ready to slot into a rotation.

Jun 29, 2024; Boston, Massachusetts, USA; San Diego Padres starting pitcher Michael King (34) pitches during the first inning against the Boston Red Sox at Fenway Park. Mandatory Credit: Bob DeChiara-Imagn Images

Boston Red Sox News

The Boston Red Sox never made a ton of sense for Michael King, and now that he's off the table, it's back to focusing on what matters.

Aug 26, 2025; Baltimore, Maryland, USA; Boston Red Sox shortstop Trevor Story (10) throws to first base during the ninth inning against the Baltimore Orioles at Oriole Park at Camden Yards. Mandatory Credit: James A. Pittman-Imagn Images

Boston Red Sox News

Are the Boston Red Sox counting too heavily on their veteran shortstop this season?

Feb 18, 2025; Lee County, FL, USA; Boston Red Sox pitcher Luis Perales (93) participates in media day at JetBlue Park at Fenway South. Mandatory Credit: Nathan Ray Seebeck-Imagn Images

Boston Red Sox News

Former Boston Red Sox prospect Luis Perales recently spoke about being traded to the Washington Nationals.