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@moreviewsmedia.com

Oct 23, 2026; Milwaukee, Wisconsin, USA; General view of the pregame ceremony before game one of the 2026 World Series between Tampa Bay Rays and Milwaukee Brewers at American Family Field. Mandatory Credit: Matt Marton-Imagn Images

Boston Red Sox News

Aug 15, 2026; Pittsburgh, Pennsylvania, USA; Boston Red Sox starting pitcher Sonny Gray (54) delivers a pitch against the Pittsburgh Pirates during the first inning at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images

Boston Red Sox News

Apr 6, 2026; Boston, Massachusetts, USA; Milwaukee Brewers shortstop David Hamilton (6) tags out Boston Red Sox third baseman Caleb Durbin (5) during the second inning at Fenway Park. Mandatory Credit: Paul Rutherford-Imagn Images

Boston Red Sox News

Oct 20, 2022; Houston, Texas, USA; New York Yankees hitting coach Dillon Lawson takes notes before game two of the ALCS against the New York Yankees for the 2022 MLB Playoffs at Minute Maid Park. Mandatory Credit: Thomas Shea-USA TODAY Sports

Boston Red Sox News

Sep 30, 2026; San Diego, California, USA; Chicago Cubs outfielder Seiya Suzuki (27) strikes out in the fifth inning against the San Diego Padres during game two of the Wildcard round for the 2026 MLB Playoffs at Petco Park. Mandatory Credit: Denis Poroy-Imagn Images

Boston Red Sox News

How can the Boston Red Sox have a productive winter? Here are our best ideas.

Sep 29, 2026; Bronx, New York, USA; Boston Red Sox first baseman Willson Contreras (40) is introduced before game one of the Wildcard round for the 2026 MLB Playoffs against the New York Yankees at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images

Boston Red Sox News

The Boston Red Sox aren't as good as the teams still competing for a World Series. Here's why.

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

As the Boston Red Sox enter a tricky offseason with respect to the 40-man roster, a number of names are under the microscope. A couple of years ago, it would h

Sep 19, 2026; St. Petersburg, Florida, USA; Boston Red Sox pitcher Garrett Whitlock (22) walks to the clubhouse after he gave up the game winning RBI hit to Tampa Bay Rays second baseman Richie Palacios (1) after he during the ninth inning at Tropicana Field. Mandatory Credit: Kim Klement Neitzel-Imagn Images

Boston Red Sox News

Everything the Boston Red Sox do is under a microscope, and after they botched their injury communication for most of the season, nothing they do at this point

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

Let's dissect the Boston Red Sox's early offseason budget questions.

Sep 30, 2026; Bronx, New York, USA; Boston Red Sox pitcher Sonny Gray (54) looks on after New York Yankees first baseman Luis Garcia Jr. (26) hits a home run in the fourth inning during game two of the Wildcard round for the 2026 MLB Playoffs at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images

Boston Red Sox News

The Boston Red Sox's season eulogies have all been read, but the one thing that some still considered to be up for debate was Sonny Gray. In Game 2 of last wee

Sep 19, 2026; Denver, Colorado, USA; Colorado Rockies catcher Hunter Goodman (15) at third base in the seventh inning against the Seattle Mariners at Coors Field. Mandatory Credit: Christopher Hanewinckel-Imagn Images

Boston Red Sox News

A list of trade candidates who make sense as fits for the Boston Red Sox.

Sep 30, 2026; Bronx, New York, USA; Boston Red Sox pitcher Garrett Crochet (35) is relieved in the sixth inning against the New York Yankees during game two of the Wildcard round for the 2026 MLB Playoffs at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images

Boston Red Sox News

The Boston Red Sox have come up embarrassingly short in the playoffs over and over again.

Aug 26, 2026; Miami, Florida, USA; Boston Red Sox pitcher Sonny Gray (54) delivers a pitch against the Miami Marlins during the first inning at loanDepot Park. Mandatory Credit: Sam Navarro-Imagn Images

Boston Red Sox News

The Boston Red Sox need to follow a fairly concrete plan this winter, and it looks like this.

Sep 23, 2026; Boston, Massachusetts, USA; Boston Red Sox pitcher Aroldis Chapman (44) reacts to getting the final out against the Cleveland Guardians during the ninth inning at Fenway Park. Mandatory Credit: Gregory Fisher-Imagn Images

Boston Red Sox News

The Boston Red Sox's fireballing closer passed the physical that locked him into his 2027 contract.

Aug 21, 2026; Boston, Massachusetts, USA; Boston Red Sox left fielder Jarren Duran (16) catches a fly ball during the fourth inning against the San Francisco Giants at Fenway Park. Mandatory Credit: Paul Rutherford-Imagn Images

Boston Red Sox News

The Boston Red Sox have a very simple trade they're finally likely to pull the trigger on this offseason.

Sep 24, 2026; Chicago, Illinois, USA; Chicago Cubs right fielder Seiya Suzuki (27) hits a home run during the fifth inning against the Miami Marlins at Wrigley Field. Mandatory Credit: Matt Marton-Imagn Images

Boston Red Sox News

The Boston Red Sox had real flaws. Let's fix some of them in hypothetical free agency.