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 28, 2025; Arlington, Texas, USA; A Texas Rangers cap and baseball mitt sit on the dugout steps during a game against the Athletics at Globe Life Field. Mandatory Credit: Raymond Carlin III-Imagn Images

Boston Red Sox News

Oct 31, 2023; Phoenix, Arizona, USA; Fox Sports reporter Ken Rosenthal during the Arizona Diamondbacks game against the Texas Rangers in game four of the 2023 World Series at Chase Field. Mandatory Credit: Mark J. Rebilas-USA TODAY Sports

Boston Red Sox News

Aug 26, 2025; Baltimore, Maryland, USA; Boston Red Sox pitcher Justin Wilson (right) and catcher Carlos Narvaez (left) celebrate the win against the Baltimore Orioles at Oriole Park at Camden Yards. Mandatory Credit: James A. Pittman-Imagn Images

Boston Red Sox News

Jun 24, 2024; Boston, Massachusetts, USA; Boston Red Sox shortstop Ceddanne Rafaela (43) is tagged out by Toronto Blue Jays shortstop Isiah Kiner-Falefa (7) during the third inning at Fenway Park. Mandatory Credit: Paul Rutherford-Imagn Images

Boston Red Sox News

Oct 13, 2025; Toronto, Ontario, CAN; Toronto Blue Jays infielder Isiah Kiner-Falefa (7) takes batting practice before game two of the ALCS round against the Seattle Mariners for the 2025 MLB playoffs at Rogers Centre. Mandatory Credit: Nick Turchiaro-Imagn Images

Boston Red Sox News

New Boston Red Sox infielder Isiah Kiner-Falefa serves as a key insurance policy.

Oct 23, 2025; Toronto, ON, Canada; Toronto Blue Jays infielder Isiah Kiner-Falefa (7) responds to a question during media day before game one of the World Series at Rogers Centre. Mandatory Credit: John E. Sokolowski-Imagn Images

Boston Red Sox News

The Boston Red Sox and infielder Isiah Kiner-Falefa reportedly agreed to a $6 million salary for the coming season.

Sep 7, 2025; Phoenix, Arizona, USA; Boston Red Sox third baseman Alex Bregman against the Arizona Diamondbacks at Chase Field. Mandatory Credit: Mark J. Rebilas-Imagn Images

Boston Red Sox News

Did the Boston Red Sox make a fatal mistake this offseason? Perhaps one which would be considered somewhat familiar?

Oct 28, 2025; Los Angeles, California, USA; Toronto Blue Jays shortstop Isiah Kiner-Falefa (7) speaks in a press conference before game four of the 2025 MLB World Series against the Los Angeles Dodgers at Dodger Stadium. Mandatory Credit: Kirby Lee-Imagn Images

Boston Red Sox News

The Boston Red Sox may have closed some doors on Wednesday night.

Sep 16, 2025; Pittsburgh, Pennsylvania, USA; Chicago Cubs second baseman Nico Hoerner (2) looks on at he batting cage before the game against the Pittsburgh Pirates at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images

Boston Red Sox News

It may not be the most likely outcome, but a blockbuster trade remains on the table for the Boston Red Sox.

Sep 28, 2024; Boston, Massachusetts, USA; Boston Red Sox catcher Mickey Gasper (77) walks off of the field after striking out against the Tampa Bay Rays during the sixth inning at Fenway Park. Mandatory Credit: Brian Fluharty-Imagn Images

Boston Red Sox News

On Wednesday, the Boston Red Sox claimed Gasper off waivers from the Washington Nationals, according to a team announcement.

Boston Red Sox News

Are the Boston Red Sox really going to make any more big trades this winter? That's what one beat reporter believes.

May 18, 2025; Arlington, Texas, USA; Houston Astros third base Isaac Paredes (15) rounds the bases after hitting a three run home run during the eighth inning against the Texas Rangers at Globe Life Field. Mandatory Credit: Tim Heitman-Imagn Images

Boston Red Sox News

The Boston Red Sox and Houston Astros are both obvious and imperfect potential trade partners.

Apr 20, 2025; Boston, Massachusetts, USA; Fans line the field in front of the Green Monster as the Chicago White Sox warm up before a game at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images

Boston Red Sox News

The Boston Red Sox have to be ecstatic about where shortstop Franklin Arias' development is headed.

Sep 7, 2025; Phoenix, Arizona, USA; Boston Red Sox pitcher Aroldis Chapman in the ninth inning against the Arizona Diamondbacks at Chase Field. Mandatory Credit: Mark J. Rebilas-Imagn Images

Boston Red Sox News

The Boston Red Sox learned Tuesday that Aroldis Chapman won't pitch in the World Baseball Classic.

Apr 27, 2025; Kansas City, Missouri, USA; Houston Astros hat and glove in the dugout during the second inning against the Kansas City Royals at Kauffman Stadium. Mandatory Credit: William Purnell-Imagn Images

Boston Red Sox News

No one believes that the Houston Astros wouldn't trade a certain infielder to the Boston Red Sox if given the chance.

Sep 27, 2025; Washington, District of Columbia, USA; Washington Nationals shortstop CJ Abrams (5) fields a ground ball by Chicago White Sox shortstop Chase Meidroth (not pictured) during the first inning at Nationals Park. Mandatory Credit: Geoff Burke-Imagn Images

Boston Red Sox News

Are the Boston Red Sox going to make a trade with the Washington Nationals? That's what Steve Phillips wants to see.