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

Jun 5, 2026; Bronx, New York, USA; Boston Red Sox first baseman Willson Contreras (40) reacts after an RBI single during the third inning against the New York Yankees at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images

Boston Red Sox News

May 26, 2026; Boston, Massachusetts, USA; Atlanta Braves pitcher Spencer Strider (99) on the mound against the Boston Red Sox in the first inning at Fenway Park. Mandatory Credit: David Butler II-Imagn Images

Boston Red Sox News

Jun 3, 2026; Milwaukee, Wisconsin, USA; San Francisco Giants first baseman Rafael Devers (16) looks around after striking out during the first inning against the Milwaukee Brewers at American Family Field. Mandatory Credit: Jeff Hanisch-Imagn Images

Boston Red Sox News

Jun 13, 2026; Minneapolis, Minnesota, USA; St. Louis Cardinals third baseman Blaze Jordan (33) celebrates his run against the Minnesota Twins in the second inning at Target Field. Mandatory Credit: Bruce Kluckhohn-Imagn Images

Boston Red Sox News

Jun 13, 2026; Boston, Massachusetts, USA; Boston Red Sox pitcher Aroldis Chapman (44) and catcher Carlos Narváez (75) smile after defeating the Texas Rangers at Fenway Park. Mandatory Credit: Bob DeChiara-Imagn Images

Boston Red Sox News

The Boston Red Sox hadn't won a home series since April.

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

Boston Red Sox fans may not be focused on the draft, but it's coming soon regardless.

Apr 13, 2026; Minneapolis, Minnesota, USA; Boston Red Sox starting pitcher Garrett Crochet (35) delivers a pitch against the Minnesota Twins in the first inning at Target Field. Mandatory Credit: Jesse Johnson-Imagn Images

Boston Red Sox News

The Boston Red Sox know a trade deadline sell-off could be coming. Maybe they don't want to worry too much about it?

Jun 5, 2026; Bronx, New York, USA; Boston Red Sox first baseman Willson Contreras (40) hits a two run home run during the fifth inning against the New York Yankees at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images

Boston Red Sox News

The Boston Red Sox absolutely should not trade Willson Contreras.

May 17, 2026; Cumberland, Georgia, USA; Boston Red Sox catcher Connor Wong (12) celebrates scoring a run against the Atlanta Braves during the ninth inning at Truist Park. Mandatory Credit: Jordan Godfree-Imagn Images

Boston Red Sox News

Boston Red Sox catcher Connor Wong told it like it was when reflecting on the results of two infamous trades.

Jun 8, 2026; St. Petersburg, Florida, USA; Boston Red Sox third baseman Caleb Durbin (5) mishandles a ground ball in the sixth inning against the Tampa Bay Rays at Tropicana Field. Mandatory Credit: Jonathan Dyer-Imagn Images

Boston Red Sox News

The Boston Red Sox and all baseball fans should know that a trade can't be judged a month and a half in.

Feb 22, 2026; Peoria, Arizona, USA; Los Angeles Dodgers base runner James Tibbs III dives back to first base on a pickoff attempt against the San Diego Padres during a spring training game at Peoria Sports Complex. Mandatory Credit: Mark J. Rebilas-Imagn Images

Boston Red Sox News

Why can't the Boston Red Sox seemingly ever win a trade these days?

May 20, 2026; Kansas City, Missouri, USA; Boston Red Sox catcher Carlos Narvaez (75) bats during the eighth inning against the Kansas City Royals at Kauffman Stadium. Mandatory Credit: Jay Biggerstaff-Imagn Images

Boston Red Sox News

The Boston Red Sox's expected starting catcher hasn't lived up to his end of the bargain.

May 17, 2026; Cumberland, Georgia, USA; Boston Red Sox second baseman Marcelo Mayer (11) runs to the dugout after the end of the inning against the Atlanta Braves during the third inning at Truist Park. Mandatory Credit: Jordan Godfree-Imagn Images

Boston Red Sox News

Marcelo Mayer wasn't traded to the Arizona Diamondbacks. But that didn't mean everyone always believed it.

May 4, 2026; Detroit, Michigan, USA; Boston Red Sox pitcher Garrett Whitlock (22) pitches in the eighth inning against the Detroit Tigers at Comerica Park. Mandatory Credit: Rick Osentoski-Imagn Images

Boston Red Sox News

The Boston Red Sox have some players with very interesting storylines about to play out.

Jun 5, 2026; Bronx, New York, USA; Boston Red Sox first baseman Willson Contreras (40) looks out while wearing a playable weekend patch on his cap during the seventh inning against the New York Yankees at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images

Boston Red Sox News

The rest of the Boston Red Sox need to be a bit more like Willson Contreras, consistently.

Apr 24, 2026; Baltimore, Maryland, USA; Boston Red Sox pitcher Brayan Bello (66) delivers during the third inning against the Baltimore Orioles at Oriole Park at Camden Yards. Mandatory Credit: Mitch Stringer-Imagn Images

Boston Red Sox News

The Boston Red Sox just demoted Brayan Bello, and their reasoning had layers to it.