Inside The Red Sox
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

Sep 1, 2020; Minneapolis, Minnesota, USA; A full moon rises over the Minnesota Twins logo in a game between the Minnesota Twins and Chicago White Sox at Target Field. Mandatory Credit: Brad Rempel-Imagn Images
Boston Red Sox News

Red Sox Projected Blockbuster Would Land $65 Million Twins Superstar In 4-Player Swap

Here's a Boston Red Sox trade that could land a new ace to pair with Garrett Crochet.

Jackson Roberts
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Oct 25, 2024; Los Angeles, California, USA; Los Angeles Dodgers outfielder Teoscar Hernandez (37) reacts on first after hitting a single in the seventh inning against the New York Yankees during game one of the 2024 MLB World Series at Dodger Stadium. Mandatory Credit: Kiyoshi Mio-Imagn Images
Boston Red Sox News

Red Sox Predicted To Nab $66 Million All-Star In 'Perfect' Free Agency Projection

The Boston Red Sox could be in line for a major power upgrade for the 2025 season.

Jackson Roberts
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Sep 25, 2024; Los Angeles, California, USA; San Diego Padres starting pitcher Dylan Cease (84) pitches in the first inning against the Los Angeles Dodgers at Dodger Stadium. Mandatory Credit: Kirby Lee-Imagn Images
Boston Red Sox News

Red Sox Blockbuster Trade Idea Lands Padres Ace Dylan Cease In 5-Player Swap

Should the Boston Red Sox consider trading multiple top position players for Dylan Cease?

Jackson Roberts
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Seattle Mariners logos help set the scene in the Seattle Terrace dining and shopping area of the Flight of Dreams complex in Japan. 636747024810893983-20-Seattle-Mariners-logos-help-set-the-scene-in-Seattle-Terrace-dining-and-shoppoig-area-of-the-Flight-of-Dreams-complex-in-Japan.-Photo-Harriet-Baskas.JPG
Boston Red Sox News

Red Sox Predicted To Acquire $72.5 Million Mariners All-Star In Blockbuster Trade

Could the Boston Red Sox nab a new ace starting pitcher from the Seattle Mariners?

Jackson Roberts
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Jul 16, 2024; Arlington, Texas, USA; National League pitcher Tanner Scott of the Miami Marlins (66) pitches in the eighth inning during the 2024 MLB All-Star game at Globe Life Field. Mandatory Credit: Kevin Jairaj-Imagn Images
Boston Red Sox News

Red Sox Predicted To Acquire $50+ Million All-Star In Free Agency Blockbuster

The Boston Red Sox could grab a marquee relief pitcher in free agency if this prediction comes true.

Jackson Roberts
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Oct 18, 2024; New York City, New York, USA; New York Mets first baseman Pete Alonso (20) reacts after being hit by a pitch during the fourth inning against the Los Angeles Dodgers during game five of the NLCS for the 2024 MLB playoffs at Citi Field. Mandatory Credit: Vincent Carchietta-Imagn Images
Boston Red Sox News

Red Sox Surprisingly Named Top Landing Spot For Mets $182 Million 4-Time All-Star

Should the Boston Red Sox make an unexpected play for this longtime New York Mets slugger?

Jackson Roberts
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May 24, 2023; Washington, District of Columbia, USA; San Diego Padres hats in the dugout during the game against the Washington Nationals at Nationals Park. Mandatory Credit: Brad Mills-Imagn Images
Boston Red Sox News

Red Sox Blockbuster Trade Idea Lands Padres $13 Million Superstar In 5-Player Swap

Would this trade work out for both the Boston Red Sox and San Diego Padres?

Jackson Roberts
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May 16, 2023; Boston, Massachusetts, USA; Seattle Mariners starting pitcher Luis Castillo (58) pitches during the first inning against the Boston Red Sox at Fenway Park. Mandatory Credit: Bob DeChiara-Imagn Images
Boston Red Sox News

Red Sox Mock Blockbuster Lands Mariners 3-Time All-Star Without Moving Triston Casas

Should the Boston Red Sox make a power play for this righty ace?

Jackson Roberts
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Sep 20, 2019; St. Petersburg, FL, USA; A detail view of Boston Red Sox hats and gloves at Tropicana Field. Mandatory Credit: Kim Klement-Imagn Images
Boston Red Sox News

Red Sox Projected As 'Best Fit' For $66 Million Dodgers Superstar Free Agent

Could this superstar free agent find a home in Boston?

Jackson Roberts
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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

Red Sox Expected To Make 'Very Serious' Push To Sign 23-Year-Old Japanese Superstar

The Boston Red Sox have an outside chance at landing a superstar pitcher for the next six seasons.

Jackson Roberts
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Jul 16, 2024; Arlington, Texas, USA; American League right fielder Anthony Santander of the Baltimore Orioles (25) hits single in the fifth inning during the 2024 MLB All-Star game at Globe Life Field. Mandatory Credit: Tim Heitman-Imagn Images
Boston Red Sox News

Red Sox Predicted To Sign 44-HR All-Star Slugger Amid Collapsing Free Agency Market

Should the Boston Red Sox wait out the market for a top free-agent slugger?

Jackson Roberts
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Mar 9, 2021; West Palm Beach, Florida, USA; A general view of the Houston Astros logo statue outside of The Ballpark of the Palm Beaches prior to the spring training game between the Houston Astros and the Washington Nationals. Mandatory Credit: Jasen Vinlove-Imagn Images
Boston Red Sox News

Red Sox Blockbuster Trade Idea Brings $19 Million Astros 2-Time All-Star To Boston

The Boston Red Sox could bring a new All-Star contributor to the pitching staff if this trade goes through.

Jackson Roberts
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