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 Milwaukee Brewers On SI please reach out to Scott Neville: scott@wtfsports.org

Milwaukee Brewers pitcher Freddy Peralta (51) pitches during the first inning of the National League Division Series game against the Chicago Cubs on Saturday October 4, 2025 at American Family Field in Milwaukee, Wisconsin.

Aug 21, 2025; Chicago, Illinois, USA; Milwaukee Brewers second baseman Brice Turang (2) celebrates with teammates in the dugout after hitting a two-run home run against the Chicago Cubs during the second inning at Wrigley Field. Mandatory Credit: Kamil Krzaczynski-Imagn Images

Yount and former teammate Paul Molitor during the 1982 World Series against the St. Louis Cardinals.

1994 Press Photo Brewers Robin Yount Talks With Former Teammate Paul Molitor

Jul 6, 2025; Denver, Colorado, USA; General view of a players cap and glove of the Colorado Rockies during the ninth inning against the Chicago White Sox at Coors Field. Mandatory Credit: Ron Chenoy-Imagn Images

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The Milwaukee Brewers' outfield depth chart is in good shape, but one minor leaguer did bolt for the Colorado Rockies recently.

Sep 26, 2025; Toronto, Ontario, CAN; The hat and glove of Tampa Bay Rays third baseman Junior Caminero (13) in the dugout during the game against the Toronto Blue Jays at Rogers Centre. Mandatory Credit: John E. Sokolowski-Imagn Images

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The Milwaukee Brewers saw some Triple-A depth depart at the end of November, as the Tampa Bay Rays took an interest in Raynel Delgado.

Jun 27, 2025; Milwaukee, Wisconsin, USA; Milwaukee Brewers pitcher Freddy Peralta (51) enjoys a moment during the first inning against the Colorado Rockies at American Family Field. Mandatory Credit: Jeff Hanisch-Imagn Images

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Milwaukee Brewers fans who don't want Freddy Peralta traded got some good news on Monday.

May 23, 2025; Pittsburgh, Pennsylvania, USA; Milwaukee Brewers starting pitcher Freddy Peralta (51) delivers a pitch against the Pittsburgh Pirates during the first inning at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images

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Are the Milwaukee Brewers going to deal Freddy Peralta for a two-player package?

Sep 20, 2025; Cincinnati, Ohio, USA; Chicago player hats are seen on the dugout steps during the game between the Chicago Cubs and the Cincinnati Reds at Great American Ball Park. Mandatory Credit: Aaron Doster-Imagn Images

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What will the Milwaukee Brewers accomplish on the open market this winter? Here's one baseball expert's guess.

Aug 17, 2024; Milwaukee, Wisconsin, USA; Milwaukee Brewers starting pitcher Freddy Peralta (51) reacts after striking out Cleveland Guardians first baseman Josh Naylor (22) in the sixth inning at American Family Field. Mandatory Credit: Benny Sieu-Imagn Images

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The Milwaukee Brewers should not give up Freddy Peralta for a package of only two unproven players.

Sep 24, 2025; San Diego, California, USA; Milwaukee Brewers left fielder Jake Bauers (9) hits a double during the second inning against the San Diego Padres at Petco Park. Mandatory Credit: Denis Poroy-Imagn Images

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The Milwaukee Brewers have Jake Bauers back under contract for 2026 in what could very well be his last season with the club.

Aug 25, 2025; Milwaukee, Wisconsin, USA; Milwaukee Brewers pitcher Brandon Woodruff (53) delivers a pitch abasing the Arizona Diamondbacks in the first inning at American Family Field. Mandatory Credit: Mark Hoffman/USA Today Network via Imagn Images

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Brandon Woodruff says he's about to embark on a relatively normal offseason, and that should be music to Milwaukee Brewers fans' ears.

Jun 11, 2021; Milwaukee, Wisconsin, USA; Milwaukee Brewers pitcher Brandon Woodruff (53) looks in for the sign during the first inning against the Pittsburgh Pirates at American Family Field. Mandatory Credit: Jeff Hanisch-Imagn Images

The Milwaukee Brewers likely weren't counting on Brandon Woodruff accepting his qualifying offer... but he did.

Jun 27, 2025; Milwaukee, Wisconsin, USA; Milwaukee Brewers pitcher Freddy Peralta (51) enjoys a moment during the first inning against the Colorado Rockies at American Family Field. Mandatory Credit: Jeff Hanisch-Imagn Images

The Milwaukee Brewers may privately see Brandon Woodruff's accepted qualifying offer as reason to trade Freddy Peralta, but won't say so publicly.

May 18, 2025; Milwaukee, Wisconsin, USA; Milwaukee Brewers pitcher Freddy Peralta (51) delivers a pitch in the first inning against the Minnesota Twins at American Family Field. Mandatory Credit: Michael McLoone-Imagn Images

The Milwaukee Brewers might trade Freddy Peralta, or they might not. Here's one important determining factor, per an insider.

Are the Milwaukee Brewers willing to risk losing this talented righty?