Lucas Giolito attendance at World Series can help Red Sox massively in free agency

World Series - New York Yankees v Los Angeles Dodgers - Game 1
World Series - New York Yankees v Los Angeles Dodgers - Game 1 / Harry How/GettyImages

The stars were out at Game 1 of the 120th World Series at Dodger Stadium on Oct. 25, including Boston Red Sox pitcher Lucas Giolito and his former high school baseball teammate, Max Fried.

Giolito and Fried attended the series-opening game to support another former Harvard-Westlake player — Jack Flaherty. The three pitchers are well acquainted from their years as high school baseball teammates in their native California, about 20 miles west of Dodger Stadium.

The three players have supported each other in major league-career-defining moments before. Giolito and Flaherty attended Fried's final start in the 2021 World Series, when he posted six shutout innings to carry the Braves to victory over the Astros.

Fried and the Braves were eliminated early in the 2024 postseason in the Wild Card round, and Giolito quickly began recruiting his former teammate to join the Red Sox in 2025. There's no telling if Giolito has any pull with his former teammates until they sign somewhere, but if he does, Fried and Flaherty both have links to the Sox. They could both fill the veteran starter role Boston is desperate for.

Lucas Giolito gives Red Sox a connection to impending free agent pitchers Max Fried and Jack Flaherty

Fried may be the more ideal fit for Boston of Giolito's two high school teammates. His left-handedness would bring more diversity and balance to the Red Sox's rotation, which comprised all righties in 2024. Fried posted a 3.25 ERA with a 1.16 WHIP and 166 strikeouts over 174.1 innings this season. The 30-year-old has spent all eight seasons of his career with Atlanta, and clocked a 3.07 ERA in that time.

Flaherty is a righty, but he could still be a solid fit for the Red Sox's rotation. He logged a 3.17 ERA with a 1.07 WHIP, 194 strikeouts and 38 walks over 162 innings in 2024. He's been less consistent in his career than Fried — he posted a 4.99 ERA in 2023 and a 3.63 over his eight-year career

Fried and Flaherty will be among the most highly-coveted pitchers of this winter's free agent class, especially if Flaherty can maintain his success from Game 1 of the World Series. Hopefully, Giolito will have some influence on where the two hurlers will sign.

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