{"id":835880,"date":"2026-10-23T10:42:23","date_gmt":"2026-10-23T10:42:23","guid":{"rendered":"https:\/\/www.rawchili.com\/mlb\/835880\/"},"modified":"2026-10-23T10:42:23","modified_gmt":"2026-10-23T10:42:23","slug":"all-the-ex-red-sox-to-watch-in-this-historic-2026-world-series","status":"publish","type":"post","link":"https:\/\/www.rawchili.com\/mlb\/835880\/","title":{"rendered":"All the ex-Red Sox to watch in this historic 2026 World Series"},"content":{"rendered":"

The Red Sox may have been a first-round exit this postseason, but several of their former players are about to face off in an historic World Series that is guaranteed to end with a team winning its first-ever championship.<\/p>\n

On the American League side, the formidable Tampa Bay Rays pitching staff includes relievers Cam Booser and Steven Matz.<\/p>\n

Booser was the feel-good story<\/a> of the 2024 Red Sox. He walked away from baseball after toiling in the Minnesota Twins organization for five years, joined a carpenters\u2019 union and became a construction worker. Then, he began giving baseball lessons and discovered he could throw a high-90s fastball, and embarked on a second pro-ball odyssey. He pitched in semi-pro and independent leagues until the Twins granted his release, which enabled him to sign with the Arizona Diamondbacks.<\/p>\n

After the Diamondbacks released Booser in July 2022, he signed with the team he rooted for as a child, and Booser excelled with Triple-A Worcester in 2023. After battling alcoholism and injuries that included broken vertebrae in high school and Tommy John surgery in college, Booser finally made his big-league debut<\/a> at 31 years old against the Pittsburgh Pirates on April 19, 2024. At season\u2019s end, he was honored as the recipient of the 2024 Tony Conigliaro Award, given annually to a \u201cMajor Leaguer who has overcome adversity through the attributes of spirit, determination and courage.\u201d<\/p>\n

The Red Sox traded Booser to the White Sox after the 2024 season, and he signed a minor league contract with the Rays last January after being non-tendered by Chicago. He posted a career-best 1.98 ERA over 42 regular-season appearances for Tampa Bay this year, with a career-high 45 strikeouts in 41 innings. In his first postseason, Booser owns a 0.00 ERA over six appearances, with a hit, walk and two strikeouts over 4 2\/3 innings.<\/p>\n

Matz was the most productive of Boston\u2019s additions at the 2025 trade deadline. Acquired from the St. Louis Cardinals, he pitched to a 2.08 ERA over 21 regular-season games and made two scoreless appearances in the wild card series. Matz then signed a two-year, $15 million free-agent deal with the Rays last winter. The 12-year MLB veteran pitched to his worst regular-season ERA (5.49) since 2020, but his lone appearance so far this October was two perfect innings in Game 3 of the American League Championship Series.<\/p>\n

\"TampaTampa Bay Rays pitcher Cam Booser throws against the Cleveland Guardians during the seventh inning in Game 6 of an American League Championship Series in St. Petersburg, Fla. Monday, Oct. 19, 2026. (AP Photo\/David J. Phillip)<\/p>\n

The Milwaukee Brewers\u2019 roster is even more Sox-centric with infielder David Hamilton, rookie left-hander Shane Drohan, veteran righty Dustin May and southpaw Kyle Harrison. Milwaukee\u2019s star catcher William Contreras is also the brother of Red Sox first baseman Willson Contreras.<\/p>\n

The Red Sox traded Harrison, Hamilton, and Drohan to Milwaukee for infielders Caleb Durbin, Andruw Monasterio and Anthony Seigler during the first week of spring training last February.<\/p>\n

Hamilton has been stellar so far in his first career postseason run. Over four games between the NLDS and NLCS, he was 5 for 11 (.455) with a home run, five runs scored, two RBI, three stolen bases and two strikeouts. Hamilton played a crucial role in the Brewers\u2019 sweep of the Dodgers in the NLCS, going 2 for 3 with two stolen bases and three runs scored in Game 2.<\/p>\n

Drohan, Boston\u2019s fifth-round pick in 2020, made his postseason debut as the Brewers\u2019 opener for Game 4 of the NLCS. The 27-year-old southpaw made his big-league debut with the Brewers on April 8, and pitched to a 4.19 ERA over 33 regular-season games, including 19 starts, struck out 125 batters and issued 44 walks in 124 2\/3 innings.<\/p>\n

May\u2019s Red Sox tenure was short and sour. Acquired from the Los Angeles Dodgers at the 2025 trade deadline<\/a>, he pitched to a 5.40 ERA over six regular-season games before going on the injured list in early September.<\/p>\n

The Cardinals signed May to a one-year contract last December, and dealt him to the Brewers at this summer\u2019s deadline. He posted a 5.65 ERA over 10 starts for Milwaukee in the regular season, and has allowed multiple runs in two of his three postseason games thus far.<\/p>\n

Harrison was on the Brewers\u2019 NLDS and NLCS rosters, but has yet to pitch in a postseason game.<\/p>\n

Last, but certainly not least, is a current Red Sox star who will be on hand to entertain the masses in a new way. Effervescent rookie left-hander Payton Tolle is one of Major League Baseball\u2019s player-correspondents for the Fall Classic, the league announced Thursday.<\/p>\n

The Brewers were founded in 1970, after one season as the Seattle Pilots. This will be their second trip to the championship round, and first since switching over to the National League in 1998. They fell to the St. Louis Cardinals, now their division opponents, in seven games in the 1982 Fall Classic.<\/p>\n

The Rays are the newest of the five trophy-less teams, incepted in 1998. This is their third World Series appearance, following losses to the Phillies in 2008 and Dodgers in 2020.<\/p>\n

The 122nd World Series begins Friday at 8 p.m. ET on FOX Sports.<\/p>\n

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