The 2026 World Series brings together two clubs built on pitching and small-ball in the Brewers and Rays, and for Red Sox fans, there’s a familiar thread running through both rosters. Four former Boston players are now on the sport’s biggest stage: two with Tampa Bay, two with Milwaukee.
Cam Booser is one of the Rays’ bullpen weapons. Boston originally took a chance on him in 2023 after his time in the Twins organization, a retirement, and stops in independent ball.
He earned a spring training invite in 2024, cracked the Red Sox roster, and finished that season with a 3.38 ERA and 43 strikeouts in 43 relief appearances before being traded to the White Sox that offseason. After the 2025 season, he signed with Tampa Bay on a minor-league deal, and the move paid off in a big way.
In 2026, Booser made 42 appearances, posted a 1.98 ERA, struck out 45, and became one of Kevin Cash’s most trusted relievers. He has also stayed one of the Rays’ key bullpen options in the postseason.
Steven Matz followed a different path from Boston to Tampa Bay. The left-hander arrived in July 2025 in a trade with the Mets that sent Blaze Jordan to New York, then worked as a reliever for the Red Sox and gave them 21 appearances, a 2.08 ERA, 12 strikeouts and one save over 21.2 innings.
He left for the Rays last offseason on a two-year, $15 million deal and opened the year as a starter. That didn’t stick.
After a 5.48 ERA in his first 10 starts, Tampa Bay shifted him to the bullpen. He has settled in some since then, but he hasn’t locked down a top relief role.
Milwaukee’s side features David Hamilton, a player the Brewers originally drafted in the 2019 MLB Draft before Boston got him in the December 2021 Hunter Renfroe trade, which also brought Jackie Bradley Jr. and Alex Binelas to the Red Sox. Hamilton reached the majors for the first time in June 2022 and moved back and forth between Boston and Triple-A that season.
His speed and defense have long stood out, and he followed that with 33 steals in 2024 and 22 in 2025. Boston later sent him back to his original organization in an offseason deal that sent Hamilton, Kyle Harrison and Shane Drohan to Milwaukee for Caleb Durbin, Andruw Monasterio, Anthony Seigler and a compensation pick.
Hamilton has been a strong fit for the Brewers in 2026, swiping 30 bases and even homering off Edwin Diaz in the NLCS.
Kyle Harrison is the other former Red Sox arm now with Milwaukee. He was part of the June 2025 Rafael Devers blockbuster and spent only a few months in Boston, making three appearances with a 3.00 ERA and 13 strikeouts in 12 innings.
Boston moved on from him last offseason, and he landed in the Brewers’ rotation. In 2025, Harrison started 28 games, went 11-5, and posted a 4.20 ERA with 141 strikeouts.
In Other News...
Red Sox Face A Serious Problem In Their Search For Power
Power was already near the top of Bostons offseason shopping list, and it looks like the Red Sox may have to shop carefully if they want to add it. Randy Arozarena fits the kind of bat they need, with a track record of strong offense and a preference for playing on the East Coast, which at least gives Boston a plausible opening as he heads toward free agency after his time with the Mariners.
The problem, of course, is that the market figures to be crowded. Arozarena is expected to draw interest from several clubs, including the Yankees, Mets, Phillies and Cubs, which means the Red Sox would not be bidding in a quiet corner of the winter. For a team trying to add more consistent punch, the question may not be whether he makes sense, but whether Boston can win a race that figures to get expensive fast. [Read more 🡒]
Red Sox Could Enter The Chase For A Fascinating Power Bat
A power bat with real track record in Japan has become available on the market, and that is the kind of profile the Red Sox have reason to watch closely. Teruaki Sato, the Hanshin Tigers slugger, has drawn interest from multiple MLB teams after being posted for big-league clubs to pursue this offseason, giving the market a notable name for clubs looking to add pop.
For Boston, the fit is easy to see. The Red Sox have been searching for ways to deepen their lineup with more thump, and Sato checks the box as a potential power-hitting addition who could appeal if the club decides to press into that chase. Nothing is finalized yet, but with several teams already sniffing around, the early part of this winter could decide how aggressive Boston wants to be. [Read more 🡒]
Red Sox Face An Offseason Decision That Could Define 2027
The Red Sox have spent the last two Octobers learning how thin the margin can be, making the playoffs in back-to-back seasons only to get pushed out quickly each time, including a sweep at the hands of the Yankees in 2026. Injury trouble only made the picture murkier, with key players like Garrett Crochet, Roman Anthony and Willson Contreras all dealing with setbacks during the season, leaving Boston to patch together its roster and keep pace in a tight race.
Now the focus shifts to 2027, where the organization will need healthier returns from that group just to stabilize the core. At the same time, the front office is staring at a crowded outfield and a number of contract commitments, which means the next round of roster decisions may not just shape the bench or the depth chart, but define the shape of the team for the next run. [Read more 🡒]