Alex Bregman: Detroit Tigers or Boston Red Sox? Insider insight from Red Sox broadcaster Will Flemming

The Winter Meetings are underway in Orlando, and the Detroit Tigers arrive with several storylines to follow. On "Days of Roar," Evan Petzold and Chris Brown discuss the signing of right-hander Drew Anderson to a one-year contract. He will show up to spring training as a starter, but will he ultimately become a reliever? We break down what to watch with the Tigers at the Winter Meetings, including big updates on Alex Bregman's free agency and Tarik Skubal's trade situation. Other topics about the Tigers include the pursuit of another starter for the rotation and the remaining high-leverage relievers to upgrade the bullpen. Boston Red Sox radio voice Will Flemming joins the show to discuss Bregman's market, his impact in Boston's clubhouse in 2025 and whether a reunion with the Red Sox is the most likely outcome. He also endorses an all-in Skubal trade for the Red Sox, even though Skubal is set to become a free agent after the 2026 season. To wrap up, Evan and Chris provide — and break down — mock trades for Skubal with the Red Sox, Los Angeles Dodgers, New York Mets, Baltimore Orioles and New York Yankees. Follow Evan on X/Twitter here. Read Evan's most recent work here