Boston Red Sox offseason strategy takes center stage as the Winter Meetings approach. Could relief pitcher Devin Williams be the steal of free agency despite his rough Yankees stint?

Host Gabby (Hurlbut) Maljanian breaks down why Williams' projected $5.7 million contract represents low-risk, high-reward potential after his 1.83 ERA across six Brewers seasons. The analysis covers the critical importance of re-signing Alex Bregman, whose second-half struggles stemmed from carrying the lineup alone after Rafael Devers' departure. Key discussion points include adding a second power bat—Pete Alonso or Kyle Schwarber, who crushed 56 home runs in 2025—to transform Boston's offense into a championship contender.

The episode examines how Craig Breslow's front office can build a super bullpen around Aroldis Chapman and Garrett Whitlock, plus a 2026 schedule preview featuring early tests against the Reds, Astros, Padres, and Yankees that will reveal whether the Red Sox made sufficient improvements.

Discover which moves could vault Boston back into World Series contention and why the next few weeks will define their 2026 season.

Support Us By Supporting Our Sponsors!

Gametime
Download the Gametime app, create an account, and use code LOCKEDONMLB for $20 off your first purchase. Terms apply. Download Gametime today. What time is it? Gametime.

FanDuel
Today's episode is brought to you by FanDuel. The NBA and NFL seasons are here, visit the FanDuel App today and start planning your futures bets now.

FANDUEL DISCLAIMER: 21+ in select states. First online real money wager only. Bonus issued as nonwithdrawable free bets that expires in 14 days. Restrictions apply. See terms at sportsbook.fanduel.com. Gambling Problem? Call 1-800-GAMBLER or visit FanDuel.com/RG (CO, IA, MD, MI, NJ, PA, IL, VA, WV), 1-800-NEXT-STEP or text NEXTSTEP to 53342 (AZ), 1-888-789-7777 or visit ccpg.org/chat (CT), 1-800-9-WITH-IT (IN), 1-800-522-4700 (WY, KS) or visit ksgamblinghelp.com (KS), 1-877-770-STOP (LA), 1-877-8-HOPENY or text HOPENY (467369) (NY), TN REDLINE 1-800-889-9789 (TN)