What are the Brewers' 2027 Plans: Contreras, Ashby & Free Agency | Rays Fallout, MLB Awards

The Milwaukee Brewers are World Series champions. Now comes the challenge of defending their title.

Derek VanRiper and Eno Sarris look ahead to the Brewers' 2027 season, examining William Contreras' future in Milwaukee, Aaron Ashby's potential move to the starting rotation and the offseason decisions facing the reigning World Series champions.

Could Milwaukee bring back its championship core? What happens with Brandon Woodruff, JoJo Romero and Jake Bauers? And how will one of baseball's strongest farm systems help the Brewers build another contender?

Plus, Closing the Tab on the Tampa Bay Rays. After a remarkable 2026 season ended in a World Series loss, DVR and Eno examine Tampa Bay's offensive limitations, pitching depth and potential offseason upgrades.

Finally, it's the Performance Review, sponsored by Sage. The guys make their 2026 MLB awards picks, including Yordan Alvarez vs. Bobby Witt Jr. for AL MVP, Pete Crow-Armstrong's historic NL MVP campaign and the Cy Young cases for Cam Schlittler and Jacob Misiorowski.

02:05 – Brewers World Series Afterglow 02:59 – Milwaukee Prepares for Its Championship Parade 07:25 – An Incredible Brewers Fan Story 09:29 – What's Next for the Brewers in 2027? 11:22 – William Contreras' Future in Milwaukee 15:10 – Contreras' Development and Long-Term Role 16:44 – Brandon Woodruff's Future 20:31 – Milwaukee's Farm System and Pitching Depth 24:24 – Could Aaron Ashby Return to the Rotation? 25:36 – JoJo Romero's Free Agency and Bullpen Decisions 26:48 – Pat Murphy's Message to Jake Bauers 30:14 – Closing the Tab: Tampa Bay Rays 31:29 – Tampa Bay's Offensive Limitations 32:40 – How Will New Ownership Shape the Rays? 36:51 – Tampa Bay's Pitching and Contract Decisions 39:01 – Potential Rays Trades and Roster Upgrades 42:21 – Performance Review: 2026 MLB Awards 42:45 – AL MVP: Yordan Alvarez vs. Bobby Witt Jr. 44:19 – NL MVP: Pete Crow-Armstrong's Historic Season 46:50 – AL & NL Cy Young Award Predictions 49:32 – What's Coming Next on Rates & Barrels?

Every weekday, Derek VanRiper and Eno Sarris explore Major League Baseball through analytics, player development, roster construction and the latest news from around the league.

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