On the final day of the Winter Meetings, Chuck Garfien closes things out with a loaded lineup of conversations. He starts with White Sox GM Chris Getz, diving into the outfielder market and how the Sox are approaching it. Chuck then chats with MLB.com draft expert Jonathan Mayo for an early read on the 2026 draft class. MassLive.com’s Sean McAdam stops by to give the latest on the Red Sox’s interest in White Sox catcher Kyle Teel. And wrapping things up, Chuck checks in with agent Scott Boras to get his perspective on Luis Robert Jr.’s 2026 outlook.

The White Sox win the Draft Lottery! Chuck Garfien reacts to the White Sox landing the No. 1 overall pick in the 2026 MLB Draft. He speaks with GM Chris Getz about how securing the top selection reshapes the organization’s long-term plans. Chuck then catches up with White Sox scouting director Mike Shirley, who breaks down what this opportunity means for their draft strategy and the type of player the Sox could target. Finally, Chuck sits down with Hall of Famer and former No. 1 overall pick Harold Baines, the White Sox’s draft lottery representative, who shares his own draft experience. 

Chuck Garfien checks in from the MLB Winter Meetings in Orlando, where he’s on site all week getting the inside scoop on the White Sox. He asks GM Chris Getz for the latest on Luis Robert Jr. Chuck then catches up with manager Will Venable, who shares what the young and confident Sox are telling him about their expectations for next season and how he’s looking to grow following his first year at the helm. Finally, Chuck chats with ’05 World Series champion and “Foul Territory” co-host A.J. Pierzynski, who gives his thoughts on why the White Sox should pursue slugger Kyle Schwarber.

Chuck Garfien is joined by MLB.com’s White Sox beat writer Scott Merkin for a deep dive into the biggest storylines of the Sox offseason. Chuck puts Scott on the spot with 10 Burning Questions—from what the White Sox might do at the Winter Meetings to who will be playing first base, third base, and right field on Opening Day 2026. They discuss potential additions to the rotation, whether the Sox will pursue a closer, which players could be on the trade block, and if Luis Robert Jr. is on the move, who would take his spot in center field. Chuck and Scott also look at how the new pitching and hitting coaches could shape the team’s future and evaluate the chances the Sox can push toward a .500 season in 2026.

Chuck Garfien is joined by White Sox reporters Connor McKnight and Brooke Fletcher for a wide-ranging look at the White Sox offseason, breaking down the team’s latest roster moves following the non-tender deadline. They dig into which free agents could fit the Sox’s needs, from infield help to pitching, and what type of veteran leader might make sense. The trio makes bold predictions and discusses the possibility of trades involving Luis Robert Jr., Kyle Teel, or Edgar Quero. Chuck and company also try to predict where the White Sox will be selecting in the MLB Draft with a little help from Tankathon.

Chuck Garfien sits down with rising White Sox prospect Sam Antonacci, who capped off a strong season with an impressive showing in the Arizona Fall League. Antonacci discusses his development, the work he’s focusing on this offseason, and what he learned playing alongside several other Sox prospects. He also reflects on his path from community college to the White Sox system, his competitive style, and why he takes pride in doing the little things well.

Chuck Garfien sits down with new White Sox hitting coach Derek Shomon to discuss his approach and what he brings to the White Sox lineup. Shomon talks about building relentless at-bats, practicing game-like situations, and preparing hitters for any situation at the plate. He shares takeaways from Minnesota and Miami, thoughts on Luis Robert Jr. and Colson Montgomery, and building on the success of Lenyn Sosa. Shomon also reflects on returning home and what it means to be closer to family.

New White Sox pitching coach Zach Bove joins Chuck Garfien for his first conversation since taking the job. Bove lays out his individual approach to pitcher development, what he learned from Kansas City’s rise, and how he plans to make the Sox better on the mound. He explains his thoughts on using openers, why a designated closer isn’t mandatory, and how he'll approach the 2026 rotation.

White Sox prospect George Wolkow joins Chuck Garfien in studio to look back on his 2025 season. He discusses how discipline and swing decisions are the focus this offseason, what he learned from watching Colson Montgomery’s journey, and how meeting with Bo Jackson fueled his outlook. Also, the story behind his one-handed RBI, being mic’d up for Top Prospects, and why he believes mindset is the key on the road to Chicago.

White Sox pitching prospect stand-out Hagen Smith joins Chuck Garfien from the Arizona Fall League to reflect on his 2025 season. They discuss early arm soreness, mechanical tweaks, and dominating in the Birmingham Barons’ championship run. Smith opens up on what he learned through adversity, why slowing things down changed everything, and how the Arizona Fall League is helping shape his approach for 2026.