MLB Free Agent Predictions 2026/27 Edition

MLB's General Meetings wrapped up in Las Vegas as front offices prepare to make signings and trades before the Lockout deadline on December 1. For the White Sox, GM Chris Getz announced that reliever Grant Taylor is moving to the starting rotation. Why this plan could work, and what the concerns are about Taylor making this transition. Also, Will Venable wins American League Manager of the Year and shares what the honor means to him. Visit the NEW Sox Machine Store at SoxMachineShop.com to pick up your new White Sox and Sox Machine Gear. Sam Antonacci, Munetaka Murakami, Tristan Peters, Chase Meidroth, and the celibate-for-Sean Burke shirt! Plus new Sox Machine 3/4-zipup Sweaters, and Coffee Mugs. Officially licensed gear from the MLB Players Association. Visit SoxMachineShop.com Presented by ‪Ankin Law. Injury Law Made Personal.Shop Sox Machine Merch: https://soxmachineshop.com/See omnystudio.com/listener for privacy information.

Sox Machine's Josh Nelson and Jim Margalus predict where MLB's top 10 free agents will sign this offseason. Then they guess who will be the White Sox's biggest free-agent signing.  To get your new wireless plan for just 15 bucks a month, go to MintMobile.com/Territory. That’s it there’s no catch. Visit the NEW Sox Machine Store at SoxMachineShop.com to pick up your new White Sox and Sox Machine Gear. Sam Antonacci, Munetaka Murakami, Tristan Peters, Chase Meidroth, and the celibate-for-Sean Burke shirt! Plus new Sox Machine 3/4-zipup Sweaters, and Coffee Mugs. Officially licensed gear from the MLB Players Association. Visit SoxMachineShop.com Presented by  ⁨@HowardAnkin⁩ . Injury Law Made Personal.Shop Sox Machine Merch: https://soxmachineshop.com/See omnystudio.com/listener for privacy information.

Sox Machine's Josh Nelson shares his Offseason Plan Project for the Chicago White Sox. The challenge is how does this White Sox team keep the momentum they built in 2026? Who do they need to add to help fight off regression while staying below the $130 million payroll budget? Visit the NEW Sox Machine Store at SoxMachineShop.com to pick up your new White Sox and Sox Machine Gear. Sam Antonacci, Munetaka Murakami, Tristan Peters, Chase Meidroth, and the celibate-for-Sean Burke shirt! Plus new Sox Machine 3/4-zipup Sweaters, and Coffee Mugs. Officially licensed gear from the MLB Players Association. Visit SoxMachineShop.com Presented by Ankin Law‬. Injury Law Made PersonalShop Sox Machine Merch: https://soxmachineshop.com/See omnystudio.com/listener for privacy information.

MLB Free Agency officially begins, and it features an underwhelming hitters' class. Which five bats do Josh Nelson and Jim Margalus think are the best fits for the Chicago White Sox? Plus, Will Venable is a finalist for manager of the year, White Sox claim Graham Pauley, and eight players receive the Qualifying Offer. Visit the NEW Sox Machine Store at SoxMachineShop.com to pick up your new White Sox and Sox Machine Gear. Sam Antonacci, Munetaka Murakami, Tristan Peters, Chase Meidroth, and the celibate-for-Sean Burke shirt! Plus new Sox Machine 3/4-zipup Sweaters, and Coffee Mugs. Officially licensed gear from the MLB Players Association. Visit SoxMachineShop.com Presented by Ankin Law. Injury Law Made PersonalShop Sox Machine Merch: https://soxmachineshop.com/See omnystudio.com/listener for privacy information.

As Major League Baseball shifts into offseason mode, Sox Machine's Josh Nelson and Jim Margalus look at 5 potential free-agent targets to help the Chicago White Sox improve their rotation. Visit the NEW Sox Machine Store at SoxMachineShop.com to pick up your new White Sox and Sox Machine Gear. Sam Antonacci, Munetaka Murakami, Tristan Peters, Chase Meidroth, and the celibate-for-Sean Burke shirt! Plus new Sox Machine 3/4-zipup Sweaters, and Coffee Mugs. Officially licensed gear from the MLB Players Association. Visit SoxMachineShop.com Presented by Ankin Law - Injury Law Made PersonalShop Sox Machine Merch: https://soxmachineshop.com/See omnystudio.com/listener for privacy information.

Lots to catch up on as the Milwaukee Brewers won the 2026 World Series in five games. The Chicago White Sox hired Matt Roffe to lead MLB Draft efforts. The White Sox parted ways with John Schriffen, opening the TV play-by-play announcer role to an interesting list of candidates. The Chicago Sun-Times put a Chicago Bears stadium rendering in Bridgeport on its cover, but hours later Crain's Chicago reported a deal is almost done for the Bears in Arlington Heights. Why do we keep hearing about the Bears having a new stadium in Bridgeport? Presented by Ankin Law - Injury Law Made PersonalShop Sox Machine Merch: https://soxmachineshop.com/See omnystudio.com/listener for privacy information.

In Josh Nelson's upcoming Offseason Plan Project on Sox Machine, he technically shares seven players who are not returning, but four are grouped into two boats: backup catchers and inefficient (hurt) relievers. From this exercise, Josh and Jim Margalus agree that left field needs further discussion about how it plays out in 2027. Also, what to do about Andrew Benintendi? If he doesn't hit well early in the season, is he at risk of being waived? Use our code for 10% off your next SeatGeek order*: seatgeek.onelink.me/RrnK/TERRITORY10 Sponsored by SeatGeek. *Restrictions apply. Max $20 discount Visit the NEW Sox Machine Store at SoxMachineShop.com to pick up your new White Sox and Sox Machine Gear. Sam Antonacci, Munetaka Murakami, Tristan Peters, Chase Meidroth, and the celibate-for-Sean-Burke shirt! Plus new Sox Machine 3/4-zip quarter-zips, Sweaters, and Coffee Mugs. Presented by Ankin Law - Injury Law Made PersonalShop Sox Machine Merch: https://soxmachineshop.com/See omnystudio.com/listener for privacy information.

With the World Series beginning, it's time to launch Sox Machine's Offseason Plan Project (OPP). If you're new to the OPP, step into the role of Chicago White Sox GM. With a $130 million payroll budget, how would you build a 26-man roster to improve on the 84-78 record? This episode will guide you through the decisions you'll need to make before wheeling and dealing in free agency and trade markets. To get your new wireless plan for just 15 bucks a month, go to MintMobile.com/Territory. That’s it; there’s no catch.  Visit the NEW Sox Machine Store at https://SoxMachineShop.com to pick up your new White Sox and Sox Machine Gear. Presented by Ankin Law - Injury Law Made PersonalShop Sox Machine Merch: https://soxmachineshop.com/See omnystudio.com/listener for privacy information.

It's the annual quiz to name every player who appeared in a Chicago White Sox game in 2026. The total list includes 59 players who played at least one game. Link to play the quiz: https://soxmachine.com/2026/10/sporcle-saturday-your-2026-chicago-white-sox Plus, a World Series preview, and Josh Barfield is rumored to be running for the Houston Astros GM opening. Visit the NEW Sox Machine Store at SoxMachineShop.com to pick up your new White Sox and Sox Machine Gear. Presented by Ankin Law - Injury Law Made PersonalShop Sox Machine Merch: https://soxmachineshop.com/See omnystudio.com/listener for privacy information.

New podcast discussing in depth the Chicago White Sox three offseason dilemmas: What to do with Colson Montgomery? Should Sox sign a contract extension with Munetaka Murakami? What role does Luis Castillo have with the team in 2027? Plus, discussion about the ALCS, Cleveland's weird home vs. away splits, and how much World Series tickets are going for in Milwaukee. Use our code for 10% off your next SeatGeek order*: seatgeek.onelink.me/RrnK/TERRITORY10 Sponsored by SeatGeek. *Restrictions apply. Max $20 discount Presented by Ankin Law - Injury Law Made PersonalShop Sox Machine Merch: https://soxmachineshop.com/See omnystudio.com/listener for privacy information.