Craig Counsell–Devin Williams reunion could be perfect fit

Under Counsell’s leadership, Williams delivered some of the finest seasons of his career, earning NL Rookie of the Year honors in 2020, two Trevor Hoffman Reliever of the Year awards, and a pair of All-Star selections. From 2019–2023, he posted three seasons with an ERA under 2.00 and another at 2.50, capped by a 36-save campaign in 2023.

Stress fractures in his back sidelined Williams for much of 2024, Counsell’s first year managing the Chicago Cubs. Before the 2025 season began, Williams was traded to the New York Yankees, where he endured the toughest campaign of his career, posting a 4.79 ERA and allowing more earned runs than he had in the previous three seasons combined.

Despite his struggles, MLB Trade Rumors ranks Williams as the second-best reliever on the market and the 16th-best free agent overall. His rough 2025 season may limit him to a shorter or less lucrative contract, creating a prime opportunity for the Cubs to pursue him on a deal featuring options and/or incentive-based bonuses.

If Chicago were to sign Williams and reunite him with Counsell, he could immediately step into ninth-inning duties. And if he recaptures his previous form, it could position him for the lucrative payday he’s aiming for in free agency, one far greater than what he’s likely to receive this offseason.

In the end, a Counsell–Williams reunion feels like a move that benefits everyone involved. Williams would return to the manager under whom he thrived, giving him the best chance to rebound and rebuild his value. Meanwhile, the Cubs desperately need to rebuild their bullpen that saw a vast majority of key contributors depart for free agency.