Jon Lester was one of the biggest free agent signings in Chicago sports history and his contract is up at the end of the season, which could mean he may have pitched his final game at Wrigley Field. David Kaplan and Gordon Wittenmyer discuss and debate Lester’s Cubs career and if he is the most impactful Cub ever. Later on in the pod, the guys discuss a tough offseason ahead for the Cubs and if they should continue forward with their core or prepare for a rebuild.

(1:45) - Is Jon Lester the most impactful Cub of all-time?

(9:25) - Will Lester make the Hall of Fame?

(15:00) - Tough offseason ahead for the Cubs

(22:25) - Has Kris Bryant’s Cubs career been disappointing?