As things stand at this very moment, Jon Lester represents the best free agent signing in Chicago Cubs history. Not only that, but he’s in the conversation as one of the best free agent signings in Chicago sports history.
He’s toed the rubber 159 times in the regular season and another dozen times in the postseason for the club. His gutsy relief performance in Game 7 of the 2016 Fall Classic is etched into Cubs lore, as is his lasting legacy as the ace of the Cubs during the most impressive stretch in the modern era.