Many teams look for young talent under control for several years and work to make a trade to get those guys in the system. The Chicago Cubs were always on the lookout for those types of arms. Kyle Hendricks was one of those. But in 2015, the Cubs decided to go ‘all-in’ during free agency, signing Jon Lester to a six-year deal worth $155 million, plus a team option for 2021. Lester was 31 years old, although well established as a ‘big game’ pitcher.’ But while the Cubs were close, this seemed a bit much.
Chicago Cubs: Jon Lester defying Father Time at 35
