Jon Lester became the most important signing in Cubs history when he agreed to a six-year, $155 million contract to be the ace of the Cubs.
He spurned his old team — the Red Sox — along with a handful of other teams ready to pony up the nine-figure deal necessary to acquire the frontline starter. By choosing the Cubs, Lester accelerated Theo Epstein & Jed Hoyer's famous "Plan," legitimizing Chicago as a free agent destination and as an up-and-coming perennial playoff team.
"This signing really marks a transition of sorts for the Cubs, the start of a period where we are clearly very serious about bringing a World Series to the Cubs and the people of Chicago," Epstein said back on Dec.