Chicago Cubs: Top five moments during the team’s window of contention

Chicago Cubs: Which signing was more important?

While one was more a hiring than a “signing” per se, both guys had to sign on the dotted line regarding their intentions to join the Chicago Cubs. Many have said that the Jon Lester free agent signing is the best in Chicago sports history, yet one just as important preceded his signing by 38 days. When the Cubs fired poor Ricky Renteria and announced the hiring of the idiosyncratic Joe Maddon, the gauntlet was thrown down to the rest of baseball: the Cubs aren’t just lovable losers anymore: we are for real.

Think what you will of Maddon and the end of his tenure with the ball club, it is undeniable that his unique managerial style enabled the Cubs to win a World Series. He communicated with his players, he was charismatic with the Chicago sports horde, and his lax managerial style allowed many of his young players to flourish. Then again, this was only possible, in part, because of the signing of Lester on December 10, 2014.

Lester brought an ace mentality to the team and his signing signaled a new era in Cubs history. Theo Epstein’s decision to pay the big lefty big money was just the sign many in Chicagoland and beyond needed to take this team for real. It also paved the way for a guy like David Ross to join the flock, a move that’s still paying dividends for the organization.

It wasn’t so much his performance that was important to the Cubs, although Lester did compile a 77-44 record and 3.64 ERA over six seasons with the club. It was the grit he brought, the aura he emanated, and the leadership he personified. This Lester and Maddon debate is sorta like the chicken or the egg discussion: at this point it’s a moot point because we needed them both.