Chicago Cubs (74-55): Jon Lester, P
In a talent-packed NL Central, the Cubs are set for a franchise season and will have to make the playoffs by way of the Wild Card. This means they will be handing the ball to Jon Lester for the play-in Wild Card game. Lester has certainly had a wish-washy season with a 3.59 ERA, but the Northsiders have no choice but to rely on their superstar ace in October.