The Cubs and Cardinals are currently in the midst of an intense playoff series, but both clubs could undergo some significant roster change this winter. According to a report from Nick Cafardo of the Boston Globe, the Cubs are "not out of the realm of possibility" for Cardinals right-hander John Lackey, who will become a free agent this winter.
Lackey, 36, is expected to consider the Cubs due to his familiarity with Theo Epstein (who signed Lackey in Boston) and close friendship with former teammate Jon Lester. Chicago is expected to be in the market for starting pitching behind Lester, Jake Arrieta and Jason Hammel. The club also has Kyle Hendricks and some prospects as options for the rotation but is considered likely to add a starter to replace Dan Haren, who is retiring.
Lackey is expected to draw significant interest on the free-agent market after posting an excellent 2.77 ERA in 33 starts for St. Louis this season. The Cardinals will probably have try to retain the veteran after having him as an effective part of their staff for the last year and a half, and the Astros and Rangers may be considered options due to Lackey's ties to the state of Texas.