On July 2, 2013, Strop was traded along with Jake Arrieta from the Orioles to the Cubs in exchange for Scott Feldman and Steve Clevenger. In 2016, Strop made 54 appearances with a 2-2 record and a 2.85 ERA. The Cubs would eventually win the 2016 World Series, giving Strop his first world series title.
This Rawlings official MLB baseball was signed in blue ballpoint pen by Strop and includes a Great Moments COA.