After a 21-year career at WGN Radio, Kaplan signed a multi-year deal with ESPN in 2015 and he started as the host of "Kap and Co.", a daily sports radio show that aired on ESPN 1000 in Chicago from 9:00 AM CT till Noon. His co-hosts included US Hockey Hall of Famer Eddie Olczyk who is also the color analyst of the Chicago Blackhawks TV broadcasts and the NHL on NBC in addition to his horse racing analysis on NBC Sports and NBC Sports Chicago broadcaster Pat Boyle. Currently, Kaplan co-hosts "Kap and J. Hood" with Jonathon Hood on ESPN 1000 from 7:00 to 10:00 AM CT. Throughout his tenure on the "Kap and J. Hood" show, Kaplan has been both praised and scrutinized for his "Hot takes" and "Dramatic Flips". His charisma paired with J. Hood, has successfully garnered productive and entertaining conversation on Chicago's sports teams every morning.