Kaplan hosted the pre game and post game shows for the Chicago Cubs on either radio (WGN Radio) or TV for 25 seasons from 1995 to 2019. He was the former pre and postgame host for NBC Sports Chicago's Chicago Cubs broadcasts where he partnered with former Chicago Cubs outfielder Todd Hollandsworth, former Chicago Cubs outfielder David DeJesus and former Cubs outfielder Doug Glanville. He also calls college basketball games for various conferences including the Atlantic 10 Conference on NBCSN, the Missouri Valley Conference, the Horizon League and several others. He has also been the announcer for the Chicago Machine and Chicago Shamrox.