David Kaplan Talks Cubs Book, Hawks Vs. Bulls, and Ill-Fated Shawn Kemp for Scottie Pippen Trade Sco

Ryan Glasspiegel

David Kaplan, who hosts Kap + Co. on ESPN Chicago and Cubs pre and postgame as well as SportsTalk Live for CSN Chicago, joins the podcast. Kaplan recently published a book entitled The Plan, a behind the scenes look at how the Ricketts family bought the Cubs, hired Theo Epstein and Joe Maddon, and assembled what they hope will be a dynasty. We discussed:

  • Did Kaplan really have the premonition to start writing this book before the Cubs even won the World Series?
  • The anecdote from the book that when the Ricketts family bought the team season tickets were still exclusively renewed by fax machines, and how that was a metaphor for the state of the organization’s disrepair.
  • The process of retaining a sports banker before the Cubs even came to market.
  • Do the Cubs win Game 7 without the rain delay?
  • Have the Blackhawks become more relevant than the Bulls on the north side and in the northern suburbs of Chicago?
  • Getting fired by the Cubs as a beer vendor in the 80’s.
  • How his scoop of a Shawn Kemp for Scottie Pippen trade before the lead-up of the 1994 Draft led to the swap getting canceled because Sonics fans revolted and the team pulled out of the deal.

As we discussed, when I first moved to Chicago I thought Kaplan’s sports talk radio persona was over-the-top, but having lived here for eight years now I’ve come to appreciate his authenticity. Hope you enjoy the conversation!