For the first time in a year, David and Jack conduct an Underemployed episode via Skype, catching up on Jack's new job, from the initial struggles to the eventual triumphs. They also talk about the Nats World Series run (recorded when they were up 2-0), the comical nature of Dan Snyder's Redskins ownership, being one week away from Jack's sister's wedding, the entitlement of Bryce Harper's booing and hilarity of Kawhi Leonard's, and Jack bestowing the gift of Cowboy upon David!