Kirk examines what could have been if Jared Carrabis's life took a more corporate path through the ranks of Major League Baseball front offices. Meantime, Jared is addicted to his new watch. As the team prepares for trivia Monday night, more controversy behind the scenes with a certain Barstool Sports employee. Intern Justin offers his best prep trivia prep session (0:25:30). Kirk has decided that Woody Allen got a raw deal (0:53:30). For the first time, Kirk offers details about The Case, the cold case podcast he's developing for Barstool Sports.