After overhearing his colleagues talking about bets they've won or lost, Matthew is eager to become a gambler, too. But when he asks for help, Matthew's irritating persistence prompts Joe to teach him a lesson he'll never forget. Meanwhile, when Jimmy can't make it to a big broadcasters dinner, he gives his seat to Dave. And Dave accepts before learning that he'll be expected to introduce the evening's keynote speaker, Bill. Recalling his own dismal record at speechmaking, Dave nervously sits down to compose his remarks. And while Bill offers him some pointers, the helpful hints only serve to make him angry as well as nervous. In order to help Dave out, Beth makes preparations for him to try out his speech. Only his confidence isn't boosted by the distractions offered by her and Catherine. Meanwhile, after losing bet after bet, Matthew suddenly finds himself owing Joe thousands of dollars. After learning of Matthew's mounting debt, Lisa tries getting to Joe to call the whole thing off. But the losing streak continues despite a chance to win everything back. Fearing that Dave's introduction will fall flat, Bill tries one more time to coach him. But an angry outburst ruins Bill's voice, leaving him unable to speak at the dinner. Finally, after realizing that Matthew has been duped, Jimmy wins back the hapless reporter's money.