Mr. Burns sits in his office awaiting the union leader, who mysteriously disappeared after promising to clean up the union, so that they can discuss the proposed union contract. While perusing the contract, Burns becomes disgusted with the union demands and reminisces about simpler times in which disgruntled workers were simply walled up in coke ovens. Burns then decides to take on the union, and revokes their dental plan.
Meanwhile, at Painless Dentistry, the Simpson children are getting their teeth checked. It is discovered Lisa needs braces. When Marge informs Homer, he tells her not to worry about the cost, as the union had won a dental plan during a previous strike. Later, at a meeting of the local chapter of International Brotherhood of Jazz Dancers, Pastry Chefs and Nuclear Technicians, Carl announces that the newest contract requires the union to give up their dental plan in exchange for a free keg of beer for their meeting. Homer slowly comprehends that giving up their dental plan would require him to pay for Lisa's braces and jumps into action, reminding everyone how their dental plan has helped them all.
Carl proposes Homer be the new union president and he is promptly elected by a nearly unanimous vote. Mr. Burns watches Homer on his hidden camera, and is intimidated by his energy. Burns invites Homer to his office with the intent of bribing him, but Homer misconstrues Burns's sly innuendos as sexual advances. Homer quickly gets to his feet, saying he does not go for those "back door shenanigans" and promptly leaves, a series of events which establishes the idea in Burns's mind that Homer is honest and incorruptible.
Mr. Burns sends hired goons to the Simpson house in order to take Homer back to Burns' Manor to negotiate. While Burns is setting the agenda for the discussion, Homer is struck by the urgent need to use the rest room. Homer asks Burns where the rest room is and immediately leaves, leading Burns to conclude that Homer is a tough negotiator who is unwilling to even hear him out. At a later union meeting, Homer tries to resign, tired of meeting with Mr. Burns. The union misunderstands his frustration, and the members nearly unanimously decide to strike. Mr. Burns is undeterred by the strike and tries several methods of breaking it up, but fails. On an edition of Kent Brockman's talk show Smartline, Burns is allowed an opening tirade and he threatens dire events if the strike is not concluded.
Later, Burns and Smithers march to a secret room in the Power Plant and turn off the power for the entire town. The strikers do not lose hope and begin to sing. Burns, confident he has broken the union's spirit, steps out on his balcony to hear their reaction but is disarmed by their unity and optimism. Burns finally calls a meeting with Homer to concede to their demands on one condition: that Homer resign as union president. Homer celebrates madly, leading Burns to finally realize that Homer is not the "brilliant tactician" he thought he was. With the Simpson family insured again, Lisa gets her perfect new braces and she, the Simpson family, and the dentist gather and laugh as the episode comes to a close.