Willy Loman's twenty-thousand dollar proposition is his plan to commit suicide in order for his family to collect twenty-thousand dollars for his life insurance policy. Willy has gradually been losing his mind and cannot deal with the stress of not succeeding as a salesman. He has already been in several car accidents, and Linda even finds a rubber hose that Willy plans on using for another suicide attempt. After Willy gets fired, he comes home and begins planting seeds outside. While Willy is planting seeds, he hallucinates and carries on a conversation with his dead brother Ben. Willy elaborates on his twenty-thousand dollar proposition and describes how he envisions his funeral. Willy dreams that his funeral will be massive and thousands of people will come from all over the United States to attend his funeral. Willy hopes that the massive crowd will astonish Biff, who will be impressed and regret that he ever doubted his father's success.

As Willy's emotional disintegration continues, he begins to consider suicide. Linda's finding the piece of rubber hose in the basement is one sign, for sure. Willy's increasingly frequent car accidents may be another. By the conclusion of the play, Willy is moving closer to taking his own life, thinking that the proceeds from his insurance policy ($20,000) will do more for his family after he is dead than he can do for them while he lives. In his troubled state, he has another hallucination in which he talks to his brother Ben, long dead. He explains his $20,000 "proposition" and seeks Ben's thinking in the matter. As he carries on his conversation with Ben, we gain insight into Willy's feelings and sense of failure. He imagines his own funeral, with people coming from great distances to pay respects to him. He loves the idea that at his funeral his sons will realize what a "great man" he had been. He imagines what great things Biff can do with $20,000 to back him up. In the hallucination, despite raising the issue of cowardice, Ben finally agrees with him. Willy does take his own life. Few attend his funeral, and his grieving wife is left wondering why he would choose to leave her.