Some literary scholars, including Curnutt, agree that the character of Richard Gordon was created for Hemingway's close friend and author, John Dos Passos. Kenneth Lynn says, "Gordon is a vicious caricature of Dos Passos, and the question is what had the novelist done to incite it" (Lynn, quoted by Curnutt  124). Dos Passos was the first person to suggest that Hemingway move to Key West. Dos Passos even met his wife, Katherine "Katy" Smith through Hemingway, when Dos Passos was visiting him at his first apartment in key West. Dos Passos's wife, Smith, is also the inspiration behind the character of Mrs. Helen Gordon. However, their once seemingly strong friendship eventually led to a rivalry as Dos Passos's writing career blossomed in the 1930s, by the time To Have and Have Not was published. In stark contrast to Dos Passos's success was Hemingway's struggle, as he hit a low point in his own writing career, according to Curnutt, who, in agreement with other critics, states that their rivalry was created out of were jealousy on Hemingway's part (Curnutt 125). Pizer argues, "Dos Passos was merely a scapegoat for Hemingway's own self-recrimination" (Pizer, quoted by Curnutt 125). Hemingway's resentment towards Dos Passos would only intensify later in A Moveable Feast, as he would blame the end of his marriage to Hadley Richardson on Dos Passos. 

 

Due to the fact that Richard Gordon's character is often associated with John Dos Passos, it would not be out of the ordinary to consider Helen Gordon, wife of Richard Gordon, to be based on Katy Dos Passos, wife of John Dos Passos (as mentioned in the aforementioned annotation). Hemingway met his first wife, Hadley Richardson, through Katy Dos Passos. Hadley did think of Katy as a close friend, but was aware of Hemingway's strong attraction towards Katy. Furthermore, John and Katy Dos Passos wanted to have children, but Katy suffered multiple miscarriages, which was a major disappointment to the couple. On a similar note, in To Have and Have Not, Richard Gordon condemns Helen for not being able to bare children, and mentions an abortion. Curnutt writes, "Hemingway thus conflates the Dos Passoses' money and fertility problems to insist that Richard Gordon forced his wife to have an abortion" (Curnutt 127). On the other hand, Curnutt suggests that due to Helen Gordon’s religious nature, she could not have been modelled on Katy Dos Passos because Katy was agnostic. Therefore, Curnutt presents a counterargument that some critics have made—that Helen Gordon is based on Pauline Pfeiffer, Hemingway’s second wife. Similarly, literature student Jordan Huden argues that Helen Gordon is a representation of Pauline Pfeiffer because the fictional marriage between Richard and Helen mirrors the marriage and struggles recorded in Hemingway and Pfeiffer’s marriage, as both ended due to contrasting religious beliefs (Huden 5). Huden also makes a connection between the headboard placed above Hemingway and Pfeiffer’s bed and their struggles. Huden writes, "Though the situation presented in To Have and Have Not is not identical to the troubles in his own marriage with Pfeiffer, it highlights the role of religion as a divisive power when it comes to relationships, a sentiment that still reads relevant today. Overall, it can be argued that the sprawling wooden headboard hung over the bed that Hemingway and Pfeiffer once shared serves not only as aesthetically pleasing decor, but as a sort of twisted symbol of the way in which Catholicism may have affected their marriage. The headboard coming to be this symbol of their ruined marriage is ironic, as both instances of marriage, Hemingway and Pfeiffer’s and the fictional Richardsons, ended due to conflicting religious beliefs that involved acts that would happen in a bedroom" (Huden 5).