Don't Meet Your Heroes, Especially the Dead Ones

In 1933, Hemingway needed money. Esquire needed a writer. A boat brought them together. It's a mostly true story that speaks volumes about the lives of men then and now.

- By David Coggins

Ernest Hemingway aboard his fishing boat, Pilar, which he bought with the help of this magazine.

WHEN ERNEST HEMINGWAY WASN'T AT FINCA VIGÍA, HIS HOUSE 30 MINUTES FROM HAVANA, he was likely at the Floridita, drinking frozen daiquiris at the end of the bar. Hemingway was very specific about those daiquiris, as he was with many things. They contained two shots of rum but no sugar-his daiquiri record in a single night was 16. Remember, they were doubles, but who's keeping track? These days, the Floridita is a tourist theme park with a life-size Hemingway statue installed along the rail. A statue in a bar means its best days are behind it. One look inside and you know to keep walking. The old magic is long gone.

Hemingway was a regular at the Floridita, but he spent even more time on the water, aboard his beloved Pilar, the boat he owned nearly half his life. This was where he fished, of course, and where he entertained his children and wives number two, three, and four, as well as legendary anglers, film stars, publishers, suitors, sycophants, and soon-to-be enemies. How Hemingway acquired Pilar is tied up in the history of this magazine, and where the boat rests reveals the complicated legacy of its owner, who, along with Esquire, helped define how men lived in the 20th century. In a life of celebrated stories, many exaggerated, this story has the benefit of being true. Or true enough, anyway.