David Senra

July 26, 2021

Writer, Sailor, Soldier, Spy: Ernest Hemingway's Secret Adventures, 1935-1961

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My highlights from the book:

1. Hastily pulled together to fight the Axis, OSS was an odd creature—at once a collection of men and women from the upper crust of society on America's east coast, and a magnet for astonishingly talented and creative people from all walks of life, from Wall Street lawyers to Hollywood filmmakers, even the future chef Julia Child. In OSS they could almost literally design their own adventures.

2. Hemingway would not have been out of place in OSS. He loved secrets, and the edge they gave him. He craved action, but was not cut out for conventional soldiering. He moved easily between social and economic classes-and across borders.

3. The writer had tried his hand at various forms of spying and fighting on two continents. The way stations were varied, often exotic: the battlefields of Spain, the backstreets of Havana, a junk on the North River in China.

4. He seemed to gravitate to men and women who operated on their own in the shadows.

5. The characters he created embodied so many American values we still cherish: truth, bravery, independence, grace under pressure, standing up for the underdog.

6. His voice was uniquely American and revolutionary. He had changed the course of American literature in the 1920s.

7. His greatest work, after all, came from sharing, not hiding, his life experiences.

8. Hemingway was not there just to observe.

9. Hemingway had climbed to the top of his profession.

10. His two bestsellers, The Sun Also Rises and A Farewell to Arms, reflected how much he had lived in his first three decades: wounded veteran by nineteen, then foreign correspondent for the Toronto Daily Star and member of the Paris branch of the "Lost Generation" of legendarily talented writers.

11. His writing honestly and undauntedly reproduced the hard countenance of the age with a trademark combination of simplicity and precision. When he wrote, he was the soul of brevity, telling compelling stories in spare prose that spoke to millions of readers.

12. His central theme was personal courage: he displayed "a natural admiration for every individual who fights the good fight in a world overshadowed by violence and death."

13. Hemingway was so successful that he was now on his way to becoming a touchstone for every American writer, and a role model for not a few American individualists. They were reading Hemingway, quoting him, copying his behavior, and seeking his advice.

14. He had only a handful of competitors.

15. Hemingway placed a premium on rugged self-reliance.

16. For most of his life, Hemingway liked to live on the edge and take risks. But the expression on his face suggests that, at least this time, the brush with death was close enough for him.

17. He wanted to be the war writer of his generation; war gave answers that could not be found elsewhere.

18. They were filled with tough, colorful, and educated men (as well as a few women) from various countries, including the United States, the kind of people who appealed to Hemingway. They were not just scribblers or dreamers, but men risking their lives for their beliefs-they were authentic.

19. As he had tried to explain to the guerrillas, the writer and the reporter were different. The reporter wanted facts for a story to file as soon as he could get it through the censor; the writer wanted to absorb the experience of wartime.

20. Nor did Hemingway appreciate the lecture on the laws of war that followed, how reporters had no legal right to carry sidearms.

21. He was willing to make personal and professional sacrifices.

22. For Hemingway now was the time to withdraw from the world and work. "The only thing about a war, once it has started, is to win it—and that is what we did not do.  I am not killed so I have to work. The hell with war for a while."

23. Ernest had a better grasp of the law of the jungle than of politics. He was more like a hunter than a politician; he thought in terms of black and white, of life or death.

24. Hemingway did not stand for Western democracy but for experiencing life in all its fullness in places like the hills of Africa or the waters off Key West.

25. Hemingway remained deeply absorbed in his book about the Spanish war, occasionally surfacing to write letters or tend to Gellhorn. She commented in a letter that he was "like an animal" with his manuscript, keeping it close to him or hiding it in a drawer under other papers. He never willingly showed it to anyone, and would not talk about it.

26. In his mind he was more than just a novelist or a journalist: he was a sophisticate who understood how the world worked, and could use his understanding to help shape events.

27. Hemingway thought that spying was one more of his many life skills, and he was not wrong.

28. Another trait he shared with other spies was an assumption that everyday rules did not apply to him. Hemingway had been living by his own code for decades. In literature it had to do with his revolutionary writing style.

29. He described how it felt "almost too good" to write as well as  he could, and then to have his work sell.

30. His preference was for loose affiliation with other irregulars, especially guerrillas, which made him feel like he was a part of the action but left him free to come and go as he pleased.

31. Hemingway was a man who did not mind hardship, especially in the service of a cause he believed in, but he also handily tolerated luxury.

32. During the previous four years he had immersed himself in a series of life events that would have exhausted most mortals: infidelity, divorce, and remarriage; committing himself heart and soul to a lost cause in Spain; cutting his ties to Key West and moving to Cuba; writing a 470-page masterwork of world literature; and traveling to another war in an unknown part of the world.

33. Most rooms would soon turn into branches of the main library in Hemingway's study. Stacks of books sprouted on almost every available surface; by 1961 there would be something like 7,500 books in the house.

34. Life in Cuba was more colorful and exciting than life at home. The rules were different-that is, when there were any rules at all.

35. The submarine slipped from sight, and Pilar floated alone on the ocean. The event was a disappointment for Hemingway the warrior, ready to die for his country; he and his crew would, he wrote later, have all gone to "Valhalla" for eternity, "happy as goats.”

36. He called in favors to get himself as close to the invasion beaches as possible. From a landing craft, he watched history unfolding in the waters off Normandy on June 6, 1944. Around and behind him was one of the greatest armadas in history.

37. Bruce charged Hemingway with keeping order at the Grand Veneur, and he did it in his own way. He is said to have come up with the novel idea of making his German prisoners take their pants off (on the theory that a man without pants was less likely to escape).

38. When I dream of the afterlife the action always takes place in the Paris Ritz, Hemingway once wrote.

39. Hemingway had displayed that rare combination of advised recklessness and caution that knows how properly to seize a favorable opportunity which, once lost, is gone forever.

40. He is a born leader of men, and, in spite of his strong independence of character, a highly disciplined individual.

41. The allegations were that he had stockpiled weapons, commanded troops, and joined the fight to liberate Paris. These allegations were all true.

42. For the writer-soldier, war was the ultimate life experience. "It is wicked to say but that is the thing I love best."He felt most alive when risking his life, all of his senses fully engaged.

43. Hemingway begins by questioning McCarthy's courage and war record. He tells McCarthy that he is "a shit" and invites him to come to Cuba for a private boxing match to settle their differences.

44. The Old Man and the Sea is a novella about a poor Cuban fisherman named Santiago who is engaged in a personal struggle for survival.

45. As Santiago/Hemingway famously tells the reader, "A man can be destroyed but not defeated." Santiago fought the good fight and endured with style and grace. He triumphed in spirit.

46. The writer should always strive to create “something that has never been done or that others have tried and failed."

47. He didn't even have the will to read, a touchstone in his life that he had "loved above everything." Writing was even more difficult.

48. At the airport he attempted to walk into a whirling airplane propeller.

49. He had gotten up before anyone else, padded quietly downstairs, and, with one of his doublebarreled shotguns, killed what was left of the great American writer who had fought so hard for what he believed in.

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About David Senra

Learn from history's greatest founders. Every week I read a biography of an entrepreneur and tell you what I learned on Founders podcast