Jake Barnes was injured during WWI, and his injury is not a broken bone or amputation, it's one that not only hurts him physically but mentally. Jake's manlihood was injured during the war, and he can no longer use sex to assert his masculinity. He turns to other methods such as alcohol, financial stability, travel, and even violence and bashing of other characters to show how much of a man he is.
Jake has a lot of money. Despite
his serving in the war, he is still very well off and is able to live a
first class lifestyle. The fact that he is wealthy doesn't really help
him be more masculine, but what he does with his money does.
Jake uses drinking throughout the novel to assert his manliness. Because of his castrating war wound, Jake must make up for his loss by proving himself in different ways. In Pamplona, Jake is taught to drink from the goatskin bags. He drinks excessively from these bags in front of the locals, showing that he is worthy and socially acceptable. A more general use of drinking, which is used heavily in The Sun Also Rises, is the use of alcohol in order to assert friendships. Jake sometimes buys everyone he's with drinks in order to take care of both of these, he asserts that these people are his friends, and also shows that he has enough money to buy drinks for everyone, which is masculine.
Another way Jake uses his money to assert his masculinity is to travel to many different places with and without friends. He travels with Bill to Pamplona and to the fiesta with Bill, Mike, Cohn, and Brett. He also travels within Paris a lot. When he travels, Jake is seemingly carefree with his money. Take, for example, the fiesta and bullfighting. Jake and Bill get seats really close to the action, which must've cost more than the balcony seats. Jake doesn't even mention this in the book which shows he must have more than enough money to afford them and seats like these are commonplace for him.
Some prominent examples of Jake asserting his manliness come at the very beginning of the book, when he talks about Cohn. Jake mentions that Cohn has one a boxing title, but says that it is good for Cohn, and talks about his boxing as if its sort of a cute little hobby for him. However, this cute little hobby of Cohn's ends up getting back at Jake at the fiesta.
At the fiesta, Jake (try's) using violence for the first time in the novel to show himself and Cohn that he has masculinity. Jake attempts to punch Cohn, but Cohn replies with a vicious attack that leaves Jake bloodied and embarrassed.
Jake is especially concerned about his masculinity in this book because of the constant pressure to please Brett. If he doesn't, he knows Brett will leave him. Over the course of the novel, we are introduced to two others who have feelings for Brett (Cohn and fiance Mike), as well as her soon-to-be ex-husband, Sir Ashley. Added to the pressure from these men is the fact that he is at an obvious disadvantage because of his injury. At the end of the novel Jake realizes he and Brett won't end up together, which is sad but may lift some of the weight on Jake's shoulders, because he won't have to try as hard to prove himself.
I don't know that we can call Jake "wealthy." He's the only one among the gang, it seems, with an honest job, and he makes a point of telling us that he's up early going to work while Brett's sleeping past noon. And he's a correspondent for an American newspaper, posting stories on stuff he's not apparently all that interested in. He makes a living, he can pay his way (unlike Brett, who has to depend on the generosity of strangers and friends), and these are a source of pride for him, but it's more of a working-class ethic of doing a job for honest pay. Maybe there's a masculinity thing here, too: the others seem decadent, whereas Jake works for his money, and when he goes back to his room he balances his checkbook responsibly. Like a grownup.
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