When I think about a rugged individualist the first thing that pops in my head is Odysseus from the Odyssey.
For those who don't know the Odysseys is basically about Odysseus’ journey to get back home after the Trojan war. However he faces many trials from Poseidon because Poseidon gets disappointed when Odysseus thinks that the Greeks didn't need help from the gods to win the war. He and his crew-mates face many trials and a lot of them lose their life before they can actually get back home. Well all of the crew.
Throughout his journey he's the one who manages to get his crew out of trouble. He came up with idea to hide under the sheep to escape the cyclops, he got his men to leave, and more. he's the brains of his crew, he knows a lot more than his other fellow crew-mates and he's favored by some of the gods.
Odysseus is a rugged individualist because he is more intellectual than other people. Even at the end when all his crew members are dead he is still determined to get back home and eventually does so. Even during the the Trojan War he came up with the genius plan to make a Trojan horse so they could penetrate through the Trojan defense. It's thanks to his genius plan the war ended sooner.