Westerberg was arrested for selling illegal signal descramblers for satellite TV. These boxes made it possible for people to watch satellite television without paying for a subscription. Westerberg was caught and sentenced to prison for four months.
Westerberg lived in Carthage, South Dakota and earned a living as a traveling grain harvester. He and his crew would travel the plains, harvesting wheat and barley. Westerberg met McCandless when he picked him up hitchhiking outside of Cut Bank, Montana. Westerberg and McCandless hit it off, and McCandless worked at a grain elevator Westerberg owned for a time. When Westerberg was convicted, the work at the elevator dried up, and McCandless moved on.
McCandless's link with Westerberg proved to be durable, however. McCandless was always finding surrogate families during his travels, and it's clear he considered Westerberg's Carthage home, where he lived with several of his crew members, a kind of refuge. Carthage itself was a small, out of the way place, and its obscurity suited McCandless well. Westerberg remembered McCandless as outgoing, smart, and hardworking—almost to a fault. Like other outdoor adventurers Krakauer mentions (Ed Abbey, Everett Reuss), McCandless had a need for human companionship that often was hard for him to square with his love of the wilderness. This partly explains why McCandless often would send post cards to Westerberg and used Westerberg's Carthage address as a home address.