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Wayne Westerberg offers Chris McCandless a place that he later regards as home, and he proves to be a close friend who never pressures McCandless to reveal more than he wants. McCandless first hitches a ride with Westerberg and intends to keep moving along, but Westerberg offers him a job and a place to live, so McCandless returns to Carthage. Westerberg’s welcoming house proves to be a sanctuary for McCandless. After living in Carthage, McCandless starts telling people he’s from South Dakota when asked. McCandless returns to work for Westerberg on several occasions over the course of his time roaming the United States. Westerberg remembers McCandless as a hard and uncomplaining worker. McCandless did the jobs no one else wanted to because they were tedious or dirty. Throughout his travels, McCandless keeps in touch with Westerberg, and he intends to come back and work for Westerberg again after his “great Alaskan odyssey.” Westerberg believes McCandless meant to keep that promise, and he struggles with the fall harvest in 1992 because he counted on McCandless’s help.

Westerberg first hires McCandless to work on a grain elevator, but McCandless is also a “farmer, welder, businessman, machinist, ace mechanic, commodities speculator, licensed airplane pilot, computer programmer, electronics troubleshooter, [and] video-game repairman,” according to Krakauer. In 1990, Westerberg is arrested for building and selling devices which allowed people to watch satellite television without paying for it. His arrest and subsequent time serving a sentence in Sioux Falls leaves McCandless without an employer and so prompts him to move on. McCandless writes to Westerberg in jail, and he continues to correspond with him until his final postcard before entering the Alaskan wilderness. 

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