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Jack Ferguson first came to Alaska during World War II when he was in the US Navy on the crew of a gasoline tanker delivering fuel in the Aleutian Islands. After the war, he went to Anchorage and immediately began work for the Alaska Railroad. He held a variety of jobs, including as a section crew member in Healy replacing ties and aligning track, a car oiler, a fireman in the engine on the Seward to Portage route, and an engineer based out of Fairbanks.