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Among his holdings were a number of railroads, including the Omaha and Northwestern Railroad, the Denver and South Park Railroad, the Sabine and East Texas Railway, the Boston, Hoosac Tunnel and Western Railway, and the Troy and Boston Railroad.
Working first as foreman of a crew hired to supply railroad ties, and then as manager of a large railroad construction gang, Paxton contracted with the Omaha and Northwestern Railroad in 1869 to build lines north out of Omaha to Oakland, Nebraska.