Wolf began his aviation career in 1966 with American Airlines, where he advanced to the position of vice president of the Western Division.

[citation needed] In 1987, Wolf left Flying Tiger to lead Allegis Corporation, the former parent company of United Airlines.

[4] Wolf served on the boards of directors for R. R. Donnelley & Sons Company, Philip Morris International, and Chrysler Group, LLC.

[8] Wolf holds a bachelor's degree in sociology from San Francisco State University.

[11] Since 1990, Wolf has donated more than $19,000 to Republican causes, including supporting the political campaigns of John McCain, Thomas M. Davis, Sue Lowden, Lauch Faircloth, Linda Lingle, Josh Mandel, Lynn Morley Martin, Michael Castle, and John Warner.