Winkler's career was spent in the transportation field, starting when he began working for the B&O Railroad in 1945, moving to the Chicago, Burlington & Quincy in 1953, occupying sales positions in the passenger department. In 1959 he moved into freight sales with the L&N Railroad, and advanced in freight sales to become Philadelphia general agent for the RF&P.
In 1968 he left the railroad industry and joined the traffic department of Westinghouse Electric Corp., Power Systems Division, Lester, Pa, where he later became traffic administrator, for 17 years until the plant closed in 1985.
Winkler returned to the railroad industry by joining the Eastern Shore Railroad (now Bay Coast Railroad) as sales manager, and in 1987 joined Bridgeton, N.J.-based Winchester & Western Railroad as general agent, where he spent the past 25 years.
Winkler also served on the Interstate Commerce Commission and was a longtime member of the South Jersey Transit Corp. Advisory Committee, a member of the National Railway Historical Society, member of the Traffic Club of Philadelphia, and a member of the New Jersey Association of Railroad Passengers.
A founding member of the New Jersey Shortline Railroad Association, Winkler was co-recipient of the 2004 Benjamin J. Friedland Award, given annually by the association for “Meritorious Service to the Railroad Industry.” Winkler’s guidance also contributed to the Winchester & Western being named 2002 Short Line of the Year by Railway Age.