| Year | Winner | Location |
|---|---|---|
| 1957 |
William J. Klein The Mason & Dixon Lines, Inc. Pennsylvania |
Chicago, IL |
| 1958 |
Robert E. Rudesill Glendenning Motorways, Inc. St. Paul, MN |
Miami Beach, FL |
| 1959 |
Jesse E. Albright City Express, Inc. Maryland |
Louisville, KY |
| 1960 |
Jesse E. Albright City Express, Inc. Maryland |
St. Paul, MN |
| 1961 |
William J. Klein The Mason & Dixon Lines, Inc. Philadelphia, PA |
Detroit, MI |
| 1962 |
Peter G. Granello The Mason & Dixon Lines, Inc. New York City, NY |
Dallas, TX |
| 1963 |
Paul D. Goode Suburban Motor Freight, Inc. Columbus, OH |
Miami Beach, FL |
| 1964 |
Irvin J. Frey Branch Motor Express Company Reading, PA |
Louisville, KY |
| 1965 |
Bonnie A. Robison Southwestern Transportation Co. Memphis, TN |
Kansas City, MO |
| 1966 |
Peter G. Granello The Mason & Dixon Lines, Inc. New York City, NY |
Minneapolis, MN |
| 1967 |
Malcolm E. Thompson St. Johnsbury Trucking Co. Springfield, MA |
Tulsa, OK |
| 1968 |
Daniel Darnold Cook Motor Lines West Virginia |
Cincinnati, OH |
| 1969 |
George P. Holick Eazor Express Illinois |
Denver, CO |
| 1970 |
Peter G. Granello The Mason & Dixon Lines, Inc. New York City, NY |
Miami Beach, FL |
| 1971 |
William J. Long Lyons Transportation Lines Ohio |
Houston, TX |
| 1972 |
Earl H. Hudson Johnson Motor Lines, Inc. North Carolina |
Louisville, KY |
| 1973 |
Robert H. Gardener Pacific Intermountain Express Indiana |
Denver, CO |
| 1974 |
Daniel W. Darnold Cook Motor Lines West Virginia |
Minneapolis, MN |
| 1975 |
Robert D. Suck Cook Motor Lines, Inc. West Virginia |
Indianapolis, IN |
| 1976 |
Montie T. Webster Lee Way Motor Freight, Inc. Oklahoma |
Fort Worth, TX |
| 1977 |
David R. Gressley Consolidated Freightways Ohio |
Kansas City, MO |
| 1978 |
Gary L. Tunsky, Sr. Briggs Transportation Company Minnesota |
St. Louis, MO |
| 1979 |
Bruce Lekson Midwest Motor Express Minnesota |
Phoenix, AZ |
| 1980 |
Irvin F Eberly A-P-A Transport Lancaster, PA |
Kansas City, MO |
| 1981 |
Elwood Sherer Yellow Freight System Manheim, PA |
Indianapolis, IN |
| 1982 |
Elwood Sherer Yellow Freight System Manheim, PA |
Kansas City, MO |
| 1983 |
Leo A. Plumley American and Produce Co. Eagan, MN |
Fort Worth, TX |
| 1984 |
Richard A. Gillespie Century Motor Freight, Inc. Minnesota |
Indianapolis, IN |
| 1985 |
Robert E. Friend Advance United Expressways Anthony, MN |
St. Louis, MO |
| 1986 |
Jay H Mammau Yellow Freight System Pennsylvania |
Kansas City, MO |
| 1987 |
Dwight Adkins C W Transport, Inc. Charlotte, NC |
Fort Worth, TX |
| 1988 |
Craig A. Green Consolidated Freightways Idaho |
St. Louis, MO |
| 1989 |
Doyle L. Martin Safeway Stores, Inc. Alexandria, VA |
Memphis, TN |
| 1990 |
Chet Radwan Yellow Freight Systems Illinois |
Dallas, TX |
| 1991 |
Mr. J. Craig Bonds P. F. S. Colorado |
Minneapolis, MN |
| 1992 |
Raymond Simon Yellow Freight System, Inc. Minnesota |
Nashville, TN |
| 1993 |
Dana E. Moore Boeing Licensed Transp. Washington |
Denver, CO |
| 1994 |
Horace A Davis, Sr. Union Pacific Motor Freight Texas |
Tampa, FL |
| 1995 |
Edwin Jarzenski, Jr. ABF Freight System Ohio |
New Orleans, LA |
| 1996 |
Warren M. Simpson Family Dollar Trucking North Carolina |
Columbus, OH |
| 1997 |
Raymond Simon Yellow Freight System, Inc. Minnesota |
Minneapolis, MN |
| 1998 |
Everett S. Macmaster Jr. Federal Express Corporation Maine |
Long Beach, CA |
| 1999 |
Kenny D. Wulf Farmland Industries, Inc. Iowa |
Tampa, FL |
| 2000 |
Mark Dewain Ritter Wal-Mart Stores, Inc. South Carolina |
New Orleans, LA |
| 2001 |
Raymond Simon Yellow Freight System, Inc. Minnesota |
Minneapolis, MN |
| 2002 |
Larry Brenn Wal-Mart Transportation, LLC Florida |
Milwaukee, WI |
| 2003 |
Dale L. Duncan Con-Way Western Express Arizona |
Columbus, OH |
| 2004 |
Edward F. Romero Con-Way Western Express Arizona |
Salt Lake City, UT |
| 2005 |
Rick Hebert Yellow Transportation, Inc. Illinois |
Tampa, FL |
| 2006 |
Mark Hassemer Yellow Transportation, Inc. Wisconsin |
New Orleans, LA |
| 2007 |
Alphonso Lewis Roadway Alabama |
Minneapolis, MN |
| 2008 |
Ryan R. Kelley FedEx Freight Iowa |
Houston, TX |
| 2009 |
Michael W. Stickley Con-Way Freight Virginia |
Pittsburgh, PA |
| 2010 |
Jason D. Matte FedEx Freight Mississippi |
Columbus, OH |
| 2011 |
Gary W. Harms Walmart Transportation, LLC Kansas |
Orlando, FL |
| 2012 |
Scott A. Stroup YRC Freight Nebraska |
Minneapolis, MN |
| 2013 |
Ralph B. Garcia ABF Freight System, Inc. New Mexico |
Salt Lake City, UT |
| 2014 |
James Quarles Walmart Transportation, LLC South Carolina |
Pittsburgh, PA |
| 2015 |
Bradley Lester FedEx Freight Oregon |
St. Louis, MO |
| 2016 |
Ronald Metternick FedEx Freight Michigan |
Indianapolis, IN |
| 2017 |
James Duffy FedEx Freight Wisconsin |
Orlando, FL |
| 2018 |
Nick Arnold FedEx Freight Oklahoma |
Columbus, OH |
| 2019 |
Adam Heim FedEx Freight Idaho |
Pittsburgh, PA |
| 2022 |
Martin McMahon RIST Transport New York |
Indianapolis, IN |
| 2023 |
Martin McMahon RIST Transport New York |
Columbus, OH |
| 2024 |
Joseph Hicks XPO Rhode Island |
Indianapolis, IN |