| 2019 | Daniel McCabe | Tacoma Rail |
| 2018 | Jake Nyman | Olive Group, LLC |
| 2017 | Ken Baune | Dependable Hawaiian Express |
| 2016 | Bryan Lovely | Toyota Lift Northwest |
| 2015 | Vince Santiago | VETrans LLC |
| 2014 | Tim Flood | Tacoma Rail |
| 2013 | Janice Wasson | Gordon Trucking |
| 2012 | Mark Miller | Ports America |
| 2011 | Lori Kincannon | McKinney Trailer |
| 2010 | Patricia Hutchinson | Pacer Transport |
| 2008/9 | Jeff Clark | Schneider National, Inc. |
| 2008 | Anita Lydiard | SCS Refrigerated Services |
| 2007 | Steve Fullerton | "K" Line America |
| 2006 | Kim Patera | Weyerhaeuser Company |
| 2005 | Gary Gieser | MacMillan Piper |
| 2004 | Sherry Yantzer | Honolulu Freight |
| 2003 | Mike James | Schneider National |
| 2002 | Rick Bunn | TOTE |
| 2000/1 | Mike Porter | American Fast Freight |
| 2000 | Ross Cook | Gordon Trucking |
| 1999 | Mark MacLeod | Best Ways Transportation Group |
| 1998 | Dave Castimore | Dave C. Castimore & Associates |
| 1997 | Ross Cook | Gordon Trucking |
| 1996 | Jim Stanaway | Excel |
| 1995 | Colleen Hubbard Pettibone | Omni Freight Services |
| 1994 | Steve Stone | Transport Logistics Inc. |
| 1992/3 | Rick Bunn | TOTE |
| 1992 | Lisa Zeiner | |
| 1991 | Bill Kaufmann | Bill Larson & Associates |
| 1990 | Patti King | Port of Tacoma |
| 1989 | Gary Roadhouse | C & H Transportation |
| 1988 | Orville H. Mooney | City Delivery |
| 1987 | Rick Bunn | TOTE |
| 1986 | Dennis Dean | Tacoma Rail |
| 1985 | Don Wallace | BN Inc. |
| 1984 | Wayne Flood | Roman Meal Milling Co. |
| 1983 | Curt Erickson | Erdahl Bros. Trucking |
| 1982 | Sherrill Goodman | IML Freight |
| 1981 | Durant Hehr | St. Regis Paper Co. |
| 1980 | | |
| 1979 | Richard A. Groves | Western Pacific RR Co. |
| 1978 | Lou Massotti | Buffelen Woodworking |
| 1977 | Jerry Casey | Transport International Pool |
| 1976 | Cliff Ellenwood | Ellenwood & Associates |
| 1975 | Bill Prather | The Milwaukee Road |
| 1974 | Fred Shinkle | St. Regis Paper Company |
| 1973 | Ed Davis | ONC Freight |
| 1972 | Don Luckey | BN Inc. |
| 1971 | C. Duane Kraft | Hooker Chemical Corp. |
| 1970 | Al P. Masek | Bekins Moving & Storage |
| 1969 | F.G. Rothwell | Union Pacific Railroad |
| 1968 | A.H. Dahl | St. Regis Paper Company |
| 1967 | William C. Dyer | Pacific Storage Inc. |
| 1966 | E.W. Jacobson | The Milwaukee Road |
| 1965 | E.W. Hilton | Simpson Timber Co. |
| 1964 | | |
| 1963 | Eugene Otis | WUTC |
| 1962 | | |
| 1961 | | |
| 1960 | | |
| 1959 | | |
| 1958 | William "Bill" V. Rutherford | St. Regis Paper Company |
| 1957 | Larry McCubbin | Burlington Northern RR |
| 1956 | Dick Thomas | Consolidated Freightways |
| 1955 | Ray Quinlivan | Carling Brewing Co. |
| 1954 | Don Pravitz | Great Northern RR |
| 1953 | Ted Hamilton | Nalley's Fine Foods |
| 1952 | Les Gorey | Pacific Highway Transport |
| 1951 | John Dyer | Pacific Storage, Inc. |
| 1950 | Art Reder | St Regis Paper Company |
| 1949 | Emmett Maloney | The Milwaukee Road |
| 1948 | Mort Woodward | Baker Dock Company |
| 1947 | Rufus Davis | |
| 1946 | Richard Roland | |
| 1945 | Cy Ryan | Northern Pacific Railroad |
| 1944 | Cy Ryan | Northern Pacific Railroad |
| 1943 | Cy Ryan | Northern Pacific Railroad |
| 1942 | Cy Ryan | Northern Pacific Railroad |
| 1941 | Hal Davis | Jas, Griffiths & Sons |
| 1940 | Clifford Clarke | Sexton Clarke Auto Freight |
| 1939 | Steward White | Georgia Pacific Corp |
| 1938 | Edward Pole | R.E. Anderson Company |
| 1937 | Richard Ward | Union Pacific Railroad |
| 1936 | Perry Moore | Foss Launch & Tug Co. |
| 1935 | Herman Tenzler | NW Door & Plywood Sales |
| 1934 | Guy Leonard | TCFB |
| 1933 | Hugh Murphy | |
| 1932 | Bill Donovan | D & NW Railroad |
| 1931 | Alex H. Davis | |
| 1930 | Frank P. Borden | Douglas Fir Plywood Assn. |
| 1929 | Matt H. Newell | Pacific Storage, Inc. |
| 1928 | Matt H. Newell | Pacific Storage, Inc. |
| 1927 | Edward R. Cronkhite | Pacific Match Company |
| 1926 | Edward R. Cronkhite | Pacific Match Company |
