| Bryan Sanders | Markel Specialty | 2023 |
| Joel Cavaness | Risk Placement Services | 2022 |
| Tim Turner | RT Specialty | 2021 |
| Alan Kaufman | Burns & Wilcox | 2019 |
| Mike Crowley | Markel Corp | 2018 |
| Mike McGavick | XL Group | 2017 |
| Chris Swift | The Hartford Insurance | 2016 |
| Mike Miller | Scottsdale Insurance | 2015 |
| Steve DeCarlo | AmWINS Group, Inc. | 2014 |
| Gregory Case | Aon, LLC. | 2013 |
| Tony Anderson | Ernst & Young | 2012 |
| Robert Woudstra | Farmers Insurance | 2011 |
| Kevin Kelley | Ironshore | 2010 |
| James Weidner | Cooperative of American Physicians | 2009 |
| Stephen W. Lilientha | CNA | 2008 |
| Thomas F. Motamed | The Chubb Corporation | 2007 |
| Anthony Markel | Markel Corporation | 2006 |
| Jack Miller | Zenith Insurance Company | 2005 |
| R. Max Williamson | Scottsdale Insurance | 2004 |
| Thomas Tizzio | AIG | 2004 |
| Brian O’Hara | XL Capital | 2003 |
| Martin D. Feinstein | Farmers Insurance Group, Inc. | 2003 |
| Bernard L. Hengesbauch | CNA Financial Corporation | 2002 |
| Dave Mathis | Kemper | 2002 |
| Joe Stinnette | Fireman’s Fund Insurance Company | 2001 |
| Brian Dupperreault | ACE | 2000 |
| Roxani Gillespie | Barger & Wolen | 2000 |
| Boh Dickey | SAFECO Corporation | 1999 |
| Quill Healey | Marsh | 1999 |
| Heidi Hutter | Swiss Re | 1998 |
| Tom McKernan | Automobile Club of Southern California | 1998 |
| Ed Noonan | American Re | 1997 |
| Gerald J. Sullivan | The Sullivan Group | 1997 |
| Leo E. Denlea | Farmers Insurance Group | 1996 |
| Kathryn McIntyre* | Business Insurance | 1996 |
| Michael O’Halleran* | AON Re Global | 1995 |
| Dean R. O’Hare | The Chubb Corporation | 1995 |
| Philip Engel* | CNA | 1994 |
| John C. Etling | General Re Corporation | 1994 |
| Arthur W. Weiss | Liberty Agencies Inc. | 1993 |
| Bill Bolinder | Zurich | 1993 |
| Roger W. Gilbert | Great American Insurance | 1992 |
| Richards D. Barger | Barger & Wolen | 1991 |
| David R. Carpenter | Transamerica Occidental Life Insurance Company | 1990 |
| Fred G. DuPuis | Independent Insurance Agents & Brokers of California | 1989 |
| William H. Van Leeuwen | National Automobile | 1988 |
| Stephen R. Dach | Jardine Emett & Chandler | 1987 |
| Walter B. Gerken | Pacific Mutual Life Insurance Company | 1986 |
| Bruce Brunner | State of California | 1986 |
| Gleeson L. “Tige” Payne | Ingham, Coates & Payne | 1985 |
| Meno T. Lake | Transamerica Occidental Life Insurance Company | 1985 |
| Harold J. Toso | Mission Insurance Group | 1984 |
| Ron Stever | Stever, Klove & Company | 1984 |
| John M. “Jack” Hayes | Transport Indemnity Company | 1983 |
| Donald M. Johnson | Industrial Indemnity Company | 1982 |
| David I. McIntyre | Freemont Indemnity Company | 1981 |
| George N. Gibbs, Jr. | Stewart Smith West | 1981 |
| Earl Clark | Occidental Insurance | 1980 |
| Richard DeRosa | Mission Insurance Group | 1979 |