Winners
- 2012 - Cot Campbell
- 2008 - Alice Headley Chandler of Mill Ridge Farm
- 2007 - No Award Presented
- 2006 - John A. Nerud
- 2005 - Penny Chenery
- 2004 - The Cella Family
- 2003 - Richard L. Duchossois
- 2002 - Ogden Phipps / Howard Battle
- 2001 - Harry T. Mangurian, Jr. / Pete Pederson
- 2000 - Jim McKay
- 1999 - No award presented
- 1998 - D. G. Van Clief, Jr.
- 1997 - Bob and Beverly Lewis
- 1996 - Allen E. Paulson
- 1995 - James E. "Ted" Bassett III
- 1994 - Alfred G. Vanderbilt II
- 1993 - Paul Mellon
- 1992 - Joe Hirsch / Robert P. Strub
- 1991 - Fred W. Hooper
- 1990 - Warner L. Jones, Jr.
- 1989 - Michael Sandler
- 1988 - John Forsythe
- 1987 - James B. Faulconer
- 1986 - Herman Cohen
- 1985 - Keene Daingerfield
- 1984 - John R. Gaines
- 1981 - Bill Shoemaker
- 1980 - John D. Shapiro
- 1979 - Frank E. Kilroe
- 1978 - Ogden Mills Phipps
- 1977 - Steve Cauthen
- 1976 - Jack J. Dreyfus
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“The two real political parties in America are the Winners and the Losers. The people don’t acknowledge this. They claim membership in two imaginary parties, the Republicans and the Democrats, instead.”
—Kurt Vonnegut, Jr. (b. 1922)