| 2014 | ||
| 2013 | Greg Worrell | Leprechaun |
| 2012 | Michael Belcheff | Virgin Islands Pirate |
| 2011 | Sheniqua Robinson | Miss U.S. Virgin Islands |
| 2010 | ||
| 2009 | Miss Judith | |
| 2008 | ||
| 2007 | Rev. John McLoughlin | pastor at St. Patrick’s Church |
| 2006 | Mary Simpson | Travel Agent / Business Owner |
| 2005 | Lee Morris | Educator |
| 2004 | John “Big Beard” Macy | Boat Owner / Charter |
| 2003 | Eddie Donoghue | Author Historian |
| 2002 | Angel Santos | Police and Fire Chiefs |
| 2002 * | Roberto Santos | Police and Fire Chiefs |
| 2001 | Richard “Disk” Hyle | Businessman |
| 2000 | Jim Byrne | Businessman / Real Estate |
| 1999 | Cielo Maldonado | St Croix Majorette’s |
| 1998 | Oscar Henry | Commissioner of Agriculture |
| 1997 | Mary Edwards | St Croix Animal Shelter |
| 1996 | Cecil Benjamin | C’sted Administrator |
| 1995 | Bill Bass | Musician / Composer |
| 1994 | ||
| 1993 | Jessica Tutien | Mayor of Gallow’s Bay |
| 1992 | Lloyd Canegata | Fire Chief |
| 1991 | Betty Sperber | King Christian Hotel Owner |
| 1990 | Raphael S. Munchez, Sr. | Retired Pueblo Dist. Mgr |
| 1989 | Harry Gross | At The Office |
| 1988 | Sue Salter | F’sted Businesswoman |
| 1987 | Jerome “Jerry” Dodge | Retired WAPA |
| 1986 | Alva McFarlane | Police Comm. |
| 1985 | George “Speedy” Washington | Police Comm. |
| 1984 | Oswald “Owen” Schjang | Businessman |
| 1983 | Bob Owens | Softball Organizer |
| 1982 | Captain Weeks | Businessman |
| 1981 | Ruby Rouss | Senator |
| 1980 | Sir Aubrey Saunders | “Pigs Ear” Businessman |
| 1979 | Monsegnor Kelly | Priest |
| 1978 | Sidney Lee | Senator |
| 1977 | Ron DeLugo | Delegate to Congress |
| 1976 | Earl “Pop” Williams | Retired Army m/sgt |
| 1975 | Juan Luis | Lt. Gov. |
| 1974 | Attie Ottley | Lt. Gov. |
| 1973 | Stanley Farrelly | Island Administrator |
| 1972 | George “Bagoon” O’Reilly | Radio Personality |