Past Honorary Trail Bosses

• 1. Junior Cypress – 1997
• 2. Mitchell Cypress – 1998
• 3. Jimmy Cypress – 1999
• 4. Jonah Cypress – 2000
• 5. Little Tigertail – 2001
• 6. Billie Johns – 2002
• 7. Tribute to Jack Motlow – 2003
• 8. Agnes Cypress – 2004
• 9. Esther Buster/Three Generations of Women Cattle Owners – 2005
• 10. Jimmy Smith – 2006
• 11. Frank J Billie – 2007
• 12. Joe Osceola Sr – 2008
• 13. Jacob Osceola Sr – 2009
• 14. Moses Jumper Jr – 2010
• 15. Mary Tigertail & Stanlo Johns – 2011
• 16. Willie Frank – 2012
• 17. Albert Billie – 2013
• 18. Charlie Osceola – 2014
• 19. Johnny Cypress – 2015
• 20. Bert Frazier – 2016
• 21. Henry Osceola & Rudy Osceola – 2018