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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