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"I actually started painting again on a bet with my father,” McLendon says with a chuckle” said McLendon, son of original Highwaymen artist Roy McLendon, in an interview in 2019.  The bet that changed his path from a graduate of a social work degree, military service, and then working 25 years as a restaurateur?  Seeing terrible impersonated highwaymen paintings at a particular show. “I told my dad that even I could paint better than (that)",  a woman selling what appeared to be Highwaymen art, and that she would never sell those. "He bet me she would, and that if she did I would have to start painting again. To my disbelief, she sold them and I picked up the paintbrush again.”

More than 7 years later McLendon opened his own working studio on 14th Avenue in Vero Beach – the Florida Highwaymen Landscape Art Gallery painting a second generation painter with first generation artistic style and love for the Highwaymen legacy.