Henderson was playing coach of the Elks for more than 20 years starting in 1955, then stayed as bench boss until 1991. As a student of the game with natural leadership abilities, Henderson made the Elks synonymous with softball excellence while his Elks served as a model for other smaller communities to build strong programs.

Brookfield teams won a Maritime Intermediate C championship in 1963, as well as Senior B in 1967 and Senior A Championships in 1968 under head coach Keith Kerr, with Henderson assisting. Brookfield finished third in nationals in 1971 in a tournament the Elks hosted. During the 1970s and 1980s, Henderson was provincial coach, leading junior ladies teams to bronze and silver medals in 1975 and 1976, the best finish for a Nova Scotia ladies team to that time. The Elks under Henderson appeared at six straight nationals starting in 1977, winning the title in 1980. Over 14 years, his Elks were nine times provincial champions and attended nine nationals. As an umpire, he’s worked men’s and women’s nationals.