Pianist Wynton Kelly played on Kind of Blue, the best-selling jazz album in history, was described by peers as the greatest supporting musician in the genre, and had trumpeter Wynton Marsalis named in his honor, yet he died at 39 in a Toronto hotel room with almost no money. Born in Brooklyn in 1931 to Jamaican immigrant parents, he started piano at four, was forced by his vocational high school to study upright bass and theory instead, played organ in churches and with R&B groups as a young teen, and at 16 made his recording debut on Hal Singer's chart-topping "Cornbread."

This deep dive follows his 1952 Army draft, where he and Duke Pearson lobbied to integrate a segregated entertainment unit and he became a musical director and arranger, his emergence as the most in-demand sideman of the mid-1950s, and the night Miles Davis told a la ...