When he and his brother Dennis moved to London in the 1987 they both joined NYJO, during which time Winston trained at the Trinity College of Music in London.
His background is steeped in music, having been in bands such as the Brand New Heavies, Incognito, Aswad, Jamiroquai, and Courtney Pine’s band. Since 1994 he has been one of four trombonists in the brass section of Jools Holland’s Rhythm and Blues Orchestra.
Winston now lives in Chiswick and has his own recording facility – Red Room Studios – where he has produced many jazz albums. He also co-promotes Jazz @ The Gunnersbury – a popular live big band jazz venue in Chiswick – with another NYJO alumnus, Graeme Taylor.