He attended Interlochen Arts Academy, then studied music theory and composition at the University of New Orleans. While there, he won a scholarship to study Czech music at St. Charles University in Prague, and has also studied with avant-garde composer "Blue" Gene Tyranny. After his tour van was burglarized in Louisiana, Winslow-King found himself back in New Orleans, and he soon opted to stay, playing blues and folk music on the streets of the Crescent City as an accompanist to jazz singer John Boutte. Winslow-King has also written scores for theater and film productions, worked as a music therapist with the Institute of Applied Human Dynamics in the Bronx, New York in 2004, and taught music at the La Velle School for the Blind. After settling in New Orleans, Winslow-King co-founded Earthwork Music and performed on the label's albums, releasing his self-titled debut in 2006. In 2009, he followed it with Old/New Baby, issued through Fox on a Hill Productions. The Coming Tide appeared in 2013, released by the respected roots music label Bloodshot Records. Winslow-King and his music partner (and spouse) Esther Rose maintained a busy touring schedule, headlining at small venues and opening for the likes of Taj Mahal, the Rebirth Brass Band, Chris Thile, and Jack White. In the fall of 2014, Winslow-King released his second album for Bloodshot, Everlasting Arms. In October 2015, Winslow-King and Esther Rose divorced. The experience informed his 2016 album I'm Glad Trouble Don't Last Always, which he dedicated to her, adding,"Thank you for helping me to understand the true nature of love and loss." ~ William Ruhlmann