Jesse Winchester, his life & music

Bob & Jesse (click image for larger size)It was a choice that confronted many young Americans during the 1960s…you’ve been drafted into a war that you vehemently oppose, and the options are pretty bleak: report to the military, go to jail, or flee your homeland for a life in exile. Jesse Winchester faced this very decision after graduating from Williams College. He chose to move north to Canada, and proved to be a talented singer and songwriter. But one condition of going to Canada was the understanding that he could not return to the United States - no personal visits and no professional touring. That handicapped his chances at solo stardom. During his ten years in Canada, Winchester developed quality material, recording some brilliant tunes and writing hits for other artists. When he headed north, Jesse Winchester never imagined that American draft dodgers would be granted amnesty. In 1977, ten years after he left, president Jimmy Carter did just that. Winchester returned to the United States and today lives in Charlottesville, Virginia. That’s where Bob and I met up with him to record a memorable interview.

I had never heard Jesse Winchester’s songs before our trip to Charlottesville, but as a producer who loves music and politics, I have to thank our host for turning me on to his work and his story. He’s a gentle, talented and thoughtful man with a fascinating personal story of historical significance and an excess of musical talent…here’s a guy made to be on this show (and he can dance too!)

I thank Jesse Winchester for his time, his music, his candor and courage. It was a fascinating piece to put together and I hope you’ll find it an engaging listen.

- Dan Bloom

Click here to visit Jesse Winchester’s website,

Click here to see his upcoming tour dates



Video of Jesse Winchester’s ‘interesting’ dance