Born in Louisiana in 1944, Winchester was a southern boy with deep southern roots. His family pedigree traces back to the confederate general, Robert E Lee and to Marcus Winchester, the first Mayor of Memphis. His grandfather was a southern lawyer and his father an Air Force Captain and veteran of World War II. He spent his most formative years in Memphis, during a time of historic musical and cultural change.
At age 22 Jesse Winchester's life took an abrupt turn. It was 1967 at the height of the war in Viet Nam when he received his draft notice for military service. That meant, in all probability, a tour of Viet Nam, something Winchester was against on principle. He was not a anti war activist and had no philosophical or political objections to war, in general, but he was opposed to the war in Vietnam.
He said of that time, “I was very young. .. I was so impulsive and … righteous, you know, like a lot of people are at that age. When you’re that age, there is no tomorrow. I was so mad about [Vietnam] back then; I could hardly talk about it." “I just didn’t feel that I was so right and anybody else was so wrong that I should pick up a gun and shoot him for it,” “And I was so offended by someone coming up to me and presuming to tell me who I should kill and what my life was worth that I didn’t even want to discuss it with them.”
Winchester had options in lieu of military service. He could have obtained a professional exemption like many did, or he could have come up with a health disability like others, but he made a more earnest and life altering choice - he struck a deal with himself to leave forever his Tennessee home, his southern roots and his country of birth.
It was an agonizing decision he recounted years later, “My poor grandfather, whom I loved and admired, was devastated. That still bothers me. He was a gentleman of the old school that believed you should do your patriotic duty." However, Jesse Winchester believed otherwise. "A person ought to do what he believes is right and shut up," he said. So he quietly bought a one way ticket to Montreal Canada.
He arrived in Montreal with $300 in his pocket and no friends in town. "Coming to Canada was the easy part." The hard part came later when you start trying to live your life in line with that decision. That’s when it gets complicated.” “When I first got to Canada I was completely treading water. I didn’t know which way was up. I was in a bad mood all the time.” He said of Montreal, "it is not the easiest place to earn a living singing English songs in a predominantly French city."
He was not alone in his move north as some 30,000 young American's made a similar journey. Most, like him, were pardoned in 1977 by President Jimmy Carter. Jesse Winchester always said that he respected those who served in Viet Nam. He told People Magazine, "The war was like a tornado coming through our lives. People who fought and got themselves shot up for the war believed they were right, and so did I. To me, it's more important how people live with the decisions they make."
A consequence of Jesse Winchester's controversial move north was that the shy, soft spoken southerner became perhaps America's most famous (so called) "draft dodger." Whenever his name was mentioned in the news it included that reference. For his action he was vilified, defamed and branded by the media until the day he died. Upon his death one newspaper still wouldn't let up. Their headline read; Jesse Winchester, Musician and Draft-Dodger, Dead at 69.
Ironically, Jesse Winchester, who's career began as an American living in Canada, ended as a Canadian living in America. He followed his convictions north, never believing he would return. In the end though, love brought him back to America. “I came back to the states because I fell in love with Cindy (Duffy),” he told a reporter. "She lived in Memphis and I couldn’t bring myself to ask her to move to Quebec and learn French." The couple married in 2002 and settled in Charlottesville, Virginia.
Jesse Winchester died in 2014 after a battle with cancer. Upon his death, the New York Times headline described him aptly and succinctly; "Jesse Winchester, Writer and Singer of Thoughtful Songs. I hope that he is also remembered as a courageous man who didn't mind a reasonable amount of trouble.
