He had also joined the U.S. Navy Judge Advocate General (JAG) Corps as a way to avoid combat in Vietnam and pay for law school. But as his disgust for the war intensified, he found himself burdened with guilt for being part of a military system he abhorred. So he applied to be classified as a conscientious objector. In the summer of 1973, while his request was being considered, he was assigned to Newport, Rhode Island, for military training school. While there he secured a gig at a local club. "I spent the summer going to classes during the day and singing, 'One, two, three, what are we fightin' for?' at night," he recalls. At the end of the summer, the military agreed to grant him status as a conscientious objector.
After finishing his final year of law school (on his own dime), MacDonald didn't bother with the bar exam. Instead he became an itinerant musician. "I wanted to put myself in a position where I had to play music to survive," he says. "I felt that was the only way that I'd ever get good enough to be able to do this. And also I wanted to find out who was out there in the world, what kind of people were really out there. I wanted to get away from the cozy protected people and out into the people that were what I considered more real in a certain way. I was young and arrogant, and that's how I felt. I wanted to test myself against the real world."
Based in Chicago, MacDonald traveled the country mainly by thumb, picking up gigs wherever he could. In 1974, while in New York City, he encountered one of his musical idols. Phil Ochs, the '60s folksinger and protest maven best remembered for his songs assailing the Vietnam War, such as "I Ain't Marching Anymore," was then in the midst of organizing a benefit concert in honor of the recently slain Chilean leader Salvador Allende. The concert was to be a massive event, held at Madison Square Garden and featuring, most notably, Bob Dylan. Hoping to join the roster of performers, MacDonald auditioned for Ochs.
As MacDonald remembers the encounter, Ochs was running the Allende benefit operation out of a cramped office buzzing with people and telephones. Amid the chaos the 26-year-old folksinger played Ochs a song he'd written about the Chilean coup. "Phil squatted down on his haunches, and he listened to me play him my entire song," MacDonald recalls. "People were trying to interrupt him the whole time. They were going, 'Hey Phil, I need you over here.' 'Hey Phil, Baez is on the phone, she needs a hotel room.' 'Hey Phil, McGuinn's in town, he wants to know what to do.' He kept pushing them all away, and he listened to me play my entire song. Then he said to me, 'I'm sorry I can't have you in the show, but I want to thank you for coming by.'"
MacDonald says he wasn't put off by the rebuff. "I was pretty green," he says. "I don't hold it against him that he didn't put me in the show. But I do value the moment that he gave me to play for him very highly." In fact, on the 1998 tribute album What's That I Hear? The Songs of Phil Ochs, MacDonald covers the Ochs song "Pleasures of the Harbor."
Despite his failure to make the cut for the Allende benefit, MacDonald would soon be poised to move beyond the hitchhiker circuit. After spending a few more years on the road, he returned to New York City in 1977, this time for an audience with renowned talent scout John Hammond, Jr. The musicians Hammond had recruited and produced for Columbia records in the past were legendary: Bessie Smith, Billie Holiday, and George Benson, among them. Well before he became famous, Bob Dylan was known as "Hammond's folly" because of his rough-hewn voice and often-cryptic lyrics. More recently Hammond had discovered a young man from New Jersey named Bruce Springsteen.
MacDonald was hoping to be the next unearthed gem. He found an apartment in New York and auditioned for Hammond with positive results. He was set to record some tracks with the producer in hopes of securing a record deal. Before the sessions could take place, however, the almost-70-year-old Hammond suffered a heart attack, which forced him into retirement. "Without his guidance I really was kind of at sea for what to do in terms of walking into a bigtime recording studio and playing my songs," MacDonald recalls. "I really didn't know how to do that."