The mythology of 1960s blues rock says authenticity requires a dusty road and empty pockets. Mike Bloomfield shattered that assumption. Born Michael Bernard Bloomfield in Chicago in 1943, heir to a catering equipment fortune with a 50,000-dollar-a-year trust fund, he was expelled from the prestigious New Trier High School in 1959 for performing a raucous rock and roll song at a school gathering. After seeing Josh White perform, the suburban teenager began taking the train to Chicago’s segregated South Side, where he did not just watch Muddy Waters, Howlin’ Wolf, B.B. King and Sleepy John Estes but got on stage with them and held his own. This episode explores how that unlikely figure revolutionized the electric guitar and why his name is not as widely known as the legends he played beside.

We trace the Paul Butterfield Blues Band with Elvin Bishop, the modal experiments of East-West, and Bloomfield’s piercing Fender Telecaster on Bob Dylan’s Like a Rolling Stone and at the Newport Folk Festival in July 1965, where the crowd booed as Dylan went electric. Bloomfield turned down a permanent place in Dylan’s touring band, formed the Electric Flag for the 1967 Monterey Pop Festival, and walked out of the Super Session recordings after a single day, leaving Al Kooper to finish with Stephen Stills on what became Bloomfield’s best-selling album. The story follows his 1959 Gibson Les Paul Standard, the heroin addiction that hollowed out the 1970s, one last appearance with Dylan at the Warfield Theater in November 1980, and his death in a locked car in San Francisco on February 15, 1981, months before his 38th birthday.

• Bloomfield’s own explanation of the connection he felt between the Jewish and Black experiences of suffering
• What modal music means in practice and how East-West stretched the blues into 20-minute improvisations
• Why he said no to touring with Bob Dylan at the height of Dylan’s fame
• How his tone pushed Gibson to restart manufacturing the Les Paul Standard in 1968, and how he lost that guitar in Vancouver in 1974
• Whether the trust fund that bought his artistic freedom also removed the discipline that might have saved him