Bob Dylan and His Tour Manager Had an ‘Explosive and Violent’ Falling out Over a Coffee Shop

Bob Dylan met his tour manager Victor Maymudes when his career was still in its nascence. He was playing tiny shows in New York City, and Maymudes recognized that Dylan had something special. The two became good friends and worked together for years. They had arguments in this time, but the final blow to their relationship came during a vicious fight over a coffee shop. Their decades-long relationship came to an explosive end, and neither man wanted to apologize.

A black and white picture of Bob Dylan wearing sunglasses in front of a window.
Bob Dylan | Doug McKenzie/Getty Images

Bob Dylan met his tour manager in the early 1960s

In 1961, Dylan moved from Minnesota to New York City and began playing shows at small venues in the city.

“My father met Dylan in New York at the [West Village] Gaslight club in early 1961,” Maymudes’ son Jake told Rolling Stone, adding, “He was managing Wavy Gravy and Ramblin’ Jack Elliott at the time. He was a concert promoter and entrepreneur. He was six years older than Bob and way into the counterculture scene. One of the reasons they got along so well is because my old man had a little bit of insight into this new world that Bob was kind of jumping into.”

A black and white picture of Bob Dylan playing the guitar into three microphones.
Bob Dylan in 1961 | Sigmund Goode/Michael Ochs Archive/Getty Images

Before Maymudes was officially Dylan’s tour manager, he drove the artist to shows outside of New York.

“My old man drove him around to coffee shops since nobody else had a car,” Jake said. “There wasn’t an official role, other than buddy.”

Bob Dylan and his tour manager had a falling out over a coffee shop

In the 1980s, Maymudes began investing in real estate for Dylan. He also helped found a coffee shop owned by the singer, attached to his members-only boxing gym. According to Jake, they never advertised the coffee shop as a Dylan-owned business. Maymudes wanted to rely on word of mouth instead of actual advertising. Maymudes’ daughter, Aerie, took over management of the business.

“It was wonderful except for the simple fact that it was still empty and bleeding money with every cappuccino given to the members of the private and exclusive hidden gym,” Jake wrote in the book Another Side of Bob Dylan. “Was it my sister’s fault that the coffee shop on paper was a financial failure? Absolutely, of course it was. Was it Bob and Victor’s lack of oversight and management that fueled Aerie’s lack of experience and her inability to curb the downward financial spiral of the cafe? Absolutely. If you’re going to believe in magic as your pathway to success, then you’d better be ready to pave that road with dollar bills.”

The end-of-year statement showed a business that was hemorrhaging money, and Dylan was furious.

“Bob went into a furious rage that precipitated an explosive and violent firing of Aerie, which Bob personally attended to in full view of my father,” Jake wrote. “My father fought back in defense of Aerie’s unjust treatment, not out of denial of the facts but because of Bob’s sheer abandonment of respect for her. Her removal from management of the cafe may have been warranted, but the way it was done was unforgivable.”

Furious, Maymudes quit and walked out. According to Jake, this may have been the last time the friends spoke to each other without a team of lawyers present. Maymudes sued for retirement funds, and they eventually settled out of court.

Maymudes’ son thinks they would have made amends

Though their long-running friendship ended badly, Jake believes Dylan and his father could have made amends. They hesitated, though, because both felt that the other should apologize first.

A black and white picture of Bob Dylan's tour manager Victor Maymudes sitting on a deck chair in a bathing suit.
Victor Maymudes | John Byrne Cooke Estate/Getty Images
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“Time can smooth out the jagged history between two opposing sides; that negative energy is a bag of bricks that’s being carried and longs to be set down,” he wrote. “Eventually it’s just too much to carry and, even if the damage is not repaired, it can be forgiven. Unfortunately, time has one method for setting permanence: death.”

Maymudes died in 2001, before he could reconcile with Dylan. Jake believes that if he had lived longer, the former friends would have forgiven each other.