In Search of Dupree Bolton (Part 2 of 2)

I conclude the story of my quest to find a legendary jazz musician who disappeared in the early 1960s

Below I conclude my account of how I found the mysterious jazz musician Dupree Bolton—who created a sensation on the West Coast jazz scene in the early 1960s, and then vanished from sight.

This is an updated and expanded version of an article from my archives.

You can read part one at this link.

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In Search of Dupree Bolton (Part 2 of 2)

By Ted Gioia

[For part 1, click here]

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The Oakland location where Dupree Bolton asked me to meet him was one of those blighted areas of the city surrounding the renovated downtown district. While the city administration worried about recapturing its lost NFL team—the Raiders were in the middle of their twelve year sojourn in Los Angeles at the time—or basked in the limelight of their successful baseball team, the quality of life in this neighborhood wasn’t winning any championships.

I hardly felt safe here, even in broad daylight. But I waited for Bolton for as long as I could. He never appeared. My mystery man had pulled one more disappearing act.

Some hours later, Dupree phoned me with apologies for his absence. “Something came up. I’ll explain it later.”

Dupree Bolton in the early 1960s

The promised explanation never emerged, but the next day our interview continued, and Dupree’s story proved to be every bit as cinematic as promised. “The last 45 years have been a story of drugs, music, and prison,” he told me in somewhat melodramatic fashion. As he set out the details of his autobiography, he proved this was no idle claim.

Our dialogue began as Dupree described the first of his many encounters with the law. “The day before I turned seventeen, I was busted.” He was living in a New York hotel with the dancer Benny Harris. Both were dealing drugs. Dupree’s parents were still trying to find him—“They put ads in the paper and offered a $25 reward” —but Bolton had so far eluded them. When he made his first recordings in 1944, he had used an assumed name to avoid detection. In New York, the following year, he continued to keep as low a profile as possible.

Bolton performed infrequently and supported himself mainly through selling marijuana. Harris precipitated the arrest by selling heroin to an undercover policeman. When they came for Harris, they found marijuana on Bolton. Both were arrested and convicted. Harris served two years for the heroin offense. Bolton’s crime was the lesser of the two, but he served more time because of his age. “The judge sentenced me until my majority, in other words, until I was 21.”

At age 17—a time when most teens are finishing high school—Dupree Bolton found himself institutionalized in a Lexington, Kentucky hospital operated by the U.S. Public Health Service. “It was a bad hospital,” he recalled, “but a good penitentiary. You know, they called them rooms instead of cells.”

But it was not, Bolton explained, a drug-free environment. Even while in Lexington, Dupree and his fellow ‘patients’ had easy access to the marijuana grown there for “scientific purposes.” By the time of his release he had gained an advanced education in the schemes of drug addicts.

Bolton returned to Los Angeles after his release and was reunited with his family. He lived at home and started picking up the pieces of his music career. But his focus on the trumpet was gradually overwhelmed by his dependence on heroin. At this time, he nursed a $20 to $25 a day habit (“Now it would cost you $100 a day,” he told me at our meeting.) The financial rewards of a musician’s life were hardly sufficient, even for a player of Bolton’s talents, to pay these bills. Instead, the trumpeter was “stealing, selling dope, whatever I could.”

Yet Bolton continued to practice and improve during the next two years, even though he rarely performed in public. He was a bebop player in the mold of Dizzy Gillespie and Charlie Parker, but the easiest work for an African-American horn player to find at the time came from rhythm-and-blues bands. “I wouldn’t play that,” he recalled with disdain. “I looked down on rhythm-and-blues. It offered no challenge. I was beboppin’ to bebop.”

Bolton’s hero was Fats Navarro. Navarro had developed an easy mastery of his instrument and played with a warm, clean tone that was almost classical in its purity. Yet, like Bolton, Navarro, propelled his melodic lines with a fire and passion that had no counterpart in the symphonic tradition. “Fats was staying in New York and I saw him just before I went to jail. They used to call him ‘Fat Girl’ because he was a real big guy at the time. But after he got hooked and really into the dope thing, he started losing weight.” Navarro died in July 1950 of tuberculosis aggravated by narcotics use. A promising career had ended at age 26.

The lesson of Navarro’s death apparently had no lasting impact on his young disciple. In 1951 Bolton was arrested again, this time for forgery, and spent the next four years in Soledad. His memories of that period are laced with bitterness. “There was a lot of racial prejudice underneath the surface, and I represented everything the racists did not like. I was a young black who thought he was something. I kept myself clean and neat—the very thing the racists did not want. They expected a black to be slovenly, dirty. I thought I was something, and they really stuck it to me, brother.

“The average guy, even a black guy, who went there and was like they wanted him to be, would do maybe 18 months. I had to do 51 months. I made it, but it was a drag being in the joint that long. So I started doing everything I could trying to get loaded, and there was something there damn near all the time to get loaded on. I started hustling inside Soledad.”

The saving grace of the period was the penitentiary’s music program. “I got a job that didn’t restrict me and I was able to practice every day. I would play tunes, but my main objective was to get down with the mechanics of the instrument. That meant scales and exercises. I would play them sometimes for 12 to 14 hours a day.”

This was the turning point in the trumpeter’s musical development, a time of intensive woodshedding that transformed Bolton from a journeyman player into a formidable trumpeter. Yet even after leaving Soledad in1956, Bolton had little opportunity to make his name—he was soon arrested and another forgery conviction sent him to Terminal Island.

His practice sessions continued there and by the time of his release in Los Angeles in 1959 Dupree Bolton was a stunning player and a potential star. His technique was flawless and his reading ability the envy of many classical performers on the instrument. “In prison I was really making progress and I knew it.” Soon the jazz world would know it, too.

It didn’t take long before word of mouth reports began circulating on the Los Angeles jazz scene of an extraordinary player, who had come out of the blue and was (literally) blowing away the competition. Harold Land and Elmo Hope discovered Bolton playing at a club in Watts. They were looking for a fiery trumpeter who could read Hope’s difficult charts for an upcoming session. They had been told that Bolton was an exceptional reader who could also solo with tremendous passion. After hearing him in person, they immediately enlisted him for Land’s upcoming recording date.

So many years later, the resulting album, The Fox, remains one of the masterpieces of the period. Throughout the 1950s, the myth prevailed that West Coast jazz musicians were soft, they were laid-back melodic players who lacked drive and toughness. If anyone still believed that old canard in 1959, it could have been easily dispelled by listening to this one album. Land and Hope perform with conviction, and contribute some of the finest performances of their distinguished careers.

But the big surprise is Bolton, whose name, only a few months before, had been unknown in the jazz world. This previously unheralded trumpeter played like an established star, with an authority and conviction that turned heads. On the title track he took flight with a speed and energy that’s still astonishing today. I recall one fan describing Bolton’s work here as “a cross between Clifford Brown and a flame-thrower”—a witticism perhaps, but one that effectively captures the sensibility of this riveting performance.

The tempo pushes a ridiculous 400 beats per minute, roughly the rhythm of a machine gun shooting off its bullets, rat-a-tat-a-tat-a-tat. Bolton leaps out of the starting gate like a man shot out of a cannon, and never looks back. He thrives on the near frenzy of the proceedings—indeed, it would be hard to find another trumpet solo that surpasses this one for sheer intensity. The other performances on the album confirmed that Land’s discovery was something special.

Bolton’s legend may only have grown from his marked silence during this period. He refused to give interviews and his past life was a complete mystery. In retrospect, he attributed his attitude to a reluctance to discuss his criminal record and periods of incarceration. “I didn’t want to talk about myself because of my background—prison, using dope, and the rest of it. Whereas now, it helps. It’s kind of like coming out of the closet. But not back thirty years ago.”

Almost as soon as he had arrived on the scene, Bolton again disappeared. He was arrested once more, and sent to San Quentin. He would spend a considerable amount of time in San Quentin during the 1960s. This first time he stayed until 1962. It was a demeaning and disturbing environment—during Bolton’s incarceration, executions were still taking place periodically in the prison’s gas chamber.

“San Quentin was the worst,” Bolton recounted to me, “but I learned quickly how to survive. I learned that if some convicts start fighting with knives, you don’t run over to check out the action. You run in the opposite direction.”

A brief period of freedom in 1962 led to Bolton’s last commercial jazz recordings. He joined saxophonist Curtis Amy on the album Katanga. Bolton contributed the title song and once again proved that he could shine as a forceful and distinctive soloist. A snippet of film from this period also captures him in performance with the Gerald Wilson orchestra. And, a few weeks later, Bolton participated with Amy’s group in a session backing singer Lou Rawls, where even with his limited space to solo, he stands out.

Bolton’s solo here starts at the 1:45 mark.

Some other odds and ends later showed up on the Fireball compilation, released posthumously. Yet Bolton never had a leader date, and after this brief period of activity, his music remained hidden from view for the next quarter of a century.

And why? Once again, Bolton was arrested.

“This is damn near the story of my life—going in and out of the penitentiary.” Arrests for forgery (both for forging checks and prescriptions) and other drug-related offenses were the recurring charges. “I never committed any violent crimes. It wasn’t so much that I didn’t want to hurt anybody,” he admits with candor, “but that I was afraid myself.”

Even back in prison, Bolton continued playing. San Quentin during the 1960s boasted a number of illustrious players, including saxophonists Art Pepper and Frank Morgan, drummer Frank Butler, who had gigged with Miles Davis, and pianist Jimmy Bunn, who had played with Charlie Parker. Morgan would win the Downbeat Critics Poll in 1991 as the best alto saxophonist in jazz, but he once boasted that the best band he ever had was back in San Quentin. Here Bolton continued to practice and refine his craft, but for the jazz world at large he was now a figure from the past.

A 1980 recording with a group of Oklahoma convicts would be his only released session after the early 1960s. Bolton took little pride in this recording. “The people on the record were not musicians. They were just people doing time. I did it because it was something to do.” Dupree characterized the songs as “second-rate-country music.”

Yet Bolton was surprised to see the session listed in Bob Weir’s booklet Dupree Bolton Discography, which I showed him at our interview. Dupree had never seen Weir’s publication before. He asked me if I had compiled the information in the booklet. He was taken aback when I told him that it had been published by a man in England. “Is that right? Man, you never know. I didn’t know anything about it.”

Six years before our meeting, Bolton was released for the last time. He settled in the San Francisco area, where he was living when I conducted our interviews. He participated in a government supervised methadone program. “I don’t like being on it, but it’s saving me.” He had recently started receiving Social Security checks, which supplemented his income from playing on the streets.

After so many years of imprisonment, Bolton savored his personal freedom. But he still managed to credit his periods of incarceration with preserving his life. “I’m still alive, and I know so many guys who are not—because they didn’t go to jail.”

Even with his freedom, Bolton retained a low profile. “There was a guy down in Los Angeles looking for me. He put an ad in Downbeat asking people if they had seen me. A partner of mine—I thought he was a partner until he beat me for one of my checks—wrote him. The guy sent him a tape and asked him to interview me. But nothing happened. My partner didn’t really want to do anything. You’re the first one I’ve talked to.”

Much of the mystery of Dupree Bolton had been solved for me by these interviews. He was no longer an enigma, but had become a tragedy. Even so, I felt that one last thing remained undone.

A few days after our last interview, I brought Dupree to a recording studio, the Music Annex in Menlo Park. Here I accompanied him on piano while he played trumpet. His approach was tentative as he felt his way around the new horn he had borrowed for the occasion. The fire-breathing intensity of his early recordings was apparently gone for good.

On fast numbers, only an occasional phrase reminded the listener of the prepossessing trumpeter of the early 1960s. When we played ballads, he revealed a more delicate approach than I recalled from his earlier recordings, relying on filigreed improvised lines that sought for beauty rather than passion. “Yes, man, I can still play. I can still play,” Bolton asserted. But the recordings, alas, would not live up to the inevitable comparisons with the extraordinary work he had done in his youth.

My photo of Dupree Bolton at the Music Annex in Menlo Park (1989)

I held on to the tapes from this session for some months. But then I did what struck me as the only honorable thing. I destroyed them.

Dupree Bolton should be remembered, I felt, for the greatness of his youthful achievements, not the limitations of his later efforts.

I lost contact with Dupree Bolton after that day in the studio. In the late summer of 1993, I heard through the grapevine that he had died. I tried to get more details, but they were not forthcoming. In early October, I wrote to the Alameda County recorder’s office in Oakland—where Bolton was living when I last saw him—but they wrote back two weeks later saying that they could find no death certificate under that name.

A few years later, researcher Richard Williams tracked down the death certificate in this same office—listed, incorrectly, under the last name of ‘Bolten’. It showed that he had died from cardiac arrest on June 5, 1993. He would have been 64 years old at the time.

His belongings at his death were only a television set. As far as anyone could tell, the deceased did not own a trumpet. According to the county, Bolton was indigent, and he was accordingly cremated at the taxpayer’s expense, his ashes placed in the community crypt at a nearby cemetery.

But if the physical inventory was scanty, the intangible legacy was substantial. Seldom has a jazz musician stirred more excitement with so few recordings. And in the history of jazz, replete with so many tragedies and dead-ends, so many speculations about “if only this” or “if only that” had happened, here was a might-have-been that still rankles me decades later.

The Fox, Katanga—those final documents, should have been, rather, the starting point, not the end, of a glorious career. Even so, Bolton made the most of these sessions, and it is hard to imagine him surpassing these performances, these grand, dramatic gestures that will assuredly keep the legend of Dupree Bolton alive, long after his mystery has been solved.