.Understanding Complex Beat Figure Neal Cassady

“Myths are stories of our search through the ages for truth, for meaning, for significance.” Joseph Campbell

As a teenager in suburbia in Northern New Jersey in the late 1970s, I was desperate for significance, some sort of a sign that life wasn’t just a cross between Friday Night Lights and The Stepford Wives. America, I believed, was bereft of meaningful tradition. Every “holiday” focused on consumerism and turning the wheel of capitalism one expensive inch at a time. I sought to experience something more meaningful, more transcendent, more damn fun.

In 1977, I serendipitously stumbled upon a dog-eared copy of Tom Wolfe’s The Electric Kool-Aid Acid Test. It was there and then I began to ingest the stories of the legendary, mysteriously cool Neal Cassady and his hammer-swinging antics. Four decades later, I held Cassady’s hammer in my hand, like Thor without the muscles.

Not only is Cassady the Dean Moriarty character in On The Road, the seminal 1957 novel by Jack Kerouac that launched a generation of pilgrims, travelers and seekers, but his own writing, mostly through letters, may have been more influential than anyone has yet acknowledged. In fact, the more I dug into Cassady’s story, the more it seemed like a story about a time traveler, (as I write this, a truck passes by my window with the word “Moriarty” emblazoned on the side) where the traveler creates his own legends across space and time.

Holy Grail

Pacific Avenue has always been the vibrant heart of Santa Cruz. Part Telegraph Avenue, part Haight Street, it is legendary as a bohemian mecca complete with buskers, charlatans and pop-up merchants. On the sidewalk, nestled between the canopied booth selling used vinyl and a group of strident teenagers putting on a mini-EDM concert, is a tie-dyed folding table full of rare out-of-print books, handmade shirts, cards and the previously mentioned hammer. The booth has been setting up on this spot for over a year, and is run by Neal Cassady’s middle child Jami Cassady and her husband of 40 years Randy Ratto. Jami and Randy are helping carry the torch of Neal’s legacy into the 21st century and are the driving force behind a new book on the “Holy Grail of the Beat Generation,” as the book’s subtitle dubs it, The Joan Anderson Letter.

secure document shredding

Written by Neal Cassady in 1950 and lost for 60 years, The Joan Anderson Letter was indeed considered a holy relic of the Beat Generation, and a Rosetta stone document that would show how Cassady’s writing directly influenced Jack Kerouac’s style and direction in life. Which is to say that without this document, On The Road might never have been written, and without Neal Cassady, Jack Kerouac might have written In My Room, instead of setting the literary world on fire.

It was sheer coincidence that the letter came to the attention of the Cassady family. “Randy happened to pick up the SF Chronicle and see an article written by longtime Beat journalist Sam Whiting about the letter being found,” Jami explains from her home in Santa Cruz.

Randy explains the quirky nature of what happened next. “Jerry Cimino, who runs the Beat Museum in San Francisco, got a call from Jean Spinosa, who had the letter, and had Jerry sign an NDA so he couldn’t talk about it. Although Jerry is a good friend, he couldn’t tell us about it. When it was already being displayed, he called us to let us know the letter was in a glass case in his museum on Broadway in San Francisco. Long story short, we sold the letter to Emory University in Atlanta, Georgia and they are able to display it, but they cannot reprint it,” Randy explains.

As fate would have it, Emory University does have a version available online in their digital library. After receiving a call from a Deadhead who said he was going to print it and share it, Jami and Randy got things quickly in motion to have it printed themselves, in proper form, by Black Spring Press Group of London—which had published Jami’s mother Carolyn Cassady’s book, Off The Road, in 1991. There was dissension among some of the surviving Cassady family members about the publication of The Joan Anderson Letter at first, but it was settled pretty quickly.

Contained in the pages of the new book is Cassady’s original hand-typed missive, as well as a companion text that is an easier-to-read version. The words move at the speed of thought; events merge with asides, broad speculation and personal insight. It’s a guided tour through the Bay Area in 1950, complete with the literary hook-up of the century between Cassady and a 20-year-old, 5-month-pregnant Joan Anderson.

To Jami and Randy, the new book is the result of their ongoing effort to preserve Neal’s work.

“Randy and I consider the legacy extremely important,” says Jami, “so our ‘job’ for over 20 years has been to research, promote and share everything we find.”

Return to ‘Grace’

Black Spring is also republishing a second Cassady book that went out of print years ago, Grace Beats Karma, of Neal’s letters to Carolyn and their three children Cathy, John and Jami while he was in San Quentin, serving two potential back-to-back life sentences for selling two joints to undercover cops.

“Angry, happy and guilty” is how Jami describes her dad’s letters in Grace Beats Karma. For the reprint, Jami and Randy are packing it with new documents showing how the arrest happened and what was occurring in their father’s life in 1955. 

“Neal was crazy in love with Natalie Jackson, a poet and jazz singer he met in SF. He had Natalie pretend to be Carolyn so they could withdraw money from the bank and spend it at the racetrack. Neal had a ‘system’ and was sure he could recoup it,” says Randy. What would be about $85,000 in today’s money satiated Cassady’s gambling gremlin, but the deception weighed heavily on Jackson. “After Natalie’s suicide, Neal grew despondent and, according to Carolyn, became a different person,” says Randy. “Mean and sullen.”

After ‘The Joan Anderson Letter,’ the next Cassady reprint project is this collection of letters Neal wrote to his family while he was in San Quentin State Prison. PHOTO: COURTESY JAMI CASSADY AND RANDY RATTO

Grace Beats Karma will focus on the true story of the bust, including all the paperwork from the trial. And if you like courtroom drama, it’s an interesting story. “It seems that Neal wasn’t arrested the first time, after selling the narcs some joints, and they just let him go,” says Randy, sharing some of what he’s researching for the new volume. “The judge threw out the case. One week later the doorbell rang [at their home in Los Gatos] and there were two policeman sheriffs from San Francisco, and so they arrested Neal again. The second trial was at midnight with a new judge and a new prosecutor, and he was sentenced five years to life in two consecutive sentences,” Randy stated.

Key Passages

If Neal Cassady was the kite in the lightning storm, I wanted to be the key. I made my own pilgrimage to the heartland of the weird—Northern California—eventually settling in Santa Cruz, the city of the first unofficial Acid Test, at Ken Babbs’ house in Soquel with the Merry Pranksters and the nascent Warlocks. I found my trippy ground zero. It should be noted that the following week, at the end of 1965, the first official Acid Test was held in San Jose with the newly christened Grateful Dead.

It’s no wonder that micro-dosing has exploded amongst Silicon Valley tech grunts and entrepreneurs. The basin of the South Bay resonates with the first lysergic experiences taken in massive quantities by a large number of curious freaks. And let’s not get started on a certain Steve Jobs’ penchant for hallucinogens. But how does Neal Cassady figure into all this?

Just like Forrest Gump showed up at pivotal moments in history, meeting Elvis, JFK and Nixon, the iconic figure of Neal Cassady looms above, below and sometimes right in the middle of the counterculture’s pivotal moments in time: attending the Six Gallery Reading of Howl (as I write this, I hear that City Lights bookstore owner and kind soul Lawrence Ferlinghetti just died), driving Ken Kesey’s bus with the Merry Pranksters and appearing as a literary counterpoint and sidekick in On The Road. What kind of person would inspire Jack Kerouac, Allen Ginsberg, the Grateful Dead and numerous others to immortalize him in song and prose? Portrayed in numerous movies about Beat history, and sung about by everyone from the Doobie Brothers to Morrissey to King Crimson to Fatboy Slim, who really was Neal Cassady?

Cowboy Neal

Ken Babbs lives on a farm in Dexter, Oregon. At 84 years young, he never misses a day feeding the animals or chopping wood (often posting his chores on Facebook). Babbs co-authored The Last Round Up with Ken Kesey and published  Who Shot The Water Buffalo, a coming-of-age tale set in Vietnam. But most important to this story is the fact that Babbs was a leader of the Merry Pranksters, taking the reins when Kesey was on the lam.

“The first time I met Neal was when we took the Further bus to Manhattan in 1964,” says Babbs. “He was the driver and I was one of the fourteen Merry Pranksters he had never met before, with the exception of Ken Kesey. That must have been around 1962, when Neal just got out of two years in San Quentin and he went to Kesey’s house in Menlo Park.”

It was this event that opened Kesey’s third eye to having Neal drive the bus. “Neal pulled up in his jeepster, and the back end went out. He borrowed tools from Kesey and spent all afternoon fixing the car while talking all the while,” Babbs recalls.  

It wasn’t love at first sight. “He didn’t think much of me at first,” says Babbs. “I gave him hell one day for trying to show us the racing-car four-wheel-drift while driving the bus and throwing us all around. He called me a tourist, which was his way of saying I didn’t come up through the Beat and Bohemian ranks.” Which is true, as Babbs was too busy being trained to be a helicopter pilot in the Marine Corps to sip red wine and smoke cigarettes in dingy cafes all day.  

As time went on, they got to know each other better and eventually became good friends. And that time together was life-changing for Babbs. “Spend time with Neal and he definitely influenced the way you looked at things, from figuring out the one-thirtieth-of-a-second of time it took for your brain to react to something that you were trying to do, to working at being a better person, one who would help another out and try to bring people out of their shells and groove,” says Babbs.

The Spark

Things that are lost for 60 years are usually not found, but when they are, it’s astounding. The rumor was that the Joan Anderson letter had had blown off a barge into the water; to have it suddenly pop up borders on the supernatural. And it really is an important document. Without it, says Jack Kerouac scholar Dennis McNally, there would never have been On The Road and the huge role it played in American counterculture.

“Janis Joplin read On The Road and then hitchhiked from Texas to San Francisco. Jerry Garcia only had to take the #14 Mission bus up from Visitacion Valley, but found the book to be a ‘germinal moment,’ says McNally. “But there would not have been On The Road without the Joan Anderson letter. It was one of the elements that kick-started Kerouac into looking for a different way of writing than he had attempted up to that point. Jazz, of course, was equally important. But the letter crystalized something in him and he rose to the occasion.”

Jerry Garcia called Neal Cassady “the 100% communicator,” and, “a 12th-dimensional Lenny Bruce.” “It’s been written and talked about that Neal Cassady perceived and communicated more than the average person. He could run into somebody after a year, and resume the conversation they were having a year ago, without a gap,” says McNally. “He could famously carry on five conversations at once.”

In today’s cancel culture, a character like Neal Cassady could be dismissed as just another example of male toxicity. But that would be missing the mark, and falling into the void. In the Joan Anderson letter, you have to understand the texture, atmosphere and crossroads in time where Neal was coming from to appreciate the letter. The letter violates many modern mores, it is hypersexual, it could trigger you, you can claim it’s misogynistic, but it’s also too weird for a lot of people to give it justice. Luckily for me, “weird” is my wheelhouse.

“Neal was a forerunner of omnisexuality, he was highly sexual,” says McNally. “Neal was the reverse of monogamous. For most people, having one relationship is sufficient. Look at On The Road where he’s going out for cigarettes and returns two weeks later. In the interval he gets married. Beyond crazy. So, much of this was extremely painful for Carolyn, but she loved him all through it and beyond. Carolyn’s basically normal middle-class American expectations had shattered so many times that it was painful. To make him just a hero is risky. I won’t call it narcissistic, but he was pretty obsessed with himself and getting what he wanted. And he didn’t always necessarily look out for everyone around him,” McNally adds.

Neal Cassady died at 42 from a wild past, a meteor shooting across the sky. “He used more of himself, his body and his mind then the specs of the model would permit,” McNally suggests.

Neal Cassady was a master at taking the potential in the present moment and making it manifest, being a walking affirmation. He was not waiting for something or someone else to do something, as he was always doing it and showing by example how you could live more intensely in the fleeting present moment. This idea can endlessly inspire people, like myself, who have no idea what it was like to live in the 1950s or ’60s. “The worst mistake people make is that ‘Neal was special, that he was a mythical superhero, he was different than me and my friends, because we were born at the wrong time.’ Neal would have no patience for that thought,” says Steve Silberman, a scholar of the Beat and hippie generations.

Today, everyone is looking for a hero. Being a hero is a billion-dollar business—slapping on a cape and a mask and saving the world is the name of the day. The bad thing about superheroes is their heroics are fiction, contained within the frames of page and screen. But Neal Cassady was flesh and sinew, chiseled jawline and chemically enhanced blood—but mortal, and with that, less than perfect. Being less than perfect was finally something I could see in myself.

To order “The Joan Anderson Letter,” contact Jami Cassady at [email protected]


  1. Every time I see your dad’s picture I can’t hold back the teardrops, just fantasizing our parents hanging out together and your Dad working with mine and just imagine what a wonderful beautiful experience they had together in that bookstore can’t we just bring them back for one more trip? our Dads free speech night within all those cats!I love you guys stay strong and be beautiful like you are and keep keeping up the good work!

  2. I wish all of us could be more Neal Cassady. What an incredible force of nature. Thank you Jami and Randy for continuing his legacy. Sending love from the UK.


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