Ch. 5 - Uncle Benedict: One Degree of Separation from the One Percent of the One Percent. Or How Much is Enough?

Below is chapter 5 from Ken’s forthcoming book, How Did I Get Here? A Memoir of the Baby Boom Generation.


I was at the top of Manhattan, in the penthouse of Uncle Benedict.

We were sitting on European masterpiece furniture, sipping wine and chatting amidst magnificent objets d’art from the Belle Epoque. I sat beside an Art Nouveau mahogany grand piano. A twin was in a French museum.

The room glowed with Louis Comfort Tiffany glass – actual Tiffanies, table and floor lamps, at least 10, and a chandelier too. They dripped with grapes, dragonflies, spider webs, lilies, and wisteria. A gleaming Tiffany glass panel covered an entire wall. I had seen something like it in the American Wing at the Met.

On the other walls were favorite pieces from Benedict’s collection of central European Expressionist art. Those paintings by Gustav Klimt, Otto Dix, Max Beckmann, and George Grosz could have hung in any museum. Tormented faces and turbulent scenes from the Weimar era were there for my intimate viewing pleasure.

The penthouse was on Riverside Drive, where Benedict had bought the thirteenth floor, once owned by William Randolph Hearst. With air rights to build up, he had constructed a three-story palace in the sky, with floor-to-ceiling curved windows facing the Hudson River and vast terraces that overlooked the city in all directions. Architectural Digest acclaimed the stunning creation in a gorgeous spread.

Like everything Benedict had, the penthouse and its contents were unique and exquisite, the finest in the world. I inhabited it for four enchanting days. I was awed. And, oddly, I felt comfortable, as if I belonged.

This was Stephanie’s and my most successful visit with her Uncle Benedict and his young wife Jayne. We stayed for a vacation in the adjoining guest apartment a floor below. I have a photograph of Benedict and me in Riverside Park, with our heads in the branches of cherry trees, our faces laughing in a sea of pink blossoms.

Benedict’s opulent life made me giddy. One evening we had dinner at a hot new restaurant in the Meatpacking District. Dining out with Benedict was often difficult, shadowed by that lurking question of who pays what, but this time it was fabulous. From the moment we entered, the restaurant understood that Benedict was our wonderful rich patron. Waiters, busboys, sommelier, and manager fluttered about our table, cheerily bantering with Benedict, attending to our every wish.

I cannot recall one bite of the excellent meal, but I do remember a waiter shaving truffle onto Jayne’s salad, $100 a swipe, and Benedict urging, “More. More.” Hours later when we departed, the restaurant staff formed a ceremonial guard as we paraded between them to the door, and they gave us each a gift, a pastry, something delicious that had not been on the dessert menu.

Then back to the Upper West Side, up the private elevator to the penthouse, for a last drink amidst the glorious art before Stephanie and I descended the private stairway to the guest apartment. But I was not ready to sleep. I wanted to daydream about Benedict’s splendid world.

The highlight of that vacation was my discussions with Benedict about his latest acquisition, a 1910 painting by the Austrian artist Egon Schiele, Woman With Homunculus. It was a vivid watercolor of a sensual nude young woman, seen from the back, her face turned seductively to the viewer, an alluring eye, a flushed cheek, hip at a suggestive tilt, with an incongruous deformed child-like creature clinging to her side.

For days Benedict and I dissected Schiele’s meaning, with the alluring nymph and the grotesque child gripping her torso: erotic young beauty and disturbing inevitable decay. We discussed the sale by fellow collector Ronald Lauder for cash to acquire Gustav Klimt’s masterpiece Adele Bloch-Bauer for his Neue Galerie. Benedict recounted his purchase machinations to out-fox a rival German collector. We considered whether this stunning addition completed Benedict’s extraordinary collection.

Benedict usually didn’t talk about his wealth with me, but he was infatuated with this painting. Our discussions were so intense that, in an exuberant moment, he told me his purchase price in the millions and hundreds of thousands of dollars. I was thrilled. I too loved that painting.

On the flight home to San Francisco, I mused over why this visit with Uncle Benedict had gone so well. I thought I knew the reason. Benedict was difficult, particularly about money and anyone who wanted money from him. Long ago, when we were poor, I had offered Stephanie a strategy for our dealings with him: “Want nothing. Expect nothing. Ask for nothing. Just be ourselves and enjoy his company.” That became our Benedict Rule.

The Rule had been our guidepost over years with Benedict. “Be normal,” was my mantra. And, lo, recently Stephanie’s mother, Benedict’s sister, had reported to us, “Benedict considers you his friends. He said, ‘Stephanie and Ken don’t want anything from me.’”

“That’s right,” I thought, as we soared west. My mind wandered contentedly through the successful visit and our sensible approach to Benedict. And then my ruminations stopped, abruptly, at Woman With Homunculus: the alluring young mother glancing at me, the mysterious child, Benedict’s derring-do in acquiring them, our intimate discussions about art and commerce, the millions of dollars. I thought, “Does Benedict understand my appreciation for that painting?”

“Yes,” I answered myself.

“And maybe,” I careened on, “Benedict will leave me the painting when he dies.”

That wish haunted me for weeks. How would this masterpiece fit in our modest home? Where to place it among our treasured paintings by friends and local artists. How to hang it? Insurance? Security? Loans to museums? And how to sell it when the time comes? I had no answer for any of these demented wonderings, nor any sane reason why Benedict would give me Woman with Homunculus.

I had broken the Benedict Rule, again.

* * *

Benedict was tall and slender, crackling with energy like a loose live wire. He spoke in sharp reedy New York tones and he was aggressive, jabbing at you with words. He could charm you too. And he could dominate a dinner table; pontificate, actually. Surprisingly, he also could listen carefully, and he was a shrewd appraiser of others.

Dealing with Benedict over the years, I felt “seen,” at least about money. He understood my financial situations. I learned that around Benedict you must know your own purposes and be true to your own passions and rely on your own income, and then he might respect you. He might even help you.

I was dazzled by the saga of Benedict as a self-made entrepreneur. Born in 1929, starting with nothing, once reduced to collecting quarters each evening from his laundromats, he began making big money in the 1970s when his real estate company arranged innovative financing for the lightning-fast expansion of retail behemoths Walmart, K-Mart, and Kroger, feeding the massive consumption of my baby boom generation. He worked with the legendary Sam Walton in Walmart’s early growth years, for fees of unimaginable millions, and at one point Walton paid for Benedict’s services with ownership interests in actual Walmart stores. From there, Benedict financed his own commercial real estate projects. When I met Benedict in the 1980s, he was a real estate mogul, a legendary titan among American shopping center developers.

While I was challenging capitalism as a radical graduate student at UC Berkeley in the late 1960s, as I studied revolutionary working class movements and socialist theory, Benedict began collecting art. He had detailed knowledge of each purchase, and a personal reason for acquiring it. Benedict explained his idiosyncratic attraction to a 1915 Ludwig Meidner apocalyptic painting, titled The Incident in the Suburbs, like this: “That standing figure, that’s me. I’d just become active in the real estate business, I didn’t know what I was doing, I was scared stiff but I was pushing down the competition – that’s the guy on the floor – and all around are the buildings I’m trying to finance, shaking.” The Yiddish term, shakher makher, wheeler-dealer, comes to mind when I imagine younger Benedict building his fortune through raw capitalist combat.

Later there was much more to Benedict’s empire, once built, no longer shaking: enterprises, investments, real estate, homes, art collections, and philanthropy too. I estimated Benedict’s fortune at a billion dollars. Or was it half a billion?

Of course, I knew that Benedict’s life and accomplishments represented everything I opposed. My book on Joe Rapoport, for example, told the story of a Jewish immigrant Communist who I admired for his lifelong struggles to build trade unions and a socialist society with an equitable division of wealth for fellow workers. I saw no equity in Benedict’s world; only accumulation of vast wealth by Benedict.

I also knew that Benedict had his own messy complications – family, health, business, even money. “God knows,” Benedict once told a reporter, “money tainted ninety per cent of my life.”

It was difficult for me, a radical and a socialist, to feel sympathy for Benedict about money problems or even to believe that he had money problems. Peering into his life from the nearby outside, I was transfixed by the aura of Benedict’s fabulous wealth.

That was Stephanie’s Uncle Benedict: in the one percent of the one percent, larger than life, and just one degree of separation from me.

Benedict was a problem for me: money, money, money, money, money.

* * *

When Stephanie and I took up together in 1980, I was 35, a writer and part-time teacher, with a net worth in the hundreds of dollars. I was a snob, too, who never would have set foot in some tacky Walmart store with its cheap goods for mass consumption, the cornerstone of Benedict’s fortune. What’s more, I opposed Walmart for its oppressive employment policies and its crushing impacts on small retail competitors in the communities it invaded.

Though poor, I was confident. I came from a modest north Chicago suburb, Skokie, that my parents had reached after Depression childhoods in the Jewish immigrant ghettos of the Chicago West Side. Their parents, Eastern European immigrant settlers in the early 1900s, had lived by their hard labor and wits through pushcarts, sweatshops, and neighborhood stores. My father had struggled through the Depression for a college education at night schools, and became a chemist. Then my parents rode the wave of postwar prosperity with their generation into the tidy grid of new homes in the suburb Skokie. I was propelled farther upward together with my baby boom friends by our parents’ generational ascendancy.

My teenage notion of affluence was the larger homes on the quieter, leafier winding streets of tony suburbs to our north. My high school plan was to own one of those dignified homes. I left for the University of Wisconsin-Madison in 1962, with the career goal of becoming a tax attorney and a certified public accountant.

Two professions? Sure. I knew I could achieve anything because I was smart, hard-working, and on track. My childhood in 1950s and 1960s suburban America promised to reward these virtues with upward achievement and prosperity, perhaps even wealth.

But I went off track without even knowing it. In the youth upheaval of the 1960s, I joined the radical student movement for civil rights, stopping the Vietnam War, and ending poverty for the working classes. To be sure, I was an ambitious radical who intended to obtain a Ph.D. degree and become a university professor, a radical who sought academic accomplishment through study of insurgent working class movements, a radical who had faith in a future that somehow would include wealth.

Those twin drives, rebellion and academic achievement, impelled me to California in 1966. I was drawn by the great student uprising in the Free Speech Movement and by graduate study in history, both at the preeminent University of California, Berkeley. I gave no consideration to law school or accounting. I stopped thinking about money for many years, except as needed to sustain my California journey.

As I made my way through the UC Berkeley Ph.D. program, I wandered, virtually penniless and without worry. I took off two years to teach at a North Carolina Black university, where I became absorbed in my students and the Civil Rights Movement. Back on the Berkeley campus in the early 1970s, continuing my history graduate program, I tried life as a hippie and explored the counterculture. Next was rural life, two years writing my Ph.D. dissertation in a cottage in a little beach town where the Russian River meets the ocean. I joined Chamokome, a nearby collective ranch in the hills of Sonoma County, launching my lifetime participation in our version of a socialist community.

Then I went entirely off track, this time off the track to become a professor. Eleven years after I began graduate school, in 1977, I obtained that Ph.D. degree. With my employment ticket at last in grasp, along with the promise of a regular paycheck, I immediately jettisoned that professor career and its plodding salary. The actual conclusion came with a job opportunity at Lake Forest College, a lovely liberal arts college in one of those tony north Chicago suburbs where I once aspired to be a homeowner. But now that job, I thought, led straight back to where I started in Skokie, a bland suburban life with a predictable academic career and the once desired large home on a leafy curving street. Not for me, not then. I had changed. I had become a radical, a hippie, a writer…anything but an employed professor.

With my optimism from the Fifties and Sixties, anything seemed possible. I followed my bliss, toward poverty. I remained in Berkeley, calling myself a free-lance popular historian, working on a book about Jewish chicken ranchers. Yes, Jewish chicken ranchers…left-wing Jewish chicken ranchers...a renowned community of them, including the Communist trade union organizer Joe Rapoport, who became the subject of my simultaneous second book project. Through those books I intended to tell the great saga of American immigration and assimilation, and, while I was at it, win the Pulitzer Prize for history.

My new career title, free-lance popular historian, told it all. No workplace. No salary. No recognizable job. And virtually no income. I hustled for writing grants and temporary college teaching gigs. Others might have said my career path was downward mobility to wandering part-time teacher, that is, to academic migrant worker.

Nonetheless, I did well with Benedict when we met in the early 1980s, just after I published my first book about that Communist labor organizer Joe Rapoport. Although I lived hand-to-mouth, I had a commitment Benedict admired: writing books about those left-wing Jewish chicken ranchers. Benedict, like me, saw this little community as historically significant, telling a universal tale about American immigration. He admired Joe Rapoport for his consistent purpose and integrity in a lifelong struggle to organize workers and build socialism. Benedict considered himself politically liberal, a sympathizer with these socialist and communist chicken ranchers, nothing I took seriously. Although Benedict and my chicken ranchers were an unlikely mix, those books, which may have brought me pennies an hour for my years of labor, were valuable currency in my dealings with Benedict.

Benedict’s respect for my writing led to my first nutty fantasy: “Why doesn’t he just give Stephanie and me a million dollars?”

I remembered the 1950s television program The Millionaire. In each episode, philanthropist John Beresford Tipton, Jr., ensconced in his huge estate Silverstone, through his omniscient and magnanimous interest in other people, and his vast old wealth, would arrange for an anonymous one million dollars gift to a recipient with 1950s type strivings for fortune, happiness, or good works. I considered my chicken rancher books close enough to be worthy of such a gigantic award. Through each encounter with Benedict in the 1980s, I daydreamed about him making me The Millionaire.

Any sober reflection would have concluded that Benedict was no John Beresford Tipton, Jr., and no million dollars was coming my way. However, Benedict and sober reflection did not mix in my mind. When Stephanie and I married in 1985, Benedict gave us a wedding gift of $1,000, which was a lot of money for us at the time, and we were grateful. But, before the wedding, it seemed to me as if anything could happen in my world of beneficent acts, including the much-needed, would-be-greatly-appreciated, life-changing million dollars. But Benedict knew the value of a dollar, and in the end his gift was just generous.

I could not complain about that.

* * *

Benedict’s titanic wealth and my meager resources became an unsettling combination. Something had to change, and it would not be on Benedict’s end. There was a restaurant meal, my first with Benedict, during a 1980s San Francisco visit. We were at a chic bistro with 10 at the table. The check came, handed by the waiter to Benedict, of course, and we all left it to him to pay this infinitesimal charge. As he pulled out his credit card, I overheard Benedict complain that he had been travelling for weeks, visiting many family and friends, and he had paid every bill at every restaurant. Indeed, this was no John Beresford Tipton, Jr.

I felt shame. I imagined having grabbed that check and picked up the tab without fuss. But, one problem: I couldn’t afford it. And, anyhow, who the heck was I to take Benedict out for dinner?

That meal revealed my dilemma in the early 1980s: how to pay my own way. Benedict, describing his wife Jayne marrying into his fortune, once observed, “Upward mobility is so much easier.” I knew Benedict got it right. Approaching 40, I was beginning to realize that I was on the other trajectory: downward. I came from suburban comfort, but I still was graduate student poor. This poverty had become uncomfortable. It was becoming permanent.

“Money talks,” they say, but during my years as a student rebel and radical historian, between the early 1960s and the early 1980s, not to me. When money did resume speaking to me in the Eighties, or when I resumed hearing, the message was simple: “You have none. Others have plenty.”

During the years of the student rebellion, I didn’t think much about money. When I did, I criticized the unfair division of wealth for the working classes. And I had contempt for the gross consumption of the middle classes where I began.

But money began making me miserable in the 1980s. It was an era that celebrated wealth and consumption. It was the era of the Yuppies, Young Urban Professionals, a new narrow slice of my baby boom generation known for their individualism and self-preoccupation, aggressive work ethic and drive for wealth, affluence, expensive tastes, and forcing out residents from old neighborhoods they gentrified. It was the era of corporate-raider inside trader Gordon Gekko from the film Wall Street. Everyone knew how Gekko summed up the Eighties: “Greed is good.”

1981 is when the rock band Talking Heads released their song “Once In A Lifetime,” also the title of a book about the inspiration for their songs. The song’s protagonist, in an existential crisis, asks “How Did I Here?” with his conventional trophies of mainstream success: a beautiful wife, a beautiful house, and a large automobile.

The song continues: “MY GOD…WHAT HAVE I DONE?”

My situation in 1981 was the exact opposite of the Talking Heads’ song. My “How Did I Get Here?” meant how was I left behind? How do I return to the mainstream. How do I win my trophies of success? I needed some greed.

I was living in the greedy Eighties, but as a throwback from the rebellious Sixties. I was spooked by my predicament: itinerant teaching jobs, uncertain income, living on a pittance, no prospects for improvement. This scraping by had been fine in the Sixties. But now approaching 40 in this new era of wealth and consumption, I was embarrassed and envious.

Was I ready for that job as a history professor at Lake Forest College? I explored a return to the academic world, but everything conspired against me: an academic job market with ever scarcer jobs, and brutal competition from ambitious younger baby boom Ph.D.s searching like me for a start up the ladder to tenured full professor.

Okay, I realized, my opportunity to become a professor had passed. It happened before I even recognized that I had let it go, when I chose to do those books on chicken ranchers instead of finding a university teaching job and turning my Ph.D. dissertation into a book. Now I had to move on.

Actually, I felt more relieved than disappointed as I realized what I had done. In fact, I no longer wanted to be a professor.

Now, I wanted more money than I could earn as a professor. I thought I had the brains and competitive drive to get it. How much more? I didn’t know. What was possible? Benedict had whetted my appetite with his fantastic example of what was possible, with his astonishing illustration of the Yiddish idiom “The appetite grows with the eating.”

Eventually, I did find my way, and it was not an easy way. After two years in a confusing search for a new vocation, I returned to my original path, before my 1960s and 1970s detours to become a professor and then a free-lance historian. In 1983, I enrolled in law school, just as I had planned in the Fifties, my high school plan.

My rebellious odyssey through the Sixties and Seventies was at an end. My poverty, once the temporary condition of graduate study, had threatened to become permanent, while the world around me was barreling along to wealth. It was intolerable. It was time to go straight.

I started over, at the bottom again: a first-year law student.

* * *

As a new lawyer in 1986, at age 42, I had changed the game. Now no one cared about my student radicalism or refusal to pursue a job at Lake Forest College or years studying chicken ranchers. I had a clean slate in a moneymaking profession.

My relationship with Benedict changed with my new law career, but not for the better. Benedict, once a struggling attorney, offered a head-spinning bleak perspective: “Lawyers are only paid for their time,” he informed me. “Time is limited.” He had contempt for attorneys as moneymakers.

An entrepreneurial new attorney, I was excited when Benedict requested my legal advice on a family matter involving a California contract. Benedict was a whale-sized client for a new attorney, and I happily imagined grabbing his legal business for commercial real estate. I advised him about the contract, and he followed the advice. But when my bill arrived, he refused to pay, indignantly complaining that family help should be gratis.

I was baffled. I thought that law practice, unlike writing history, was all about pay for work. Was I too eager? Too money-grubbing? Was I not ready for whale hunting? That ended my legal work for Benedict.

Just as Benedict had warned, I found no immediate riches in law practice. The first years, we struggled to pay our bills as I pursued this new route away from my penniless historian detours, and Stephanie was on her own long march toward a career as a psychologist. These roads were not paved with gold, and I worried about money. Expensive private schools for our daughter, sure, but never a new car. Buying a first house, a true fixer-upper, was a struggle that required help from generous parents. At one low point, I told Stephanie we should stop subscribing to magazines.

We first stayed with Benedict in the 1990s. I had become an established attorney and we could afford a luxurious long weekend vacation in New York City. Benedict then lived on the Upper East Side, where he had combined two large Park Avenue apartments into a huge full-floor residence. He had recently married Jayne, and was building the great penthouse on the trendier West Side. He was on the phone nonstop, berating his architects and squelching real estate predators all around. I knew who was the most dangerous predator.

In his study, I saw a photograph of Benedict smiling so broadly he could have floated up out the frame. Standing next to him was the Big Dog, Bill Clinton. Turned out, Benedict was a Democratic Party donor, a big one. Side-by-side in the picture, Benedict was almost as tall as Clinton. “How,” I wondered, “did a Jewish real estate financier become so tall?”

At 5’7”, I would have been the short guy in that impossibly expensive photo. During the visit I felt smaller yet, as Benedict grilled me on why I was not yet a law firm partner. Benedict could do that – torture me about insufficient professional accomplishment – as a prerogative of his fantastic wealth. Benedict once explained to me that his wealth allowed him to make his own rules of behavior and tell others to buzz off.

I dodged and squirmed with Benedict’s partnership question, because, notwithstanding my considerable skills as a litigator, the simple answer was that I did not generate enough business. I was no fearless entrepreneur, like Benedict, and Sam Walton would not have entrusted me with his legal business. At long last I had achieved a comfortable middle class living through law practice, but it earned me no credits with Benedict. He admired my chicken ranchers book more than my legal earnings.

I did have one good moment with Benedict while practicing law, and, surprise, it occurred with another meal. In the late 1990s, Benedict and Jayne visited San Francisco for Passover with family. I felt expansive at that time, with a thriving law career and a healthy income based on long work hours and profit from the clients I recruited, though not the elusive partnership position. Stephanie was now launched as a psychologist, and we enjoyed two professional incomes. We decided to host this family Seder.

A home visit from Benedict was like the king stopping by, requiring extensive preparations for the very best we could do. Stephanie and her sister Kay planned and prepared the royal feast. My contribution was conducting the Seder. We worried, we scurried, and it went as planned: the warm socializing, the streamlined Seder, the thoughtful discussion of Jewish exodus from Egyptian slavery, and the sumptuous meal.

Benedict was moved, and he profusely thanked me at the end of the evening. Benedict was a sexist of the old-school variety. He just did not think about contributions by women. So, nothing Stephanie and Kay had done for the Seder – and, actually, that was just about everything – registered with him. Not a word of thanks to them. At the door, walking Benedict out, I bubbled over with gracious pleasure at his gratitude for my hosting this great family event. For those moments we were two bros, Benedict and Ken. And Stephanie and Kay, each with her own complex history with Benedict, were furious…thankfully, at him, not me.

Following the Seder, Benedict tried to help me leave the house – my albatross – where we had staged the event. It was our first home purchase, made with friends, a Victorian three-flat right on Haight Street. Stephanie and our daughter Julia loved living in this cutting-edge San Francisco neighborhood, famous from the sixties counterculture, with gritty coffee houses and bars, head shops and retro clothing stores, and a kaleidoscope of hippies, hipsters, artists, students, druggies, and pioneering upscale families in old Victorians, us among the latter.

I came to detest our building as an irreparable slum in an urban frontier that never would fulfill its promise of gentrification. This was confirmed to me one Sunday afternoon, finding a tribe of stoned young people – fellow descendants from the Sixties – camped on my front sidewalk, selling my sixties Marxist history books they had stolen from a storage room under the front stairs.

I viewed that house as beneath my hard-won station as a successful attorney, a cruel reward for my epic middle-aged journey to law practice, where I had tried to correct my career course after those youthful detours to professor and free-lance historian. This Victorian money pit did not reach my high school goal of a larger home on a leafier curving street in the farther northern suburbs of my Skokie childhood. It did not approach my generation’s grand homes for smaller families with ever more bedrooms, bathrooms, recreation rooms, and spacious kitchens like luxury living rooms. Granted, our Haight Street flat was hip, but I was no longer hip.

Stephanie was a challenging mate for my journey toward property acquisition. She was professionally ambitious, but when it came to money she had a pre-capitalist view: she just wanted to know how much she needed to earn for the life we wanted to live, rather than pursuing open-ended accumulation. Stephanie tempered my wants with her simple concrete question that perplexed me: “How much is enough?” I had no idea. But I was determined to escape Haight Street.

I schemed for years about purchasing the dream home: any large recently updated Victorian in a gracious San Francisco neighborhood, preferably three stories (one per person) with an expansive view of San Francisco Bay. But the sad truth was that I would never be a high-enough-earning lawyer. I believed in my excellent litigation skills, but, alas, not in my ability to recruit the clients I needed for that high income practicing law. The outcome of the law career sweepstakes was there for me to see. My earnings as an attorney never would get us that home I dreamed about. Not in buoyant San Francisco where property values shot up as fast as my income.

And then, soon after the Seder, Stephanie’s mother told me she had put the problem before Benedict and he had an idea for our dream house purchase. I was moved. Here was Benedict considering my wish, unsolicited by me. This is exactly how John Beresford Tipton, Jr. would have handled it. “And so,” I thought, “this is my ‘Millionaire’ moment. I had followed the Benedict Rule. And now help is coming from the bottomless Benedict fortune.”

Well, not exactly. Our brotherhood moment at the Seder had prompted Benedict to offer his financial brains, not his wallet. He proposed that Stephanie take her inheritance from her mother now, and use that share to expand our money for a house purchase now. It was ingenious, with no divine financial intervention by Benedict. But we would have to marshal all our resources, current and future, to purchase the grand residence I craved. Our actual financial advisor, exasperated by my fixation on a house well beyond our means, finally told me, “You can buy it. But if you do, you will not have a good night’s sleep for the rest of your life.”

Sanity prevailed. I reluctantly backed off the dream house and Benedict’s adventurous financing scheme.

Next, without an advance on Stephanie’s inheritance and without any miraculous million-dollar gift from Benedict, with our own hard-earned dollars, we bought a lovely two-story craftsman house near Golden Gate Park, with an ocean view from the upstairs bedrooms, and, if you count my basement study, one floor per person, all in fine condition, no fixer-upper. We acquired it with steady nerves in a frightful bidding war, at a heart-stopping high price during one of San Francisco’s many real estate booms, and to my amazement it only became more valuable over the following years. That house, where we now live happily, and where I can sleep well, is where I later imagined hanging Woman with Homunculus.

* * *

A new career followed the new house. At 56, I left private law practice to escape soulless litigation, unrelenting pressures, endless hours, business instability, and my maddening inability to break into that elusive high earnings bracket. At the dismal conclusion, private law practice meant not enough money for onerous work I did not believe in.

I surprised myself with unimagined success in my next profession: a court administrator. At 57, starting as a staff attorney in 2001 at the California Administrative Office of the Courts, I quickly climbed to the top, becoming one of the agency’s directors, with large responsibilities for administration of the sprawling California court system. I believed in this work, in our mission to foster a strong justice system for millions of Californians. Building democratic state government, I was true to my civic ideals from the Sixties. This was my well-chosen new path, no detour, after years as a hired-gun litigator. Here I flourished. And, unexpectedly, as I climbed to the top of the agency, I earned more than I had as a litigator. This was one of those extraordinary jobs where I was paid well for doing well.

Benedict became my mentor on how to be a top dog administrator. He respected my job as director doing public service work with the court system. I brought him my top management problems, like how to succeed with my unrelenting boss, how to direct my troops of employees, and how to control my scarce time. He knew nothing about court administration or succeeding in a bureaucracy, but he was shrewd and helpful with difficult advice about people. I affectionately called him my “tor-mentor.”

As a thank you for the mentoring, I treated Benedict to lunch in 2006 after visiting my daughter in college near New York City. When the check came, I took it and paid without fuss, and Benedict thanked me. Just as I had long planned. I felt I had discharged a lingering obligation from the 1980s, at that San Francisco bistro, when Benedict had complained about always footing the bill, and I had realized I must be ready to pay for Benedict. I had settled up, with myself.

A few years later, during the 2007-2008 Great Recession, I heard reports that Benedict was working around the clock to protect his commercial real estate empire. Then came surprising news about Benedict reducing his monthly stipends to people he supported. Supporting others? Yes, it was so, helping others with his fortune. Was Benedict a John Beresford Tipton, Jr. after all? Not quite, since he cut back these charity cases in this time of need, so that everyone sucked it up when Benedict felt pinched. I felt relief that I was not on the Benedict dole.

Benedict weathered the financial storm just fine, to judge from his subsequent purchase of Woman with Homunculus. But at the beginning, with the reports of his difficulties, I inevitably found myself musing, “I guess there will be no million-dollar gift soon.” That wish would not disappear, even as I celebrated my independence from Benedict.

Then I realized, cheerily amidst the crash, “I am a millionaire!” It was not just the result of astronomical San Francisco property values. Stephanie and I had accumulated a small fortune the old-fashioned middle-class way, through two professional incomes, inheritances, careful expenditures, and cautious investments. Of course, a million dollars no longer was the million dollars of the 1950s world of The Millionaire. But this epiphany revealed that I did not need Benedict’s million-dollar gift that never would come.

I still enjoyed any compliment from Benedict, and he inadvertently gave his highest during my years as a court system director. In one of our conversations about my job, he mentioned as an aside, “Odd, you never were interested in finance.”

After all these years, he had just realized that I had the ability for this highest calling in the Benedict universe. I was flattered. I sometimes wondered how I would have done in finance. But I regarded the finance sector, with its millions of dollars in bonuses sloshing around, as best represented in the Rolling Stone cover showing Goldman Sachs as a giant squid sucking the blood out of America. Thank you, Benedict, but law practice was enough of a roundabout route to a satisfying career that paid. No finance detour for me.

* * *

I was mystified by my daughter Julia’s indifference to Benedict. Julia enjoyed Benedict’s hospitality when she was at nearby Vassar College, and I think she saw his guest apartment as a good crash pad while visiting Manhattan. But she was not awed by the penthouse, the art, the fortune, or Benedict’s large living, even when he took her to an elegant art opening and introduced her to other magnate collectors.

Later, when Julia worked for the labor movement, mobilized with Occupy Wall Street, and aided union drives to organize Walmart workers, I received a report that she had lectured Benedict on raising taxes on the 1%. Benedict had a keen interest in Julia. But he rolled his eyes at the sermon, I heard, and Julia responded with another tirade on divesting from the big banks. Benedict later told me that Julia’s rants had prompted him to join a group of wealthy businessmen who advocated a higher tax rate on their carried interest income.

I never had lectured Benedict about the world of hurt and need out there, or the responsibility of the wealthy to help others. But Julia, with her well-grounded sense of what is important, had given him a taste. And Julia had organized him. Go, Julia!

Outside such visits, Julia did not give another thought to Benedict and his wealth. I wondered how she remained impervious. Was it her youth, her lack of experience with the difficulties of poverty or the pleasures of fortune, or her own modest privilege? Was it her commitment to social justice movements? Her temperament? After all, she never had liked difficult people, and Benedict was nothing if not difficult.

I thought it was her view from the millennial generation, with their diminished expectations for jobs, financial success, and upward mobility. Fabulous fortune was within my baby boomer imagination, born in the unlimited possibilities of the postwar boom, where Benedict’s penthouse and art could co-habit with Joe Rapoport struggling to build unions and socialism. But in Julia’s world of millennials, perhaps a more realistic place, Benedict and his tens of millions simply were irrelevant.

* * *

Benedict, still working with his real estate investments at 80, continued to offer advice when it came to my retirement. Terrifying advice.

He told me I first had to pay off my mortgage (with a recent refinance, about 29 years of payments remained), and that I needed retirement income at my employment level (also around 29 more years to build up my state pension). In one discussion, after we reviewed my projected retirement income, he looked at me, puzzled and alarmed, but apparently not wanting to distress me, and he cheerily concluded, “Well, it’s better than a poke in the eye with a stick.”

Tormented again by Benedict, I consulted again with our real financial advisor about my retirement projections. And there was Stephanie with that same insidious question: “How much do I need to earn?” Which meant, what is our standard of living in our retirement? Or, how much is enough?

And now, my employment journey concluding at 67, I finally had some answers:

Pay off the mortgage first? Wait until my retirement income matches my work income? Benedict, get real. No need for that much.

Buy a new house? No, I’m satisfied with ours…well, a new house is unlikely…we already have more than one floor per person and we are close to the ocean...but, wait, let me know about something truly wonderful, with a genuine Bay view…the dream house we can afford.

Buy a new car? Regretfully, yes, one. I hate spending money on cars. But our cars were 10 and 20 years old. We needed something reliable.

How about travel? Manhattan? A Grand Canyon river rafting expedition? Tour Sicily? An Antarctic cruise? Yes, yes, yes, and no. That last adventure was just too expensive.

Otherwise, continue…specialty food shops, clothing boutiques, new electronic devices, theater and dance performances, interesting restaurants, Pilates trainer, biking and hiking gear…no problem…enjoy the consumption.

Help Julia if she does graduate work? Absolutely. No crushing student debt for my daughter.

Stephanie’s retirement? Whenever she’s ready.

Earn supplemental income in retirement? No, I would resume writing popular history, a proven non-paying occupation.

Leave a comfortable inheritance for Julia? Definitely. She’s young and radical. She’s confident and capable. But, like my parents haunted by the Depression, after the Great Recession of 2007-2008 and the COVID-19 pandemic of 2020, the future economy now worries me. I want my daughter to have some financial security in this perilous world.

I finally had figured out how much was enough. We had it.

The outcome was substantially more than what my parents had when my dad died in 1980. On the shoulders of my parents and grandparents, I had climbed into the affluence of the upper middle classes, just as Skokie had promised in the 1950s.

And, thank you detours off the Skokie tracks, which actually were my true route too. It had been an interesting and productive life journey, veering away from my 1950s plan to become a tax attorney. Through my unexpected career as a historian in the Sixties and Seventies, I wrote those books on the Jewish chicken ranchers, my proudest professional accomplishments.

* * *

In 2012, just retired, I learned that Benedict had decided to sell his art collections and penthouse, place proceeds into his charitable foundation, and relocate to Miami. I could not imagine Benedict off the top of Manhattan, with a shrunken retired life along a Florida beach. But next thing he had two luxury condos on Miami Beach, one for guests. He was expanding his longstanding foundation for promoting reading skills of at-risk youth. And soon there was a date for sale of the Expressionist art collection at his dealer’s London gallery.

But wait! That foundation, now to be funded by boxcars of dollars from sale of the art and the penthouse. I had heard about the foundation from Benedict for years. It was the real thing, with success training teachers to teach reading and a commitment to reach children who faced obstacles learning to read. With my background in education and law, tight friendship with Benedict, and sterling character, I’d be a terrific board member. I believed in child literacy. I was excited by the prospect of wisely distributing those millions. And I would enjoy the junkets to New York City for the foundation board meetings.

I telephoned to get myself up on the Benedict radar screen. We had a long discussion about our legacies, his reading foundation and my chicken rancher books.

While we were at it, I could not help wondering about his plans for the other tens of millions of dollars. And, of course, my Millionaire gift…any chance it might be a few words in his estate plan? This wasn’t really breaking the Benedict Rule. Just habit.

But Benedict’s interest in me remained fixed on mentoring, now for my retirement activities. No, he had other plans for the foundation board, and he swatted away my offer. He told me to do ACLU volunteer legal work. He had me pegged, accurately.

I had flagrantly violated the Benedict Rule by seeking that foundation position. So, I would not get it. The same outcome as when I sought nothing. Was there a lesson? Yes, my own decades-old wisdom: the only goody for me in the Benedict world is to ignore those piles of money and enjoy Benedict himself. And to enjoy Benedict, you’d better be following your own passions and earning your own way.

I did internet research on the London sale of Benedict’s Expressionist art collection. The value was publicly reported at one hundred million pounds, at that time one hundred and sixty million dollars. Sales of his other art collections for more tens of millions were yet to come. Staring into my computer, reading the London newspapers, I marveled. I knew this billionaire.

In my online investigation, I came across a curious quarrel: Benedict railing to the British press against new “trophy hunter” multi-billionaire collectors, hedge fund guys acquiring art for investment, inflating prices, using “sharp elbows” to drive out the “connoisseur collectors” like Benedict who acquired for appreciation. Here was Benedict casting himself as the heroic little guy aesthete. He was indignant. Knowing something about Benedict’s own elbows, I was tickled.

Researching Benedict’s London art sale, I encountered an old acquaintance, Woman with Homunculus. There on the internet was the intriguing young woman, strange child still clutching onto her, glancing out to me again, surely disappointed that her next residence would not be my living room wall. And there was an interview with Benedict explaining that he was ending his stewardship, passing on these treasures to the next worthy wealthy collectors. Woman with Homunculus was the piece he most wanted to keep, perhaps “take it to the grave,” but now was the time to “let it all go.”

Before he died in 2016, Benedict had moved on to a new enterprise: oil. Potentially massive! He once explained it to me. Something about locating Texas geological formations with ignored small oil pockets, and “American energy independence.” If the software search program was a break-through, he told me, he could make more money than he had from real estate. What, I wondered, would that look like? Benedict’s life with two billion? Three billion? Benedict was not one to let go.

But I let go…of Benedict the billionaire, that is. Goodbye Woman with Homunculus. I had blazed my own true path, without any gift Expressionist painting hanging in a dream house on a leafy curving street financed by the imagined law career that never quite was.

Goodbye Benedict’s penthouse, at the pinnacle of Manhattan, with those Expressionist masterpieces and all that Tiffany glass. I once had felt at home there, but off they went to the next billionaires.

Goodbye Benedict’s treats to restaurant meals. Those treats were too expensive. When Benedict visited the Bay Area in recent years, I went low-end and took him to neighborhood Asian dives with delicious cheap food, where no one cared who paid. Benedict, a true foodie who loved bargains, was ecstatic. And I was comfortable picking up the tab.

Goodbye to John Beresford Tipton, Jr. and his life-changing million-dollar gift that never arrived. I preferred giving to Benedict: take him on a tour of the stunning northern California coast to my unique Chamokome ranch, no Silverstone, but an overnight stay at a genuine California collective. Rather than more fantasies about the arrival of a million dollars from Benedict, I had actual satisfaction giving Benedict the real gift of my company in a genuine California experience.

I did one other favor for Benedict in recent years, a big one. I helped his granddaughter in San Francisco with some legal matters, and she and I became pals. Benedict was grateful. He even offered to pay for my legal assistance, which I refused. As I had learned from Benedict when I began law practice, you don’t charge for helping family.

I declined another request from Benedict: that I help his foundation by developing contacts with Bay Area educators for dissemination of its innovative reading program for children. Here was the invitation I once sought, and it tempted me again. But no, this was Benedict’s charity project, doing well without me. I was busy with my own writing.

Before Benedict died, I assumed one of his business responsibilities. I helped his sister, Stephanie’s mother, with a shopping center Benedict had arranged for her to purchase. Over the coming years of managing that property, I was not surprised to discover that Benedict had put her into a terrific investment. I also found that Benedict left the legal organization of that property in a mess, a legal clean-up job for me, and I stayed on to run it. Turned out, at the end of my career as a lawyer, rather than me catch Benedict the whale as a client, the whale drew me back into law practice to manage one of his money-making projects, this one for my family. And I actually enjoyed it, particularly when I conferred with Benedict about the business.

And, so finally, goodbye Benedict Rule, with all that not expecting money, not wanting money, and not asking for money. And, yes, finally, goodbye Benedict’s money, money, money, money, money. No problem. I was only one degree of separation from Benedict, but I didn’t need Benedict’s money.

I had learned how much was enough, and I discovered I had it. I had developed my own friendship with Benedict, not his stacks of bills. And I had moved on. Money isn’t everything, not for me, not now.

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Ch. 4 - Joe and Me: Two Generations on the Jewish Left