In a real way, it was failure that drove my father's success—failure to achieve his original goals was the prod that drove continued effort and accomplishment throughout his life.
Just weeks before he died on February 16, my father finished writing his last book. It's a history of the Bonus Army, military veterans who demanded cash payment of benefits promised to them for their service in The World War (the only one at the time, since politicians had yet to air the sequel). They were brutally dispersed by troops and tanks commanded by General Douglas MacArthur, who was honing the skills he'd apply to more deserving targets in the Pacific a little later in his career. I doubt my old man would have been motivated to labor on that book through the complications of the multiple myeloma eating away at him if he'd achieved his life-long goal of a major bestseller and felt comfortable resting on his laurels.
His writing career started with politics; magazine articles, newspaper op-eds, and the books Radical Libertarianism (1970) and It Usually Begins With Ayn Rand (1971) made his name. But politics damn near broke him. He never expected his 1974 run for governor of New York as the Libertarian candidate to end in electoral victory, but he hoped that his candidacy would win enough votes to gain permanent ballot status for the party. He failed in that goal—and in efforts to continue to earn a living amidst the demands of the election. Breaking with the political preoccupations that had driven him for the previous half-decade, he put on a suit and bluffed his way into a meeting with a Merrill Lynch branch manager by implying that he was a potential big-money client. That he had, instead, a big need for money and had bullshitted his way in the door impressed the guy and landed him a job.
His writing career headed off on a similar tangent as he produced investment books (with a sideline in '70s-appropriate futurism, including an imagined reanimation of a cryogenically frozen Walt Disney) over the next few years. Instead of penning tracts about transforming the country and liberating the population, he appealed to an audience seeking to transform portfolios and liberate checkbooks.
And he wrote not just about money, but about people good at accumulating the stuff, like Donald Trump, Rupert Murdoch, Barry Diller, and the Hunt family of Texas. This was a fortunate turn. If disappointment in politics and political writing hadn't spurred him to move on to biographies, his name wouldn't have featured in newspaper stories and television interviews across the country and around the world 30 years after the shady real estate tycoon who threatened him personally and through proxies as he wrote an unauthorized biography of the man moved ever-closer to, and finally into, the White House. Did he have any insights into President Trump? Why, yes, he did.
And honestly, childrearing was not my old man's forte either. I have memories of a… fraught relationship with my father as a child. We escalated to occasionally polishing our knuckles on each other's faces during my teen years. These incidents provided vigorous workouts, and perhaps a moment or two of regret on my father's part that he'd taught me how to fight. They were a bit rough on the family dynamic though. And the furniture.
Such intergenerational conflict is something of a tradition in my family—enough so that I suspect a major reason some of my ancestors came to this country was to put an ocean between themselves and their own immediate forebears.
And, just maybe, I contributed a tense moment or two of my own to those years of conflict.
But the failure of that early father-son relationship actually cleared the way for something better. When we finally put aside the sparring and the cold war that followed, we were both adults. And we started over.
We'd meet for drinks in Manhattan after work, as much friends as father and son, to shoot the shit and bust each other's chops. I introduced him to Jello shots and the Pogues. He asked me what I was doing with all of that money I was supposedly making in those Bright Lights, Big City days.
Well, Jello shots and concert tickets didn't pay for themselves, did they?
He had not, at that time, yet reconciled himself to the idea of making a living as anything other than an author. Even the lucrative brokerage business was supposed to be a stepping stone until the books he wrote sold enough copies to constitute the entire payday.
That dream… well… failed.
But as he made his peace with that failure—and I won't pretend it was an easy process—he entered what he himself later admitted was the most rewarding period of his life. He and my mother resettled in Maryland. He landed a financial writing job at T. Rowe Price that suited his temperament and gave him time to produce some of his best work. He wrote more biographies, including a treatment of Alan Greenspan that brought him back in contact with the Objectivism that had launched his interest in libertarian ideas.
The Greenspan book wasn't the only time his continuing interest in individualism and personal liberty resurfaced in seemingly unrelated projects. Inside the Underground Economy (1982) flipped the bird to regulators and the IRS in the guise of an investment book. Gallo Be Thy Name (2009) examined how the famous wine-making family found opportunity in a Prohibition era that was supposed to put it out of business. And The Roughest Riders (2015) explored the African-American soldiers who saved Teddy Roosevelt's bacon at San Juan Hill and whose hard-won achievements the future authoritarian blow-hard president claimed as his own.
How could these ideas not recur again and again to the grandson of a speakeasy operator? Many of the relatives with whom he'd grown up specialized in making sure that whatever goods and services the powers-that-be had their panties in a bunch over this decade remained available (and profitable), even if not legal. He'd repeatedly seen control freaks' dreams fail and fuel their opponents' success.
During these years my father and I would spend a lot of time on our patios, at his home in Maryland or mine in Arizona, sipping whiskey, smoking cigars, and solving the world's problems—or, at least, savaging the people we held responsible for them. On his last visit to my home, for Thanksgiving in 2016, we continued our tradition, not knowing it was for the last time.
At the end of the evening, when he tried to get up, he couldn't quite make it and began a slow-motion face-plant. The cancer rotting his innards had stolen away a little more of his capacity for good booze than he'd estimated. That capacity was a moving target, and he'd guessed wrong.
So I threw his arm over my shoulder and lifted him off the outdoor sofa. We walked into the house, both of us laughing at the situation like two buddies exiting after one drink too many from a favorite bar.
In the end, the evening, like his life, was a success.