Few people have heard of Lee Hanley — or William Lee Hanley Jr, in full — a businessman and political donor from Greenwich, Connecticut. Yet by the time of his death in 2016, just before Donald Trump’s first election as president, Hanley had played a significant role in the evolution of Right-wing politics over more than three decades. Steve Bannon, the original architect of Trump’s MAGA platform, called him one of the “unsung heroes” of American history. “He had a real love of the hobbits, the deplorables,” Bannon said, “and he put his money where his mouth was.”
In a new book, The Haves and Have-Yachts, a collection of essays written for The New Yorker over the past decade, Evan Osnos describes Hanley as “a bon vivant, with a fondness for salmon-coloured slacks, and a ready checkbook for political ventures”. Hanley inherited, and expanded, a family business in construction supplies and oil. In 1980 he campaigned for Ronald Reagan in Connecticut, developing an approach that, Osnos writes, “uncannily prefigured Trump’s electoral strategy” by assembling “a coalition of conservative elites and the white working class”. Over the next decades he funded numerous organisations and initiatives that promoted a low-tax, small-state conservatism, including publishers, non-profits, and a powerful lobbying firm, Black, Manafort and Stone. (Roger Stone had been one of Reagan’s campaign managers; he would also, along with Paul Manafort, advise Trump.)
Then, after Mitt Romney’s defeat in 2012, Hanley commissioned a pollster to look deeper into the underlying mood in the United States. He was informed that “the level of discontent in this country was beyond anything measurable”. Hanley became convinced that Trump was the only politician capable of channelling this energy in a favourable direction, and set about converting other wealthy donors to the cause. It was a canny investment. Even as Trump gave expression to the anger of Bannon’s “hobbits”, his presidency brought immense material rewards for wealthy Americans, most obviously in the form of tax cuts, deregulation, and financial benefits during the Covid pandemic.
Reflecting on the role of figures like Hanley, Osnos concludes: “The story of Trump’s rise is often told as a hostile takeover. In truth, it is something closer to a joint venture, in which members of America’s elite accepted the terms of Trumpism as the price of power.” That bargain is still paying off today. Trump’s latest budget, which cleared the House of Representatives last month, pledges to entrench and expand the tax cuts passed during his first term. By some estimates, those earning above $500,000 will receive more than a trillion dollars in tax cuts over the next decade, while a similar amount will be cut from government health insurance and food assistance programmes. If we add to this the Trump family’s brazen use of office for self-enrichment, the privileges granted in return for financial contributions, and the political powers given to billionaires such as Elon Musk and David Sacks, then surely all but the most gullible can conclude that America’s regime deserves to be called oligarchy — rule by the wealthy few.
How did the US reach this point? And given the country’s increasingly fragile political and financial position — Trump is adding trillions to an already prolific national debt, even as his policies threaten economic chaos — how sustainable is it? Osnos’ book, subtitled Dispatches on the Ultrarich, provides some important answers to these questions. His starting assumption is that “Trump is a creature of the money-world, and, specifically, of a period of American thinking about greed, fairness, liberty, and dominance”. The essays try, in an almost sociological fashion, to draw back the curtain of this money-world, and “to capture the thinking and behaviour of some of the world’s most powerful people”.
“Surely all but the most gullible can conclude that America’s regime deserves to be called oligarchy — rule by the wealthy few.”
What these forays reveal is that, over the past five decades, a section of America’s elite has increasingly rejected constraints on their ability to accrue wealth, disavowing the notion that their great resources entail any special responsibility towards their fellow citizens. They have embraced a libertarian ethos which casts them simply as private individuals, responsible for their own fate, and entitled to enjoy their riches as they see fit. They have not, however, forgone the prerogative of using their money to shape government and society. The resulting pattern, traced in The Haves and Have-Yachts, has been a “simple arithmetic of compounding — of money making money, of lobbyists layering on new exemptions each decade, of the cultural amnesia that makes ideas about wealth come to seem normal, honourable, inevitable”. In 1978, the richest 0.1% of Americans controlled 7% of the country’s wealth; by 2023, their share was two-and-a-half times greater. Over the same period, the average tax rate of the top 0.01% fell by more than half.
The transformation of the American elite is illustrated by Greenwich, the Connecticut town where Osnos grew up. Known as “the hedge fund capital of the world”, Greenwich is home to a cluster of ultra-rich financiers, who cleave to the privacy of their high-walled estates and their superyachts. But it was not ever thus. The town was once the bastion of an older WASP elite, whose patrician culture included the beliefs that “showing off your money was déclassé”, and that wealth should “justify itself” in both private and public life. Typical of this milieu was Prescott Bush, a congressman in the Fifties and Sixties, and patriarch of the dynasty that would produce two presidents. The “ludicrously aristocratic” Prescott required his sons to wear a jacket and tie at the dinner table, while his grandchildren addressed him as “senator”. His political positions, including a higher minimum wage and taxation to fund investment, reflected a paternalistic sense of duty to the less fortunate.
Greenwich changed in part because its residents, already rich, became much richer, thanks to the post-Eighties boom in financial services. But this coincided with an ideological shift, led by figures like Hanley, away from the Country Club Republicanism of Prescott Bush and towards an outlook focused on personal liberty and suspicion of the state. One decisive moment came in 1980, when Hanley chose not to back local son George H.W. Bush in the Republican primary, working instead to ingratiate Reagan with the genteel denizens of Greenwich. Hanley’s wife even sourced an emergency replacement for the Californian senator’s “ghastly” brown tie.
In Osnos’ telling, this revolt of the elites and the subsequent decades of rising inequality would ultimately force conservatives into their volatile tryst with Trump, as they sacrificed their integrity to surf the wave of discontent which they helped to unleash. The basic insight here is that, while liberal democracies are in theory predicated on equality before the state, in practice they require the wealthy to play along. Once capital becomes sufficiently concentrated, there is always a danger that the richest will rig the system in their favour to the extent that they destroy its legitimacy. Such a moment almost arrived in the Gilded Age of the late 19th and early 20th century, an era of oligarchic power in the US that saw rising class conflict and political violence. It was the fear of revolution, together with the humbling of capital in the Great Depression, that created the opening for Franklin Roosevelt to construct the class compromises of the New Deal. The state expanded massively, and the rich were squeezed: taxes on estates larger than $50 million reached 77% in 1941. In the decades following the Second World War — the heyday of Prescott Bush — rapid economic growth helped reconcile elites to the claims of government.
This contract is now all but dead, its legal basis steadily chipped away. Wall Street discovered “vast new realms of speculation and financial engineering”, but those realms remained to a large extent unregulated. (At the height of the Gilded Age, during the financial crisis of 1907, America’s leading bankers had still assumed personal responsibility for backstopping the system; in 2008, by contrast, taxpayers were forced to take responsibility for them.) Big money moved into tax havens, prosecutions for white-collar crimes declined, and American states began competing to offer the wealthy the most accommodating terms. A proliferation of loopholes around estate taxes have ensured that — contrary to meritocratic justifications for extraordinary wealth — families can keep their fortunes intact from one generation to the next. In 2010, the Supreme Court lifted limits on political donations by individuals, with the effect that “candidates no longer needed large pools of rich supporters; they only needed small pools of ultrarich supporters”.
The horizons of this moneyed class are, of course, much wider than the US itself. After the Cold War, the Pax Americana provided American business with opportunities around the world, while the wealthy had their playgrounds from the French Riviera to Dubai. In Osnos’ portrait of Mark Zuckerberg, the Meta chief almost resembles an imperial administrator, struggling to respond to a genocide being orchestrated through Facebook in faraway Myanmar. And the ultimate symbol of 21st-century wealth is the superyacht, “the most expensive objects our species has ever owned”, an artefact designed to flaunt money but also to enable the purest, most solipsistic enjoyment of it. (The fund manager Edward Lampert named his 288-foot vessel Fountainhead, after the Ayn Rand novel beloved of libertarians and defiant teenagers.)
Osnos’ subjects would doubtless dispute his portrayal of their self-interestedness. Tributes to Lee Hanley, for instance, noted his commitment to employees at his business, and many wealthy Americans devote large sums to philanthropy — though the preference for such personal largesse over tax contributions tells its own story about changing notions of public responsibility. More importantly, by treating Trump as the ultimate expression of oligarchic power, Osnos underplays a salient aspect of oligarchy in the American system: its presence on both sides of the political divide, Republican and Democratic. Wealthy elites wield plenty of influence among Trump’s opponents, as some of Osnos’ own vignettes suggest. In 2017, a raft of eminent liberals aboard the yacht of media executive David Geffen included Barack and Michelle Obama, Bruce Springsteen and Oprah Winfrey. Or consider the Getty family, heirs to mid-century America’s greatest fortune. Gordon Getty has hosted fundraisers for Kamala Harris and Gavin Newsom at his mansion in San Francisco, while the “artist-model” Ivy Love Getty had her wedding officiated by House Speaker Nancy Pelosi in 2021. A number of the Getty clan are now major donors to progressive causes, even as they energetically shield their vast trust from tax. Alexandra S. Getty has suggested that, while taxes are “very important”, the problem is that “if the wrong government is in control, then they all go to stuff I don’t support”.
In other words, America’s super-rich are not united in a single faction. This is not to say that their involvement in politics is balanced: while Forbes reported on the eve of the 2024 election that Harris had more billionaire donors than Trump (83 versus 52), Trump received more funding from billionaires in total thanks to the enormous contributions of Musk and Miriam Adelson. Moreover, an analysis by Americans for Tax Fairness claims that, taking last year’s federal elections together, “over two-thirds (70%) of billionaire-family contributions went in support of GOP candidates and conservative causes”. It also reports that billionaire political spending is now an astonishing 160 times higher than in 2010.
Still, while it may be comforting for New Yorker readers to think otherwise, big money alone cannot explain how Trump won two elections — or how the Democrats lost them. Answering that question would require, among other things, a more rounded picture of America’s class system than Osnos provides. By his own admission, he is giving us “the view from the top”, but this creates the illusion of a society that is straightforwardly divided between the many and the few. In fact, private wealth is just one source of elite status in modern society, albeit the most powerful. There are also managerial, political and cultural elites. These divisions matter, because they are central to the aims and methods of Trump’s wealthy supporters.
Many leading MAGA figures have a particular antipathy to the managerial class that runs corporate America and Washington D.C. Musk has taken a slash-and-burn approach to bureaucracy in his companies and now in the federal government. Kevin Roberts, president of the Heritage Foundation, the leading MAGA think tank, has written of the need to revitalise US capitalism by systematically diminishing the influence of university-educated corporate managers. Another prominent Trump backer, the venture capitalist Marc Andreessen, has touted something called the “iron law of oligarchy”, derived from the political theorist James Burnham. As Andreessen explained, “there’s no actual system of democracy, because you always end up with a small minority in charge of a large majority in basically every society in human history.” He portrays the Trump-supporting oligarchy as a “counter-elite”, whose goal is to save American liberty and economic dynamism from the rule of “expert technocrats” aligned with the Left.
Of course, Andreessen’s own remarks show that there is some role for democracy even in an oligarchic system: he is discussing a presidential election after all. Intra-elite conflicts can be waged by mobilising popular anger at institutions perceived to be hostile or ideologically corrupt. This brings us to the Trumpian riddle that Osnos sets out at the start of his book: “to understand why a voter could revile ‘the elite’ and revere the billionaire scion of a New York real estate fortune”. One reason is simply that Trump and his allies do not belong to the same parts of the elite as the people this voter reviles. Yes, when wealthy businessmen with Harvard or Stanford credentials attack elites, it is usually self-serving and often cynical; but what matters politically is that there is a considerable audience which thinks they have a point.
In truth, more than one of America’s elite groupings have helped to pave the way for the chaos of Trump’s second term. Since the election, many on the Left have acknowledged their own part in making voters feel frustrated and insecure, whether through the condescending tone of cultural institutions or the dysfunction of Democrat-governed cities. It is possible for an irresponsible and exploitative super-rich class to coexist with wasteful and ineffective governments; in fact, this now seems to be the status quo in much of the Western world. Osnos is right, however, to observe that the disillusionment created by elites is now forcing them to embrace unpredictable forms of populism to maintain their power. Trump will surely not be the final iteration of this process.
