Donald Trump arrives at a campaign rally, 5 October 2016, in Las Vegas. John Locher/AP/Press Association Images. All rights reserved.On 16 September, Donald Trump surreally began his non-apology for questioning president Obama’s country of birth with a signature Trumpian sales pitch for his new Washington, DC hotel. This go-to mode, the perpetual booster for brand Trump, is well known to anyone who has watched reality TV over the past decade.

Yet, the brand he has created – the brashly successful real estate mogul, who flirts with nativism, and sings the gospel of success – is not his own. It has a much longer and distinctly American legacy rooted, ironically, not in fear but a bullish optimism about the future. It is a form of boosterism for technology, progress, and the free market. No one practices it as thoroughly and pridefully as real estate developers.

Real estate investment has always had a special place in American politics due to the country’s history of westward expansion outward, closely followed by urban development upward. Cities like Chicago, which changed their economic engine from stockyards to skyscrapers within the decade of the 1890s, embody the dual American narratives of cowboy self-reliance and business acumen. Those who made a fortune in real estate, such as John Jacob Astor, who parlayed a fur trading empire into becoming the most important developer in late nineteenth-century New York, are praised not just as being in the right place at the right time but as visionaries who understood fundamental shifts in the modernising US economy.

Today, real estate developers are even more important in the United States economy as manufacturing limps along on life support, global finance makes international property development simpler, and millenials eschew their parents’ suburban dream for urban lofts. Despite Trump’s narrative of racial danger and violence in cities, most American cities are safer than they were 20 years ago and more people want to live in them. Cities like New York may have more buildings under construction by faceless conglomerates than ever but the caricature of the top-hatted monopoly man with a bag of cash – embodied in figures like Trump, William Zeckendorf, Larry Silverstein, and Bruce Ratner – is a powerful cultural symbol of prosperity, gumption, and American ingenuity. Trump has successfully used the widespread familiarity with this figure – at once hero and trickster – to market his candidacy to the American people as the dealmaker-in-chief.

One of the first explorations of this persona was in Sinclair Lewis’s classic 1922 novel that satirizes a relentlessly peppy and go-getting real estate broker, speculator, and developer named George F. Babbitt. Babbitt, based in the left-leaning social realism school of early twentieth-century literature, was a sensation for the way that it explored the psychology of a successful businessman in the booming fictional city of Zenith (thought by many to be Duluth, Minnesota).

Unlike so many American stories that came before it, the book is devoid of Horatio Alger rags-to-riches allegorising. Instead, it is a psychological inspection of a man who grandiosely seeks to emphasise his self-importance and personal capacity at every turn while running headlong from his deep-seated suspicion that he is a fraud. By going back to Babbitt, we can better understand not just Trump’s profession, but the ideology it is based on and the language of glitz and bravado it has provided to successive generations of American developers.

Supporters cheer Trump at a campaign rally, 4 October 2016. Ross D. Franklin/AP/Press Association Images. All rights reserved.Babbitt is a chubby, mid-forties, cigar-chomping, back-slapping, deal-maker. He exults Rotarian civic virtue while making backroom deals and cheating on his wife. Unlike Trump, he is obsessively optimistic about Zenith, about America’s future, and on just about every other issue. Yet, behind his jovial demeanour and motor-mouthed collegial good ol’ boy argot, there is a dark and empty interior.

Lewis explores this inner deadness through Babbitt’s uniquely American projection of optimism. The belief in a better future is Babbitt’s perpetual psychic state: present in every daily interaction. It is also an outgrowth of the booming 1920s business environment of frenzied money-making. In prosperous Zenith, real estate men like Babbitt hope to cut fast deals, build bigger and higher, and to make free enterprise into a gospel, despite considerable evidence that many were left out of the system.

In the first chapter, as Babbitt comes down to his morning breakfast, Lewis observes: “He beheld the tower as a temple spire of the religion of business: a faith passionate, exulted, surpassing common men.” Babbitt’s America is infused with this optimism but also latent fear: socialist ideas among disenfranchised workers were on the rise and America’s success in World War I brought a new global role that was both an honour and a burden. In Trump’s America, there is little optimism but the enemies are also ‘subversive’ foreigners in our midst and America’s role in the world is not as a unique superpower but as a has-been that is constantly getting “ripped off” by other countries.

Babbitt is replete with 1920s banter that is distinctly masculine, jovial, and seems like it was bred in the smoky tapestried rooms of businessmen’s private clubs. Indeed, much of the book takes place in Babbitt’s Athletic Club where he guffaws with other salesmen and lunches on mutton. Unlike Trump, there is a middle-classness to Babbitt’s world in which he is presented as a perpetual striver, originally from a town outside of Zenith where his father owned a general store.

Yet, despite Trump’s copious self-gilding over the years, it bears note that he is something of an upstart whose family made their millions in Queens, not Manhattan. Like Babbitt, Trump’s father made a fortune from building new ‘streetcar’ suburbs, often using government money to pay for infrastructure while reaping profits from homes that flatly denied black renters. Given this in-town but not ‘downtown’ pedigree, Trump styles himself as someone who has made it but is not a blue blood. With this positioning he carries two kinds of class resentment: that of the wealthy who dislike ‘losers’ who can’t make it, but also that of the nouveau riche who are excluded from the aristocratic inner-circle. Babbitt, likewise is not invited to the best parties but makes up for it by fixating on new cars and buying expensive cigar lighters to thrust at any potential client patient enough to hear-out his philosophy on better business.

Babbitt is also a comical moralizer in the age of prohibition when self-satisfied righteousness was in no short supply in cities. He despises bad types who hang around juke joints but he salivates at the mere mention of an illicit drink. He dislikes bohemians but, when a set of them takes him in for a time, he delights in their company – especially assignations with women who are not his wife. Babbitt reflexively despises unions and keeps company with arch-conservatives attempting to free Zenith of organized labour. Yet, he also benefits from the help of a sketchy cabal called the ‘Traction Group’ who secretly buy land near expanding highways and streetcar lines in order to sell it off at bonanza profits – a practice that uses public infrastructure and tax incentives for private profit and which has become the norm for major developers like Trump. The one group that Babbitt cannot understand, and has no time for, are intellectuals: even, sometimes, his dear friend Paul Riesling who is prone to poetic introspection and the desire to stop and consider the changing urban world in the mad dash of the 1920s boom economy. Like Trump, Babbitt is deathly afraid of an interior life that is contemplative and questioning: meditating on the world’s problems too long – without forming a distinct opinion – is a sign of weakness.

Trump speaks during a campaign rally, 5 October 2016, in Reno, Nev. AP Photo/ Evan Vucci. All rights reserved.Babbitt also has a melancholy element of a man torn between two worlds: the staid but friendly clubs for businessmen and the more exciting draw of flappers and speakeasies. Babbitt even briefly decides to buck Zenith’s business elite by defending a college acquaintance and left wing lawyer, named Seneca Doane, who advocates for union causes and the right to strike. While he is quickly brought back into line because of his own sense of conformity and his own material interests, he both defends Seneca Doane and denounces him with the equal fervour of someone who does not know quite what they believe but, whatever they decide upon, shouts it out gustily. Like Trump, Babbitt vacillates between seeking to expose the city of Zenith’s power network while yearning to win their favour and become their leader (he settles on the latter, like the Donald). In short, he has deeply held positions that are eminently changeable.

As many scholars have pointed out, in the near century since Babbitt was originally published, his character has become a perfect example of a man searching for a new kind of masculinity when work and gender were in flux. Unlike his father, who ran a grocery store, the only physical labour he performs is driving clients to examine properties or glad-handing potential business partners at conferences. He is balding and bespectacled: constantly jamming himself into a too-small smoking jacket. His work, devoid of physical labour, is both emasculating and empowering. He has the good fortune to see a new city take shape, to post his firm’s name on newspaper ads and placards, and to get in on the great push from agrarian to urban society. He also sees this new city as a man’s world in which his wife is little more than a matronly bore who keeps his shoes in order and pesters him about his social advancement. The new urban women – represented by flappers who smoke cigarettes and drink gin – are both enticing and unnerving because they present a new form of sexuality coupled with growing independence from families, long term relationships, and the conservative values of stalwarts like Babbitt.

One thing that seems to have changed in the era since Babbitt is the decorum of the aspiring moguls who seek to reshape cities. While Babbitt dislikes immigrants, he also argues to his conservative friends – who equate immigrants with socialists – that everyone is from somewhere else in the United States: a far cry from the presidential hopeful who made his name in politics by calling undocumented Latinos criminals, drug smugglers, and rapists. Babbitt swears but only a stream of ‘daw gawns’ producing comically polite and impersonal expressions of frustration and anger, despite the reader’s suspicion that he might like to get a bit more unbounded and spiteful in his expletives. In short, he is constrained by a civic code of courtesy that was well understood and broadly agreed upon in the 1920s. While the real estate business has not changed much since the days of Babbitt, this sense of congeniality and self–control within public life seems truly antiquated.

Trump seems to have garnered much of his success by importing celebrity from the well-liked realm of business mogul success to the loathed sphere of American politics. Despite the suspicion that he has paid no taxes, he has been championed as the candidate of the forgotten white working class. The US public seems to appreciate someone who lets middle class citizens pick up the bill while writing off real estate losses. Babbitt also prospered from cronyism and no-bid contracts, but while feeling guilty for it. Sinclair Lewis’s story ends in the 1920s but it would be interesting to imagine Babbitt’s character facing the market crash of 1929 when America’s appetite for risk and admiration for speculation vanished. The electorate seems to be hungry for risk again, hoping that candidate Trump can broker a deal in which the US emerges as an unabashed superpower with all the swagger of a New York real estate tycoon.