When it opened in 2010, the second-floor lounge at the Trump SoHo New York was decorated with a lavish collection of books bespeaking serious style credentials. Cocktail tables groaned with weighty monographs devoted to leading architects and designers. On the shelves, though, was something more rare: a complete run of Playboy, bound in luxe leather. If Donald Trump has a maestro in matters of taste, it’s surely his fellow teetotaler and sex fan Hugh Hefner, the pajama-clad, Pepsi-swilling progenitor of the lifestyle that so intoxicated boys of The Donald’s generation. Did creased editions of the magazine reside under the young Trump’s military-school mattress, as they did under those of every lad of conventional boomer proclivities? Even more important: Were the most distressed pages the centerfold, or J. Paul Getty’s 1961 column “How I Made My First Billion”?

Trump’s politics are, like Hefner’s “Playboy Philosophy,” an impossible combination of liberalism, hedonism, bloviation, and misogyny. Both men have made world-class contributions to the objectification of women, whether via centerfolds; the Miss Universe, Miss USA, and Miss Teen USA pageants; sleazy remarks; or the slimy prurience of their lecherous gazes. (My daughter is hot! Melania’s a 10!) But Trump does more: He objectifies—brands—everyone. Professional wrestling does for bulked-up guys what beauty pageants do for gals with the proverbial hourglass figure. And what could possibly be more objectifying than his ownership of jocks, whether Herschel Walker and Doug Flutie (who played for Trump’s New Jersey Generals in the short-lived United States Football League) or his erstwhile supporter, the rapist, ear-biting brute Mike Tyson?

Is it simply an inadvertent influence of the countercultural ’60s that his logo is tonsorial and his persona political? Much like Hitler’s mustache, Trump’s helmet of hair is his metonym. I don’t make this comparison lightly: While The Art of the Deal is no Mein Kampf, the media fixation, the facility for propaganda, and the grandiosity make for uncanny parallels. As Hitler (who also wanted to make his beleaguered country great again) put it, “The correct use of propaganda is a true art.” The Donald is even more unabashed: “I have always gotten much more publicity than anybody else.”

Because Trump’s main field of play is real estate, hence architecture, the coincidence of his rise and architecture’s own theoretical and practical fascination with branding is telling. For several decades, the intercourse between modern architecture and the mass media has been lively, and architecture’s own status as a form of media solidified. Playboy’s role here has been much marked. From the first, the magazine was thick with articles and images of modernist buildings and interiors: no end of Eames, Bertoia, Knoll, Wright, Mies, Bucky, Lautner, Safdie, Ant Farm, and many more. Beatriz (now Paul) Preciado points out in the marvelous Pornotopia that “in the late 1950s and ’60s, only one other article…managed to match the popularity of the Playmate nudes: the foldout of the second feature on the Playboy penthouse published in 1959.” Bachelor-pad pictorials were a staple throughout the 1960s, including such gems as an “Airy Eyrie in Malibu,” “A Baronial Bi-level for a Busy Bachelor,” “Exotica in Exurbia,” and “A New Haven Haven.”

Preciado—expanding on the work of Barbara Ehrenreich, Bill Osgerby, and Beatriz Colomina—describes Hefner’s fascination with architectural space both as an enlargement of his claims on hip modernity and as leverage for the co-optation of the domestic for his ideal subject, the heterosexual bachelor playboy. In wresting domesticity (and its designer swag) from suburban imprisonment—­Hefner as a misogynistic inversion of Betty Friedan!—it was crucial that Playboy be dissociated not only from the stereotypical “women’s magazine” like Better Homes and Gardens, but also from any taint of the gay. In the words of Arnold Gingrich, the first editor of Esquire (Playboy’s obvious model), it was crucial to include elements “substantial enough to deodorize the lavender whiff coming from the mere presence of fashion pages.” Per Ehrenreich, “the breasts and bottoms were necessary not just to sell the magazine, but to protect it.” Cheesecake—and those serious articles—guaranteed that Playboy was giving it to you straight, and it placed women in an architectural environment as objects of desire who also unfailingly knew their place. How like the way in which the buffoon Trump (who claims it was he who actually broke the glass ceiling!) deploys the distaff at his events, that inevitable chorus line of beautiful white women—his wife and daughter front and center—both to insulate himself from appearing a chauvinist bachelor and to assert his timeless attraction to, and ability to breed, hotties.

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Like Hefner and Trump, Hitler also worked hard to situate himself in the context of “female” space. In her fascinating book Hitler at Home, Despina Stratigakos recounts the assiduous rebranding of the Führer, from violent agitator to pacific country squire, after his assumption of the chancellorship in 1933. This was frequently accomplished by circulating images of Hitler in sites of domesticity, especially at the Berghof, his Alpine aerie, meticulously decorated by Gerdy Troost (whose dialectical relationship to Leni Riefenstahl—the one focused on signifiers of individuality, the other on those of the mass—is a rife story, still incompletely told). The sobriety and elegance of the structure, as well as its relationship to those mythic mountains—viewed through a picture window the size of a movie screen—served as a corroborating background for an elevated, feelingful Hitler.

This calculated indoor/outdoor contrast marks all three of the specimens before us. Hitler, increasingly confined to a series of bunkers (a word staffers apparently used to describe the Playboy offices), was formed by his doss-house life in Vienna, his failure to get into the Academy of Fine Art, and his years sheltering in the trenches of World War I. Reactively, he sought to order exterior space with grandiose urban schemes and, perhaps most dramatically, with the Nuremberg rallies, where every object and person was situated with unyielding precision. Hefner was more completely interior still, never leaving his bedroom, even traveling inside it in his customized DC-9 with its flying boudoir. Hef’s Los Angeles estate was indoors out, a high-walled Neverland he could traverse in robe and slippers. The germ- and insect-phobic Donald is likewise no outdoorsman: His preferred open-air setting is the golf course, nature in its most tortured, subordinated, and disciplined state.

All three worked overtime to establish and defend their brands in the areas of mass media and retail goods. Disseminated through best-selling books like The Hitler Nobody Knows as well as a rash of souvenir objects, from postcards to dollhouses, the fascist marketing project spiraled out of control, until even Goebbels grew concerned about the proliferation of “tasteless” Nazi-themed merchandise, leading to the passage, in 1933, of the Law for the Protection of National Symbols. As Stratigakos explains, the law was meant to counter such excesses as “Stormtrooper gingerbread, wine bottles and ashtrays ornamented with swastikas, women’s brooches with ‘Heil Hitler’ in imitation diamonds, and alarm clocks that played the Nazi anthem, ‘The Flag on High.’” This was no patch on The Donald, who once filed a lawsuit—partially successful—against two brothers named Jules and Eddie Trump for using their own names for their real-estate company, the Trump Group.

Hitler, Hefner, and Trump—the real rat pack—share a logo fetish (the swastika, the bunny, and the big T are among the most ubiquitous signifiers of their times) and a powerful fascination with building and design. Hefner in the Playboy Mansion, Hitler in the Berghof, and The Donald in his Trump Tower triplex are obsessed with self-­corroboration by decorative context and the dramatic possibilities involved in the public marketing of a “private” lifestyle. Playboy’s masculinization of interiority is nowhere more clearly stated than in Hefner’s editorial in the magazine’s maiden issue: “We don’t mind telling you in advance—we plan on spending most of our time inside. We like our apartment. We enjoy mixing cocktails and an hors d’oeuvre or two, putting a little mood music on the phonograph, and inviting in a female acquaintance for a quiet discussion on Picasso, Nietzsche, jazz, sex.”

The Donald likewise inhabits interiors in lieu of an interior life and shows them off with hyperbolic self-celebration. The tour of the penthouse with its 53 rooms, African-blue-onyx lavatory, ivory friezes, and chandelier “from a castle in Austria” always seems to culminate in a view of Central Park and the skyline outside the glass walls, Trump’s own Alps. Excess is irresistible. Trump himself recalls an early meeting with the architect Der Scutt at his first Manhattan apartment, in which Scutt opined that there was simply too much furniture and proceeded to move half of it into the hall. However, while Trump’s architectural taste isn’t exactly refined, it does have a certain middle-of-the-road precision, as seen in his eye for branded talent and pedigree. Trump’s “portfolio” adumbrates grandiosity without actual risk-taking: The architecture is far more Ralph Lauren than John Galliano—product, not provocation. Indeed, like his father before him (who had Morris Lapidus do a few lively lobbies in his otherwise generic Brooklyn apartment houses), The Donald has fundamentally conservative taste. His buildings break no artistic ground but are accessorized like crazy with shiny signifiers of the sumptuous.

The architects he employs are, if never avant-garde, often from the upper commercial echelon. Adrian Smith—designer of the world’s tallest building, the Burj Khalifa in Dubai—authored Trump’s tower in Chicago. That beloved old Nazi Philip Johnson did the new skin at Columbus Circle; at age 86 (Freudians take note: the same age as Trump’s dad Fred), he was invited to tart up Trump’s Taj, and, at 93, to add his brand to Riverside South. Der Scutt, the designer of Trump Tower (who weirdly changed his name from Don to the German definite article, perhaps in homage to the Donald, although Trump himself, not yet birther in chief, was claiming at the time that the family moniker was Swedish), once worked for Philip Johnson, who also loved all things German. Gilt by association!

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Trump’s breakthrough into the big time was the Grand Hyatt Hotel, designed by Scutt in 1974, an admitted feat of financial legerdemain and, in its transformation from brick opacity to mirror-clad reflectivity, an apposite symbol of the meister’s narcissism, repeated in the global acreage of pure shininess that so embodies Trumpsterstil. There is a method here that joins the self-celebration of an office suite lined with hundreds of magazine-cover pictures of its occupant with a mirror’s ability to enlarge, dazzle, and deceive. In a 1997 profile in The New Yorker, The Donald articulated his aesthetic succinctly: “I have glitzy casinos because people expect it…. Glitz works in Atlantic City…. And in my residential buildings I sometimes use flash, which is a level below glitz.” This capacity to make distinctions that are always exaggerated is surely at the core of the man’s charm, as well as an obvious register of a certain, er, anxiety that Trump is now working through at our expense.

Strikingly, although the small-handed Trump has been involved with some very tall buildings, including the fairly high 58-story Trump Tower, he has had to settle, in the end, for having his name on multiple runners-up, including such second-tier superlatives as the Empire State Building (as part owner), the tallest residential tower in Canada, the tallest completed residential building in the world (a title that will lapse in about 10 minutes), the formerly tallest residential tower in New York, and the tallest building in New Rochelle.

Trump’s one actual go at the world’s tallest building was the Television City project of 1985 on the huge West Side rail-yards site, which featured a proposal for a 150-story, 1,910-foot-high (with spire) shaft as part of a complex that also included seven smaller skyscrapers, each taller than the Trump Tower and designed by Helmut Jahn in his manliest neo-ICBM style. The community and critical pushback was immediate, and Trump soon dumped Jahn for Alexander Cooper, the planner for “traditionalist” Battery Park City—an amiable architect whom Gwenda Blair aptly described as the “anti-Jahn.”

This quick recognition of the limits of his power to manipulate a complex situation led, by turns, to a series of somewhat more “urbane” proposals (adding streets and smaller buildings to the mix, chopping down towers, plazas). Finally, when strong community opposition serendipitously coincided with Trump’s own parlous financial position, an entirely new approach emerged in the form of Riverside South, designed by Alan Ritchie and Costas Kondylis and branded by Philip Johnson. This was a dumbed-down take on a scheme independently commissioned from architect Paul Willen by a consortium of civic groups—proposed in opposition to Trump’s initial grandiosities—many of whom were aghast when Trump himself seized the initiative and became the new plan’s leading exponent.

The now-completed outcome is simultaneously a monument to heightened sensitivity and diminished expectations. The key public benefits in the community scheme were to have been the relocation of the elevated West Side Highway to ground level at the inboard edge of the site and the creation of a major park in the liberated space. Not only have neither of these materialized, but the executed project is architecturally bleak, a monochrome reach of vaguely variegated apartment houses that reproduce the cookie-cutter ethos of his father’s buildings, but with bigger rooms, better finishes, and higher prices. And each, of course, is emblazoned with a giant Trump above its entrance.

As architectural patron, Trump does better with acquired imprimatur, and a number of his holdings—or brandings—have been purchases of distinguished historic properties, such as the Barbizon, the Plaza, 40 Wall Street, and, of course, Mar-a-Lago, which offer old-money cachet to new-money tenants. (Writing about Trump Tower in The Art of the Deal, The Donald declares: “The one market we didn’t go after was old-money New Yorkers, who generally want to live in older buildings anyway.”) His eclectic collection also includes glitzy renovations of well-located dogs (the transformation of the hideous Gulf & Western building into the differently hideous Trump International Hotel, and the sow’s ear to slick purse of the Grand Hyatt) as well as the creation of new structures, including his eponymous tower and the contemporaneous Trump Plaza, not to mention his participation in a plethora of projects around the city and, indeed, the planet under the sign of “the world’s only global luxury real estate super-brand.”

But it isn’t the architecture that makes the man dangerous. Trump and Hefner, his virtual twin, are apostles for “models of masculine consumption,” which Bill Osgerby argues “elaborated a form of sexual politics that was, to a large part, reactionary and exploitative…. The masculine consumer is better seen as part of wider developments in the fabric of American capitalism that saw the rise of a new middle-class faction whose habitus and value system was oriented around an ethos of youthful hedonism and leisure-oriented consumption.” Like Hefner—Kraft durch Freude notwithstanding, Hitler gets a pass here!—Trump is a man whose fortunes derive precisely from hedonism and leisure-oriented consumption (are these the jobs he plans to bring back to America?). And both men rose as vulgarian embodiments of their playboy “philosophies,” preening objects of venal desire. (I am trying to imagine Trump dilating on the will to power to Miss Teen USA over Diet Cokes.)

Trump’s fortunes also derive from his mastery of the con. As he skipped around his creditors during the bankruptcy of his casinos, the courts put him on a personal budget: $450,000 a month, affirming the success of his fuck-you/gimme-gimme attitude toward the system. Trump’s career, like that of his father before him, has been built on playing us for suckers, enjoying house odds, and collecting every available “legal” advantage, from greasing political palms to screwing his shareholders via bankruptcy protection, to an array of tax subsidies, zoning bonuses, and other forms of public largesse. The billionaire tribune of the working class is a welfare queen.

An ironic staple of current cocktail chatter: Was it like this in Berlin in 1932? That fool will never become chancellor. The bombast, the racism, the mustache—impossible. Of course, the comparison goes too far, doesn’t it? Demonizing Muslims is very different from demonizing Jews. And the plan is to keep them out, not throw them out, right? It’s the 11 million Mexicans we actually want to deport, and they’re all criminals. And we’re going to build great things: walls as wide as a country and as long as the autobahn. That sound we hear is the glass ceiling shattering, not Kristallnacht.

Isn’t it?