The 1989 cover of Savvy Woman and an outtake from the photo shoot. Left to right: Blanche Sprague, Donald Trump, Susan Heilbron and Barbara Res. (Photos: George Lange)

Donald Trump grinned out from the cover of Savvy Woman magazine in November of 1989 flanked by three women wearing big shoulder pads, high collars and plenty of kohl eyeliner.

“Trump’s Top Women,” the headline read. And the subhead: “Surprise! Mr. Macho’s Inner Circle Isn’t An All-Boys’ Club.”

Surprise indeed.

For those who see Trump as a paradox and a conundrum — a billionaire Republican who favors taxing the wealthiest, a man who has described himself as both “very pro-choice” and “very simple, pro-life” — add one more contradiction to the list. While he’s spent his whole career saying things that are arguably sexist, like “You wouldn’t have your job if you weren’t beautiful,” and things that are seemingly patronizing, like “I cherish women,” and “I will be phenomenal to the women,” Trump has consistently hired women for positions of real power in his organization and been darned proud of doing so.

As he told George Stephanopoulos on ABC’s “This Week”: “I’ve had such an amazing relationship with women in business. They are amazing executives. They are killers.”

Twenty-six years ago, for instance, when Savvy Woman ran him on the cover, four of the eight people in Trump’s innermost circle were women, including his then wife Ivana, who was not in any of these particular photos but who was running the Plaza Hotel at the time. The others, all executive vice presidents, were: Barbara Res, who was in charge of construction of Trump Tower and then the Plaza; Blanche Sprague, head of project development; and Susan Heilbron, who was Trump’s chief lawyer.

Heilbron did not return repeated requests for an interview, but Res and Sprague both described Trump as a supportive boss who gave them a shot in an industry that was particularly unwelcoming to women.

“When I first started at this, I’d find nasty drawings of myself on the job site, and men would try to intimidate me by peeing on the girders,” says Res of the years right around the time she met Trump.

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Which makes it all the more striking, she says, that he hired her for his signature project, because he liked the way she stood up to the men when he was working for another builder. This was before his bodyguards, his bestselling books, and his comb-over, Res says, back when there were just six people in the entire Trump Organization, back when Trump drove his own limo to Res’ father’s funeral because the chauffeur was off that day. Overnight Res went from earning $25,000 as an assistant supervisor to $55,000 as vice president. She had never run a project before, but “he told me he knew I could” build Trump Tower, she says.

Sprague tells a similar story. She entered the real estate business as a 19-year-old divorced single mother who worked her way up through the sales part of the business, landing on Trump’s radar at a meeting where she more than held her own in a roomful of men. He said something like “I love that mouth, and I have to have it,” before offering her a job at about the same time as Res.

An outtake of Sprague from the Savvy Woman photo shoot and magazine spread. (Photos: George Lange)



Sprague, who is now retired, says that Trump did not hire her because “I am a woman. He just hired who he thought was the best person for the job.”

Res, who now runs her own construction consultancy, is not so sure. There were bragging rights that came with hiring her, she says, and Trump “was quoted lots of places saying he’d hired the first woman to build a big skyscraper.” There were publicity bursts too, like the cover of Savvy Woman, with its very pre-Clarence-Thomas-hearing photos of women executives posing in some fairly unexecutive-like ways.

Sprague particularly cringes at the photos, which, she stresses, represent the times but not the boss. “He didn’t pose those pictures,” she says. Res, however, points out that the idea for the Trump-and-his-women shoot was, at the least, approved by him and, at most, “probably even his idea because he was always looking for ways” to market himself.

Both Res and Sprague agree, however, that whatever Trump’s motivation for bringing them aboard, he treated them equally once they were there — with no sexist diminishment and certainly no added deference.

“If you did the wrong thing, he got as mad at you as he got if you had a mustache,” Sprague says.

Adds Res: “He never even indicated — maybe I should feel badly about this — that I was a woman. It just wasn’t an issue.”

Except, maybe, when it was. Trump’s current habit of commenting on everyone’s looks — calling Rosie O’Donnell “fat” and “extremely unattractive”; questioning whether anyone would vote for Carly Fiorina because of “that face” — is more than familiar to the women who worked for him decades ago.

In Res’ book, “All Alone on the 68th Floor: How One Woman Changed the Face of Construction,” which she self-published in 2013, there are a number of passages like this:

The day the meeting was held, Donald hand picked the secretaries, “girls” in the office, who would receive guests, bring in the sandwiches and coffee, etc. Donald didn’t care what Susan, Blanche or I looked like because we were worth our looks in value, but for greeting visitors Donald wanted the world to think that only attractive people worked for him. As a matter of fact, one day (during protests over Trump’s development near the West Side Highway) Donald was set to take a meeting with a female leader of the opposition over lunch at the Plaza. Although I had other things to do and was not necessary to the subject matter, Trump made me join him so he would not be seen sitting alone at his table with this particularly ugly woman.

This lens was not technically sexist, some who watch him closely say, because he was equally likely to jab at men because of their looks. Michael D’Antonio, author of the just published “Never Enough: Donald Trump and the Pursuit of Success,” describes a balding male executive whom Trump confronted with a suggestion to use Rogaine because, he reportedly said, “going bald is the worst thing you can do.”

“For him it is all about appearance,” D’Antonio says. “You serve him both by your competence and your looks. He wants everyone around him to seem the way he wants to seem — the best-looking, the smartest, the best. Appearances matter more than anything.”

Choosing women for high-profile, untraditional jobs is consistent with this constant awareness of how things look, D’Antonio says. Take one of Trump’s favorite lines back then: “Men are usually better than women, but a good woman is better than 10 men,” something both Res and Sprague report hearing often. Trump took pride in his knack for finding those rare women, and once he chose them, he declared them the best, rarely changing his mind.

“Our team was ‘the greatest.’ I was ‘the greatest.’ He put everyone in two groups, either ‘the greatest’ or ‘a loser,’” Res says. “And then he stuck to his opinion.”

The magazine spread and an outtake of Heilbron from the Savvy Woman photo shoot. (Photos: George Lange)



One high-profile exception was Carolyn Kepcher, whom he plucked from her job running one of his golf courses, made into a TV star as his right-hand woman on the early seasons of “The Apprentice,” and then fired when she began overshadowing him with solo appearances and her own line of books. But most of the time, ironically, the man who made “You’re fired” into a meme is uncomfortable dismissing employees, in part, D’Antonio theorizes, because acknowledging their failure calls into question his initial judgment that they were the best.

And what of Trump’s current inside circle?

It isn’t entirely clear who is in that circle, D’Antonio says. “It’s a kind of mysterious and unconventional structure. If he has a dozen people who interact with him on a daily basis, that’s a lot.”

The most trusted of those is his daughter, Ivanka, who replaced Kepcher at Trump’s side on and off the screen. His longtime executive assistant, Rhona Graff (whose title is senior vice president — assistant to the president), and his publicist, Hope Hicks (whom he “discovered” when she was working for Ivanka’s fashion line and who now helms his campaign PR), are also in his daily orbit. But of the others: “I have met eight or nine, and they are all men,” D’Antonio says.

One of those men, general counsel Michael Cohen, has adamantly insisted otherwise. Irked by constant charges in the press that Trump is a misogynist, he took it upon himself to ask for what he stresses is “not a scientific” tally of the number of women in high-level jobs in the organization. The employees of all Trump’s combined businesses are 57 percent men and 43 percent women, he said in an interview with Yahoo News, but “when it comes to executive positions, there are more females in executive positions at the Trump Organization than males.” (Yahoo News could not independently confirm those numbers.)

Cohen says the women are paid more too.

“He’s not a gender-based leader; he’s a performance-based leader,” Cohen says. “And because so many of the women have been here longer than some of the men, in many instances their salaries are higher.” In the accounting department, he says, “the senior male is in the $70,000 range and the senior female’s salary is slightly greater.” And in his own legal department, he says, “the assistant general counsel makes $25,000 more than her male counterpart.”

On the campaign trail, Trump has expressed more support for equal pay for women than many other Republican candidates, although he has said he wouldn’t want to codify that legally into a “a negative where everybody ends up making the same pay, because that’s not our system.” Where he has offered an opinion on other women’s issues, it is often more liberal than those of his fellow candidates. On the question of funding Planned Parenthood, for instance, he has said, “I would look at some of the good aspects of Planned Parenthood … because I’m sure they do some things properly and good … We have to take care of women.”

One woman with a particularly high profile at the Trump Organization is Sarah Malone, executive vice president of the Trump International Golf Links in Aberdeen, Scotland. She got her start with the organization when Trump plucked her out of nowhere and put her in charge.

About six years ago, Malone, a Cambridge graduate with a degree in fine art from the Glasgow School of Art, was running a small history museum in Aberdeen. She had some local fame, having won a competition to be “the face” of the region, with her photo on billboards and banners to boost tourism.

The local paper had written about how she’d increased the number of visitors to the museum; and in the same issue, there was an article about Trump’s controversial plans for a new golf course in Aberdeen. Reading about himself, Trump noticed the piece on the opposite page about Malone, “and I thought, ‘That’s interesting,’” he told a Scottish website in 2009. “So I called her and I said, ‘Do you know anything about golf?’ She said ‘No.’ So, I said, ‘Good. You’re hired.’”

An outtake of Res from the Savvy Woman photo shoot and magazine spread. (Photos: George Lange)



In the six years since, Malone has overseen the project through planning and construction, opening the golf course in 2012, the hotel in 2014 and the clubhouse this year, all in the face of some local protests against commercialization of the land.

In an email interview, Malone praised her boss, saying, “Unlike many employers, women are given equal status in the business. I report directly to Trump. He is tough, but he’s a great motivator and empowers his team to get results.”

The women who preceded Malone as Trump’s “It Girls” all those years ago are not surprised by her Cinderella story or her loyalty. And they expect that her tenure will be long and her eventual departure fairly amicable because, despite his mercurial public persona, that’s the way the boss does things in private.

“He was the best boss I ever had,” says Sprague, who left the Trump Organization after nearly 20 years and created her own real estate brokerage.

“Yes, he’s a megalomaniac,” says Res (who offers that she plans to vote for Hillary Clinton for president). “And I don’t see how any woman can support him because of the way he talks about women in public. But he wasn’t like that to the people who worked for him, not his top people. Go figure.”