An Inside Look at Donald Trump's Women Problem

He's volatile, savvy and, some say, scary. But who is the real Donald Trump? In a series of interviews with dozens of friends, foes, and the Republican presidential candidate himself, a PEOPLE special report examines the truth about the man behind the bluster.

He has called Rosie O'Donnell "a fat pig," Arianna Huffington "unattractive" and noted that Heidi Klum is "no longer a 10."

But if any doubt remained about Donald Trump's focus on women's looks – or his schoolboy eagerness to rate them – the Heidi Cruz incident made things clear.

After an anti-Trump super PAC posted a scantily clad photo of Trump's wife, Melania, he retweeted a meme comparing her to an unflattering shot of Cruz's wife, Heidi. (Cruz fired back: "Donald, real men don't attack women.")

Many who know Trump say this is part of his M.O.

When Real Housewives of Beverly Hills star Brandi Glanville competed on The Celebrity Apprentice, "He told me, 'Brandi, trust me on this, don't ever wear red lipstick ever again,' " she recalls, somewhat embarrassed. "The comment was unsolicited advice and he really needs to work on his delivery, but now every time I wear red lipstick I get people [on social media] claiming I had plastic surgery so maybe 'The Don' was onto something."

Former employee Louise Sunshine told The Washington Post last year how Trump kept in his desk a "fat picture" of her that he pulled out whenever, in her 15-year tenure with him, he didn't like her work. It was, she said, "a reminder that I wasn't perfect."

The fat-shaming was not limited to women, though, says Barbara Res, an engineer and attorney whose time working with Trump on construction projects from 1978 to 1996 is chronicled in her memoir, All Alone on the 68th Floor.

"He's an equal-opportunity insulter. When heavyset people came around sometimes, he would make comments to them like, 'You love your Snickers.' "

For much more of our special report on Donald Trump, pick up this week's issue of PEOPLE, on newsstands Friday

Along with the takedowns, Trump also doles out compliments. "You're beautiful" is a common refrain – he recently used it on a Washington Post staffer after sitting down with the paper's editorial board for a discussion on policy. Later that day, he offered freelance blogger and veteran Alicia Watkins a job on the spot during an event in D.C., saying, "She's got a great look."

Trump himself has long prided his high female employment rates at his companies, and supporters defend his efforts to level the playing field.

When he realized that the LPGA winner's prize of $215,000 at his Trump International Golf Club was far below what a male golf champ would win, he raised it to $1 million, says his friend of 22 years, Robin Bernstein, who characterizes him as a "workaholic deep thinker."

His friend Omarosa Manigault, who starred on Trump's TV competition series, The Apprentice, credits him with financing her idea for a minority version of The Bachelorette and letting her take it to an all-black network. "When it comes to diversity," she insists, "he puts his money where his mouth is."

Increasingly, Trump has been accused of misogyny. His suggestion on Wednesday that abortion should be illegal in the U.S. – and that there should be "some form of punishment" for women who undergo the procedure under the hypothetical ban – was met with widespread outrage.

Nevertheless, Trump maintains that he is a great champion of women. "The media is so after me on women ..." he tweeted on March 26. "Nobody has more respect for women than Donald Trump!"

On the topic of his more unsavory comments about women, he deflects. "I find that women fully get it," he told PEOPLE in September. "They understand me and they understand life and they're very sophisticated, they're very strong and they're great."

• Reporting by SANDRA SOBIERAJ WESTFALL and AILI NAHAS