Story highlights

Trump's circle of advisers have their own history

Their backgrounds come into play as Trump raises Bill Clinton's infidelities

CNN  — 

Days after patting himself on the back for not invoking them on a debate stage, Donald Trump and his campaign are attempting to use Bill Clinton’s sex scandals to cast a shadow on Hillary Clinton.

For any candidate trailing by around 20 points with women in most national polling, this plan of action might seem, at best, curiously wrongheaded. But Trump is a special case – the twice-divorced nominee, who carried on a long affair that disintegrated his first marriage in a howling tabloid spectacle, is uniquely unsuited to finger-wagging.

Still, the irony does not seem to have resonated with his campaign brain trust. On Wednesday, they put out talking points encouraging surrogates to chat about Monica Lewinsky, Gennifer Flowers and Paula Jones. A day earlier, Trump (who is overweight himself) hit back at claims he’d body-shamed a former Miss Universe by noting to Fox News that “she gained a massive amount of weight.”

Odd, but not surprising. Especially when you consider the rogues gallery of advisers Trump has drafted in over the past few months – a pasty collection of older males, mostly media executives and politicians, with a long rap sheet of marital infidelities, sex scandals and worse.

Trump allies will be quick to point out that, even as the candidate is again beset by sexism charges, two of his most influential aides are women. Kellyanne Conway was brought on to manage the campaign this summer and daughter Ivanka, alongside husband Jared Kushner, is widely reported to be one of the few people that truly has his ear.

But the broader campaign firmament is less diverse. Here’s a look at the Trump boys’ club and its unsettling record:

Steve Bannon – allegedly attacked wife

Steve Bannon

Bannon’s precise role on the campaign is still a bit of a mystery. He was hired as the campaign CEO during a shake-up in mid-August, taking leave from his top post at the right-wing Breitbart News operation, to steady what was then a rapidly sinking ship.

His first week in charge ended with word that that newly-appointed boss had, in 1996, faced charges of misdemeanor domestic violence, battery, and dissuading a witness following an incident involving his then-wife.

The charges were eventually dropped, but a police report from the time offers details of the woman’s injuries, including mentions of red marks on her wrist and neck.

A few days later, another story – also involving his ex-wife – surfaced that Bannon, after their divorce, had objected to a potential school for their daughters because, as she put it in court documents, he “didn’t want the girls going to school with Jews.”

Roger Ailes – allegedly harassed numerous women

roger ailes

Trump and Ailes spoke frequently during the early stages of the race, but it wasn’t until the longtime Fox News chief was ousted amid a sexual harassment scandal that he emerged as a more influential voice in the campaign, according to some reports, including providing debate advice.

Multiple women have now come forward, some with lawsuits, alleging sexual misconduct – a number of them in harrowing first-person accounts provided to New York Magazine and other outlets. Ailes has denied the harassment allegations against him, but earlier this month, 21st Century Fox reached a $20 million settlement with former anchor Gretchen Carlson and agreed to a “handful” of other deals with women whose identities were not revealed.

Ailes’ role going forward is a bit of a mystery, but his presence certainly casts a shadow on any effort by the campaign to make inroads with skeptical women.

Ditto for another informal adviser, Roger Stone, who has been working to undermine and insult Clinton for years. In 2008, he created a so-called 527 group whose initials spelled out a crude term for a part of the female anatomy.

Newt Gingrich – cheated on two wives

Former Speaker of the US House of Representatives Newt Gingrich arrives to speak on the third day of the Republican National Convention in Cleveland, Ohio, on July 20, 2016.

Gingrich on Wednesday night jumped on Trump’s bandwagon, offering his assessment of the Alicia Machado Miss Universe controversy to a gathering of Log Cabin Republicans in Washington.

“You’re not supposed to gain 60 pounds during the year that you’re Miss Universe,” said the former House speaker, who has no known experience in or around beauty pageants.

Like Trump, Bannon, Ailes and former New York Mayor Rudy Giuliani, Gingrich has been married multiple times. He has admitted to cheating on his first and second wives – and that he was engaged in an affair while leading impeachment proceedings against then-President Bill Clinton.

Rudy Giuliani – also on his third marriage

Former New York City Mayor Rudy Giuliani introduces Republican presidential candidate Donald Trump during a campaign event at Trask Coliseum on August 9, 2016 in Wilmington, North Carolina.

Giuliani, currently on his third marriage, ripped Hillary Clinton on Monday night for staying with her husband despite his multiple affairs.

“She didn’t just stand by (Bill Clinton), she attacked Monica Lewinsky, and after being married to Bill Clinton for 20 years, if you didn’t know the moment Monica Lewinsky said Bill Clinton violated her and was telling the truth – then you’re too stupid to be president,” he told a reporter from Elite Daily after the debate.

Giuliani’s second marriage, to Donna Hanover, came to a very public and nasty end back in 2001, as the still-married mayor stepped out publicly with girlfriend Judith Nathan – often bringing her to the mayor’s residence at Gracie Mansion. When Hanover protested, Giuliani lawyer Raoul Felder told reporters his client’s wife was “howling like a stuck pig” in her request to ban Nathan from the home.

Michael Cohen – said men can’t rape their wives

Billionaire Donald Trump and his wife Ivana arrive December 4, 1989 at a social engagement in New York.
Donald Trump adviser: 'You cannot rape your spouse'
03:25 - Source: CNN

Marital rape has been illegal in all 50 states for more than two decades, but Cohen, special counsel to Trump and an executive vice president at The Trump Organization, insisted in an interview with the Daily Beast last year that “you cannot rape your spouse.”

The comment came in response to a question about allegations, made in a deposition during their divorce proceedings and revealed in a 1993 book, that Trump had raped his first wife, Ivana, in 1989. Trump has denied it and Ivana subsequently backed off the claim, saying she felt “violated” but did not want her words taken “in a literal or criminal sense.”

Trump distanced himself from Cohen’s remark and the campaign said he was not affiliated with the political operation, despite his having made repeated media appearances as a surrogate. (You might remember a more recent appearance on CNN, when he stubbornly disputed the existence of polls.)

Chris Christie – Truth-teller?

In the aftermath of Trump’s Monday night debate meltdown, campaign advisers have discussed offering Christie a more prominent role in the preparations ahead of the second debate on Sunday October 9.

The New Jersey governor has been one of the few close aides to offer Trump what a source described as a “brutally honest” assessment of his performance in New York.

Christie is already doing double duty as the chairman of Trump’s transition team – triple duty if you include fending off accusations that he misled the public about his knowledge of the Bridgegate scandal.