RFK Jr.'s Relationship History Before Cheryl Hines

There's always been whispers about the notorious Kennedy Curse, that bad luck follows them and those who marry into their family. But the Kennedys' misfortune might have very little to do with an actual curse and everything to do with their seemingly hereditary desire to dance with the devil. RFK Jr. is a prime example. Half of his life's misfortunes could arguably have been prevented had he simply remained faithful to his first wife. But the Kennedy men don't exactly have a good track record when it comes to fidelity, and RFK Jr. is no exception.

As recently as 2024, Kennedy was caught up in a cheating scandal with New York Magazine reporter Olivia Nuzzi, with whom he had apparently been having an affair for about a year, all while still being married to his third wife, Cheryl Hines. The whole sordid affair came to light when Nuzzi fessed up to her fiance, Ryan Lizza, about her relationship with Kennedy. "I was devastated when I learned of Ms. Nuzzi's nearly year-long affair, and I ended our engagement over it," Lizza wrote in court documents (via CNN). He added that Nuzzi told him the relationship with Kennedy was "toxic" and "psychotic." Kennedy denied the affair, with a spokesperson for the politician telling the New York Post, "Mr. Kennedy only met Olivia Nuzzi once in his life for an interview she requested, which yielded a hit piece."

Sources told People Kennedy and Hines were at an impasse in their relationship amid the scandal. "[They] have barely spoken," one source claimed. "She [Hines] is embarrassed because he got caught." What happens next is anyone's guess, but it's worth noting that Kennedy had an extensive relationship history before he tied the knot with Hines in 2014.

RFK Jr.'s first marriage was to Emily Ruth Black in 1982. The two first became acquainted while they were attending law school at the University of Virginia. The couple's wedding day was marked by bad weather (which was, perhaps, if one believes in such things, a bad omen), and it wasn't long before they headed to the Caribbean for their honeymoon.

The two spoke to People (via UPI) at the time, discussing their future plans. They appeared to be the perfect couple who were on the same page when it came to just about everything. They planned on sharing their at-home responsibilities while juggling their respective law careers. "In fact, I'm going to breast-feed our first child," Kennedy quipped during the interview. He also added that he's "the most radical women's lib advocate." Despite this, Black told the outlet she was more than happy to change her last name. Kennedy agreed it was a smart decision. "A name can be helpful in a lot of situations. And Kennedy is better than Black," he said.

The two had big plans for their future family. Since both came from big families (Black had two siblings; Kennedy 10), they wanted to build a dynasty of their own. "We have decided on around five," Black revealed at the time. They never got to five. The couple only had two children, Kick Kennedy and Robert Bobby Kennedy III. Their marriage lasted more than a decade, but in 1994, they called it quits.

RFK Jr.'s marriage to Emily Ruth Black didn't exactly end without a mess, according to Jeremy Oppenheimer's book, "RFK Jr.: Robert F. Kennedy, Jr. and the Dark Side of the Dream." The book, which was released in 2015, spills the tea on plenty of Kennedy family "secrets," and RFK Jr. wasn't spared. Within the scandal-laden pages, Oppenheimer claims Kennedy cheated on Black repeatedly and proposed to his second wife, Mary Richardson, while he was still technically married to Black. The couple got married mere weeks after Kennedy's divorce from his first wife was final, with Richardson already being pregnant with the couple's first child during their nuptials.

Theirs was a turbulent marriage. Kennedy continued his string of affairs, with Richardson later publicly dubbing him a "sexual deviant" and accusing him of "gaslighting" (via Page Six). She claimed Kennedy physically abused her and was a drug addict; he said she abused him as well and told Richardson it was her fault he had been unfaithful several times. Richardson had known the Kennedys most of her life before starting a relationship with RFK Jr., thanks to her friendship with his sister, Kerry Kennedy, which started when the two were 15-year-olds attending Putney together.

Kennedy and Richardson's relationship went down as one of the most troubling Kennedy marriages, with Richardson dying by suicide in 2012, about two years after Kennedy filed for divorce. The couple had four children together.

If you or someone you know is dealing with domestic abuse, you can call the National Domestic Violence Hotline at 1−800−799−7233. You can also find more information, resources, and support at their website. 

It's no secret that RFK Jr. is a serial cheater, but one can't help but raise an eyebrow at the claims that, at one point, he had as many as 43 mistresses. One wonders how he kept up with all of them, and apparently, Kennedy tried to remember who's who by adding some additional details to each contact, like their location and job descriptions. Word has it the controversial politician had a lady in every city, and he didn't always go by his given name. His late wife, Mary Richardson, claimed he often went by Robert Strong when he spent time with female companions on his travels.

Kennedy, who likely knows it would be sheer folly to deny his numerous affairs, hasn't exactly attempted to do so publicly, especially not after some of his old diaries were unearthed. These journals included details about the encounters he had with his staggering number of mistresses. It was Richardson who would discover these journals, where Kennedy referred to his unquenchable desire for extramarital affairs as his "lust demons" (via the New York Post). He even rated all the women he'd been with. Each mistress had a number ranging from one to 10 next to her name. According to Richardson, 10 was code for sex. In one of his entries, Kennedy recorded encounters with three women in one day.

When he was asked about the diaries by a reporter from The Post, Kennedy denied their existence, even though the outlet already had them in its possession. After the deafening silence that initially followed the reporter's question, Kennedy quickly recovered, claiming, "I don't think there is any way you could have a diary or journal of mine from 2001. I don't have any comment on it. I have no diary from 2001."

RFK Jr.'s third wife, Cheryl Hines, was reportedly one of his 43 mistresses, and there are rumors that, in the lead-up to their wedding in 2014, Kennedy was still continuing his philandering ways — this time, with the wife of celebrity plastic surgeon Laurence Kirwan. Kennedy was reportedly in possession of Chelsea Chapman Kirwan's contact information, which, given his track record, was enough cause for suspicion. If reports are to be believed, Kennedy and Kirwan were close since 2012, with the latter's husband apparently being aware of the two's clandestine activities. Records show the two used to call each other about five times a day during August 2012. It's worth noting that Kennedy was in a serious relationship with Hines at the time.

"She didn't say they were having an affair, but she was obviously infatuated. RFK Jr. gave her his book which she was reading, she was very impressed by him," a source told the Daily Mail in 2014 about the nature of Kirwan and Kennedy's relationship. "'Prof Kirwan's away in London a lot of the time, he doesn't have any physical proof — but if it looks like it and sounds like it, the likelihood is they were having an affair. Certainly, Prof Kirwan believes the relationship was inappropriate," they added.

Another source alleged that Kirwan, with her marriage already in shambles, planned to move on with Kennedy once her divorce was final. A source close to Kirwan made it off as utter nonsense, calling the claims "ridiculous."

Despite the media tempest that raged in lieu of their big day regarding RFK Jr.'s alleged affair with Chelsea Chapman Kirwan and claims from a close friend of Kirwan's husband that Kennedy might be subpoenaed in the couple's divorce case, Kennedy and Cheryl Hines still tied the knot in 2014 as planned. Amid some wild internet speculation and questions about how Hines could possibly go through with marrying a man who reportedly cheated on her before they were even married, the New York Post posed the exasperated question: "If Cheryl Hines can take it, why can't we?"

But Cheryl Hines might be done taking it 10 years later. Kennedy's reported affair with political reporter Olivia Nuzzi, which became internet fodder in 2024 as he ran for the presidency as an Independent candidate, might just end their decade-long marriage. Or, at least, that's what one would expect, but sources told Us Weekly Hines is less upset about the alleged affair and more enraged by her husband's newfound affection for President Donald Trump. "RFK Jr.'s] political outspokenness has garnered a lot of polarizing attention. She's worried that it will hinder her work opportunities, given her long career," the source disclosed.

But this doesn't mean Hines is over Kennedy's infidelity. While one could argue she should hardly be surprised, sources told People the whole thing has been "embarrassing" for the long-time actor. "She's been very angry about it. She has a great support team to vent to, though. Everyone's on her side, of course," they said. Apparently, there are whispers of a possible divorce, but Kennedy has apparently appealed to Hines, hat in hand, "begging her not to file," sources claim. Hines, meanwhile, has been spotted out and about sans her wedding ring, which certainly doesn't bode well.