Bill Clinton's Shadiest Moments

Bill Clinton is that "once in a generation political natural," writes the New York Times. The former governor of Arkansas went from national novice to household name when he upset incumbent George H.W. Bush in 1992. He was only 46 at the time, which makes him practically a toddler compared to many of the equally teetering septuagenarians who would both precede and follow him.

Clinton would win again in 1996, beating 73-year-old establishment Republican Bob Dole, in a landslide. Presiding over the booming economy of the '90s was a wind at his back. The saxophone playing political savant needed all the help he could get.

Sex scandal after icky sex scandal completely engulfed his administration. The accusations were numerous and threatened to upend Clinton's presidency before it even began. Many alleged skeletons from his days in Arkansas, and after, began tumbling into the hands of the national press. Clinton would be caught in lies trying to evade a ferocious new media no longer willing to let the private life of presidents remain that — private. The litany of accusations and lawsuits culminated in 1998 when he was impeached over an affair with a young White House intern. And yet, Clinton survived it all. He remains a popular figure to this day. His ability to connect with Americans, his charm, and his obviously deep intellect somehow carried him through. But the paper trail on "Slick Willy" is long. These are Bill Clinton's shadiest moments.

Monica Lewinsky was just 21 years old when she got an unpaid post-college internship in Bill Clinton's White House — landing the gig by way of a family connection, according to Time. The sexual relationship between Lewinsky and Clinton began almost immediately and eventually included oral sex in the oval office, according to Special Prosecutor's Ken Starr's Starr Report, via The Washington Post. The affair nearly topped Clinton's entirely.

Lewinsky initially denied the relationship, in a 1998 affidavit, after she was subpoenaed in a separate sexual harassment claim involving Clinton. However, she had been privately pouring out her heartbreak about the affair to a backstabbing confidante in the White House, named Linda Tripp. Tripp, it turns out, was wired by the FBI and surreptitiously recorded Lewinsky's rueful confessions as a part of Starr's efforts to find dirt on Clinton. And find it he did. 

Reports about cigars and stained garments soon hit the press. Clinton wanted to fight. He went on TV and uttered an instantly infamous phrase: "I did not have sexual relations with that woman, Monica Lewinsky." The scandal, however, snowballed, and Clinton finally came clean (via CNN), "Indeed, I did have a relationship with Miss Lewinsky that was not appropriate. In fact, it was wrong. It constituted a critical lapse in judgment and a personal failure on my part for which I am solely and completely responsible." Years later Clinton would chalk the affair to, "managing my anxieties," in the Hulu documentary Hillary, via The New York Times.

Whitewater was perhaps the other defining scandal of Bill Clinton's presidency. Not much really came of it, but, superficially, it does kinda sound like Watergate — water is right in there. It began in 1978 when then-Attorney General Bill Clinton and wife Hillary Clinton bought 220 acres of land in the Ozark mountains of Arkansas for just over $200,000, intent on developing the property into vacation homes under the Whitewater Development Corp, according to The Washington Post.

Clinton was later accused in court of pressuring a lending company to make a fraudulent $300,000 loan to the wife of his business partner, Susan McDougal. (Clinton denied doing so.) Susan was eventually sent to prison for illegally obtaining the loan, but refused to cooperate or implicate Clinton. Clinton's partner in the deal James McDougal was sentenced to three years in prison in 1998 on 18 charges of fraud and conspiracy. Kenneth Starr offered a shortened sentence to help him nail Clinton, but James died just months before his release in 1998.

Starr spent four years and $30 million investigating the minor deal in which the Clintons reportedly lost money — about $40,000. Starr gave up in 1998 without drafting an impeachment referral on this charge "because the evidence was insufficient," according to The Washington Post. Some shenanigans with campaign funds and a real estate document drafted by Hillary to "deceive" federal regulators had been found. But overall, the investigation was much bigger than the alleged crime.

If White House counsel/Bill Clinton's childhood friend Vincent Foster had died today, he'd be trending via Reddit's R/conspiracy sub. As it goes, Foster, who was handling delinquent Whitewater tax documents, was discovered shot dead in a Washington, D.C. park in 1993. Local police ruled the death a suicide. Suspiciously though, the White House didn't allow federal investigators into Foster's office, according to The Washington Post. White house aides went in first, "giving rise to speculation that files were removed."

Whitewater investigators found this suspicious too. Present-day Supreme Court Justice Brett Kavanaugh, then a subordinate to Ken Starr, wrote (via The Washington Post), "We are currently investigating Vincent Foster's death to determine, among other things, whether he was murdered in violation of federal criminal law." Kavanaugh wanted to push the White House probe further: "It necessarily follows that we must have the authority to fully investigate Foster's death." Kavanaugh later had a change of heart. In 2009, he wrote for the Minnesota Law Review that impeachment investigations"take the President's focus away from his or her responsibilities to the people."

No suicide note was found, but a missive in Foster's hand, turned up later by White House staff, seemed to speak of his disillusionment. It read, "Here ruining people is considered sport." Starr would eventually conclude Foster's death was indeed suicide. Multiple independent investigations say a depressed Foster put a gun in his mouth and pulled the trigger — gun powder residue on his hand telling the tale.

If you or someone you know is having suicidal thoughts, please call the National Suicide Prevention Lifeline at 1-800-273-TALK (8255) or text HOME to the Crisis Text Line at 741741

Paula Jones' allegations against Bill Clinton would eventually fold into the much bigger Monica Lewinsky scandal. It was a deposition for Jones' lawsuit against Clinton where the president denied, under oath, his dalliance with his White House intern. This bit of perjury largely became the basis for his impeachment. But Jones has her own story.

In 1991, Jones was working for the State of Arkansas' Industrial Development Commission. She found herself at a convention with Governor Clinton where he persuaded her to come up to his hotel suite. According to The Washington Post, Jones claimed, "Mr. Clinton then unexpectedly reached over to me, took my hand, and pulled me toward him, so that our bodies were close to each other. She said Clinton put his hand on her thigh and tried to kiss her neck. Jones retreated. She alleged that's when Clinton pulled down his pants, exposed himself, and told Jones to "kiss it." 

Jones alleged that when she refused, Clinton said, "You are smart. Let's keep this between ourselves." Jones didn't keep quiet. She sued and eventually settled for $850,000. According to The Washington Post, Clinton's team called the allegations "baseless," but settled to move on. Witnesses were divided on Jones' account but she claimed she had physical proof: a description of Clinton's genitalia, allegedly as crooked as the man. However, Clinton's lawyers got three doctors to say Slick Willy was hung straight. Lewinsky later backed up this account of his package for a grand jury, according to Slate. 

Juanita Broaddrick didn't tell anyone what Bill Clinton allegedly did to her for 21 years. She says she didn't think anyone would believe her. She even denied it under oath, according to BuzzFeed News. But in the waning years of the Clinton presidency, she went on Dateline NBC and told her story for the world.

Broaddrick was a volunteer on Clinton's first Gubernatorial campaign in 1978, when she says she found herself alone in a Little Rock hotel room with the future president. "[Clinton] turned me around and started kissing me, and that was a real shock," she alleged. "I first pushed him away. I just told him 'no' ... He tries to kiss me. He starts biting on my lip ... And then he forces me down on the bed. I just was very frightened. I tried to get away from him. I told him 'no' ... He wouldn't listen to me."

Clinton refused comment on the allegations in a press conference that followed and left the denial to his attorney, according to The Washington Post. The story didn't rock the White House like the Lewinsky scandal, partly because of media skepticism of Broaddrick. That may have since changed. "I thought Juanita Broaddrick wasn't credible. I was wrong," is the headline in The Washington Post in 2018. The New York Times opinion page concurs, with the succinct tag, "I believe Juanita." Broaddrick also alleged Hillary Clinton threatened her, and helped her husband cover up the crime. When Vox reached out to Hillary's campaign about the allegation in 2016, they did not reply.

Bill Clinton, you might be realizing, did not fully conform to his marriage vows. He may therefore be familiar with the general structure of an apology to wife Hillary Clinton, whom he wed in 1975. But only one of his alleged dalliances made the apology for him.

"I had sex with Bill Clinton, but the important part to me is that I was never pressured. We had an intimate evening," 1982 Miss America Elizabeth Ward Gracen told the New York Daily News in 1998. "Nothing was ever forced. It was completely consensual." Consensual, but regrettable apparently. "What I did was wrong, and I feel very, very bad about it now. My behavior was inappropriate — that's just the bottom line," Gracen further said (via The Washington Post).

Gracen was initially subpoenaed in the labyrinthine Paula Jones case when a friend alleged Clinton raped Gracen in the back of a limo in 1982. "That never happened. It's completely false," Gracen said (via South Coast Today). "I never told her that Bill Clinton pressured me or harassed me. I don't know why she said that. It baffles me." Gracen said she did meet Clinton in that limo, but they hooked up later in a hotel room. Clinton allegedly wanted another go, but Gracen wasn't down. She simply wanted to clear the record. "The lies gain credibility every day that I don't address them." Gracen said. "This is something I don't want to talk about at all. It's no one's business."

You are the company you keep, according to everyone's mom. Bill Clinton would've been wise to imbibe this lesson.

In 2008, illusive billionaire sex criminal Jeffrey Epstein pleaded guilty to soliciting an underage girl for prostitution, according to The Wall Street Journal. This is of course a euphemism, as a minor cannot consent to "prostitution." Regardless, Epstein mysteriously avoided any serious consequences and re-entered public life 13 months later where he was once again an influential power broker in Democratic politics, and a circuitous donor to the Clinton Foundation, according to The Daily Beast. That ended in 2019 when Epstein died in jail under murky circumstances, by apparent suicide, after the full spectrum of his global sex trafficking operation came to public view.

Clinton has denied knowing about Epstein's crimes. However, he did go on Epstein's private plane, according to The New York Times. This jet is the now infamous "Lolita Express." It operated as a kind of shuttle to Epstein's private island, where he allegedly committed many of his crimes against underage girls. Clinton was photographed getting a back massage from one of Epstein's accusers, Chauntae Davies, in images obtained by the Daily Mail. Davies says Clinton was a "perfect gentlemen," but the former POTUS may have taken 15 different trips to the infamous island, according to fight records obtained by Gawker, or even as many as 26, reports Fox News.

If you or someone you know is having suicidal thoughts, please call the National Suicide Prevention Lifeline at 1-800-273-TALK (8255) or text HOME to the Crisis Text Line at 741741

Leslie Millwee was a local TV reporter in Arkansas in the 1980s. She got her start at only 19 and quickly landed a series of interviews with Arkansas governor Bill Clinton. Millwee claims Clinton was often flirtatious but things escalated when the Governor visited her station. Millwee says she was editing footage in a small isolated room when Clinton allegedly began massaging her shoulders and then tried to touch her breast. "I was just stunned," she told Breitbart News in 2016. "I froze."

Millwee says she backed off the future POTUS but says things escalated a week later. "He came in behind me," she alleged. "Started hunching me to the point that he had an orgasm. He's trying to touch my breasts. And I'm just sitting there very stiffly, just waiting for him to leave me alone. And I'm asking him the whole time, 'Please do not do this. Do not touch me. Do not hunch me. I do not want this."

Millwee self-published a book in 2010 where she tells a much less salacious tale about being cornered by Clinton and receiving some unwanted touching of her shoulders. She told Breitbart News she downplayed the alleged assault because she wanted the book to be something she could "proudly tell people about ... at church." Breitbart also noted none of the interview footage Millwee describes exists, but a colleague says Millwee indeed interview Clinton. Millwee also provided Clinton's signature on her reporter's notebook. According to Business Insider, Clinton has denied the allegations. 

"Too many lies are being told. Too many lives are being ruined. And, I think it's time for the truth to come out." That's what Kathleen Willey told 60 Minutes (via The Nation) in 1999 about why she chose to come forward with her accusations against Bill Clinton. Her story has been hotly disputed since.

In 1993, Willey was a volunteer working in the White House when she took a meeting with Clinton in the oval office to talk about a paid position, according to The Washington Post. Seems like a low level discussion for a president, but Willey alleges Clinton's true motives: "He touched my breast with his hand ... I was just startled ... He said, 'I've wanted to do this ever since I laid eyes on you.' I remember saying to him, 'Aren't you afraid that somebody's going to walk in here?'" Willey alleged Clinton then put her hand on his genitals. 

Oddly, Willey's husband, who was in financial trouble, according to CNN, died by suicide the very night of that meeting. He "walked into the woods and shot himself," leaving an apologetic suicide note. Willey would later raise suspicions about the similarity of her husband's death to that of Vincent Foster. Clinton eventually denied the assault allegations to a grand jury. Willey's friend in the White House also claimed she was asked by Willey to lie about the incident. Linda Tripp claimed Willey was romantically fixated on Clinton.

If you or someone you know is having suicidal thoughts, please call the National Suicide Prevention Lifeline at 1-800-273-TALK (8255) or text HOME to the Crisis Text Line at 741741

Then came the other, other woman confirmed to have had a tryst with Bill Clinton. In 1992, the tabloid Star broke a bombshell story claiming Clinton had carried on a 12-year affair with the Arkansas state employee, TV reporter, and part-time lounge singer Gennifer Flowers, according to The Washington Post. Star had "ambiguously damming" (whatever that means) phone conversations too. Mainstream outlets would pick up the allegation and it nearly toppled Clinton's entire 1992 campaign.

Clinton went on offense and sat down with Steve Kroft of 60 Minutes, Hillary Clinton at his side, her arm around him in support. Clinton claimed his relationship with Flowers was "very limited," and carefully called the specific allegations of a lengthy affair, false. Kroft pressed the aspiring president if he was "categorically denying" the affair. Clinton simply non-answered by referring to his earlier lies, "I've said that before," Clinton replied. Both Bill and Hillary would spend the rest of the interview blaming the media and insinuating Flowers had simply sold the story out of greed — though Flowers was indeed paid by Star. 

However, once again, the ongoing Paula Jones litigation would undermine Clinton's story, forcing him to admit under oath he did have "sexual relations" with Flowers, according to The Washington Post. Clinton would dispute Flowers' accusation in part, saying there was only one encounter, all the way back in 1977 — two years after he wed Hillary Rodham.

Beyond the sex scandals, Bill Clinton is also known to enjoy the sight of a pretty lady.

In 2018, the world lost legendary soul singer Aretha Franklin. At the funeral, Ariana Grande was tapped to perform Franklin's classic "(You Make Me Feel Like) A Natural Woman." For the ostensibly solemn affair, Clinton was conveniently seated right behind Grande, and beside civil rights icon Jesse Jackson. The former president was captured on video looking anything but bereaved. His mouth hung slightly agape in a kind of admiring half-smile as he took in Grande's songbird stylings. "The look on Bill Clinton's face is priceless. It's familiar but priceless," commented Kelly Jane Torrance, deputy managing editor of The Weekly Standard, in an appearance on Fox News (via Newsweek).

But it was a clip of Clinton seemingly staring at someone else (and getting the death glare from Hillary Clinton) that caught fire. Following Donald Trump's inauguration in 2017, there were rumors of lifelong Democrat Clinton supposedly ogling Ivanka Trump. In a viral video, Hillary appears to catch her husband looking. The long-suffering former first lady turns to Bill, bores two holes in his head and then looks away with a bemused grin, of perhaps, disbelief, or maybe resignation. However, as the Daily Mail pointed out, "It is impossible to independently verify from the video" who or what Clinton was gawking at.