Clinton had previously been confronted with allegations of sexual misconduct during his time as Governor of Arkansas. Former Arkansas state employee Paula Jones filed a civil lawsuit against him alleging that he had sexually harassed her. Lewinsky's name surfaced during the discovery phase of Jones' case, when Jones' lawyers sought to show a pattern of behavior by Clinton which involved inappropriate sexual relationships with other government employees.
In April 1996, Lewinsky's superiors transferred her from the White House to the Pentagon because they felt that she was spending too much time with Clinton. At the Pentagon, she worked as an assistant to chief Pentagon spokesman Kenneth Bacon. In September 1997, after Lewinsky told co-worker Linda Tripp about her relationship with Clinton, Tripp began to secretly record their telephone conversations. Lewinsky left her position at the Pentagon in December 1997, and in January 1998 submitted an affidavit in the Paula Jones case denying any physical relationship with Clinton. Though she attempted to persuade Tripp to lie under oath in that case, Tripp gave the tapes to Independent Counsel Kenneth Starr, adding to his ongoing investigation into the Whitewater controversy. Starr then broadened his investigation beyond the Arkansas land use deal to include Lewinsky, Clinton, and others for possible perjury and subornation of perjury in the Jones case. Tripp reported the taped conversations to literary agent Lucianne Goldberg. She also convinced Lewinsky to save the gifts that Clinton had given her during their relationship and not to dry clean a blue dress that was stained with Clinton's semen. Under oath, Clinton denied having had "a sexual affair", "sexual relations", or "a sexual relationship" with Lewinsky.
News of the Clinton–Lewinsky relationship broke in January 1998. On January 26, 1998, Clinton stated, "I did not have sexual relations with that woman, Miss Lewinsky" in a nationally televised White House news conference. The matter instantly occupied the news media, and Lewinsky spent the next weeks hiding from public attention in her mother's residence at the Watergate complex. News of Lewinsky's affair with Andy Bleiler, her former high school drama instructor, also came to light, and he turned over to Starr various souvenirs, photographs, and documents that Lewinsky had sent him and his wife during the time that she was in the White House.
Clinton had also said, "There is not a sexual relationship, an improper sexual relationship or any other kind of improper relationship" which he defended as truthful on August 17, 1998, because of his use of the present tense, arguing "it depends on what the meaning of the word 'is' is". Starr obtained a blue dress from Lewinsky with Clinton's semen stained on it, as well as testimony from her that the President had inserted a cigar into her vagina. Clinton stated, "I did have a relationship with Miss Lewinsky that was not appropriate", but he denied committing perjury because, according to Clinton, the legal definition of oral sex was not encompassed by "sex" per se. In addition, he relied on the definition of "sexual relations" as proposed by the prosecution and agreed by the defense and by Judge Susan Webber Wright, who was hearing the Paula Jones case. Clinton claimed that certain acts were performed on him, not by him, and therefore he did not engage in sexual relations. Lewinsky's testimony to the Starr Commission, however, contradicted Clinton's claim of being totally passive in their encounters.
Clinton and Lewinsky were both called before a grand jury. Clinton testified via closed-circuit television, while Lewinsky testified in person. She was granted transactional immunity by the Office of the Independent Counsel in exchange for her testimony.
Lewinsky's immunity agreement restricted what she could talk about publicly, but she was able to cooperate with Andrew Morton in his writing of Monica's Story, her biography which included her side of the Clinton affair. The book was published in March 1999; it was also excerpted as a cover story in Time magazine. On March 3, 1999, Barbara Walters interviewed Lewinsky on ABC's 20/20. The program was watched by 70 million Americans, which ABC said was a record for a news show. Lewinsky made about $500,000 from her participation in the book and another $1 million from international rights to the Walters interview, but was still beset by high legal bills and living costs.
In September 1999, Lewinsky began to sell a line of handbags bearing her name, under the company name The Real Monica, Inc. They were sold online as well as at Henri Bendel in New York, Fred Segal in California, and The Cross in London. Lewinsky designed the bags—described by New York magazine as "hippie-ish, reversible totes"—and traveled frequently to supervise their manufacture in Louisiana.
At the start of 2000, Lewinsky began appearing in television commercials for the diet company Jenny Craig, Inc. The $1 million endorsement deal, which required Lewinsky to lose 40 or more pounds in six months, gained considerable publicity at the time. Lewinsky said that despite her desire to return to a more private life, she needed the money to pay off legal fees, and she believed in the product. A Jenny Craig spokesperson said of Lewinsky, "She represents a busy active woman of today with a hectic lifestyle. And she has had weight issues and weight struggles for a long time. That represents a lot of women in America." The choice of Lewinsky as a role model proved controversial for Jenny Craig, and some of its private franchises switched to an older advertising campaign. The company stopped running the Lewinsky ads in February 2000, concluded her campaign entirely in April 2000, and paid her only $300,000 of the $1 million contracted for her involvement.
In March 2002, Lewinsky, no longer bound by the terms of her immunity agreement, appeared in the HBO special, "Monica in Black and White", part of the America Undercover series. In it she answered a studio audience's questions about her life and the Clinton affair.
By 2005, Lewinsky found that she could not escape the spotlight in the U.S., which made both her professional and personal life difficult. She stopped selling her handbag line and moved to London to study social psychology at the London School of Economics. In December 2006, Lewinsky graduated with a Master of Science degree. Her thesis was titled, "In Search of the Impartial Juror: An Exploration of the Third-Person Effect and Pre-Trial Publicity". For the next decade, she tried to avoid publicity.
During her decade out of the public eye, Lewinsky lived in London, Los Angeles, New York, and Portland but, due to her notoriety, had trouble finding employment in the communications and marketing jobs for nonprofit organizations where she had been interviewed.
In July 2014, Lewinsky was interviewed in a three-part television special for the National Geographic Channel, titled The 90s: The Last Great Decade. The series looked at various events of the 1990s, including the scandal that brought Lewinsky into the national spotlight. This was Lewinsky's first such interview in more than ten years.
On August 6, 2019, it was announced that the Clinton–Lewinsky scandal would be the focus of the third season of the television series American Crime Story with the title Impeachment. The season began production in October 2020. Lewinsky was a co-producer. It consists of 10 episodes and premiered on September 7, 2021. The season portrays the Clinton–Lewinsky scandal and is based on the book A Vast Conspiracy: The Real Story of the Sex Scandal That Nearly Brought Down a President by Jeffrey Toobin. The 28-year-old actress Beanie Feldstein plays Monica Lewinsky. In discussing the series and her observations on social media and cancel culture today in an interview with Kara Swisher for the New York Times Opinion podcast Sway, Lewinsky noted that:
Lewinsky started her own production company, Alt Ending Productions, and signed a first look deal with 20th Television in June 2021.
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