Crystal Hefner’s legal team is taking issue with Holly Madison, claiming the former Playboy model is doing “serious harm” to the late Playboy mogul’s wife. Crystal’s attorney chastises Holly for her podcast interview with Hugh Hefner’s son Marston in a stop and desist letter, branding Holly’s comments as “malicious and intentionally misleading.” In a conversation on the May 12th edition of the “Girls Next Level” podcast, Holly, Marston, and Bridget Marquardt implied in the letter that Crystal kept Hugh “doped up” in his latter years so that she could exploit him financially.
The letter also adds, “Nothing could be further from the truth. As we understand it, Ms. Hefner was steadfast in her commitment to Mr. Hefner through his final days, ensuring that he was cared for and received the best medical attention available.” The model did not take advantage of Hugh’s physical and mental degeneration, according to Crystal’s attorney, and any suggestion to the contrary “is entirely false and will not be tolerated.”
Holly Madison Hits Crystal Hefner With Cease And Desist
The letter threatens to take legal action if Holly does not stop saying things like that in the future. Holly responded to the letter almost away, and she did it in a rather audacious way, posting on social media that she had used it to wipe her butt. She further expressed her disapproval of X in a letter that said, “Imagine running a free speech foundation and then sending someone a cease and desist for talking.” Crystal’s attorney told TMZ, “Ms. Hefner will not have her name and reputation tarnished by opportunists. We stand by the contents of the letter and will enforce Ms. Hefner’s rights to the fullest.”
Hugh’s former partners had previously engaged in a competitive relationship. Holly asserted in April that Crystal had almost plagiarized her biography, “Down the Rabbit Hole,” and that there were striking similarities between Crystal’s writing and her own. Crystal claimed in her book, “Only Say Good Things,” that she and Holly developed a rivalry during the production of “Girls Next Door,” which Holly said was probably accurate. Overall, the girls next door are at each other’s throats.
Playboy and Hugh Hefner have long been synonymous with luxury, lifestyle, and a provocative approach to sexuality. As a result, the man and his empire are still a subject of fascination and controversy, even years after Hugh Hefner’s passing. The founder of Playboy magazine transformed the publication into a global empire. However, a darker side emerged behind the glamorous façade of the Playboy Mansion and the iconic bunny logo.
From former girlfriends and employees of the famed Playboy patriarch to his wife Crystal Harris, many have spoken up about the terrifying and disturbing things that occurred at the infamous mansion. For example, Crystal has referred to her relationship with Hefner as “Stockholm Syndrome,” while also revealing her constant need to be outwardly perfect. Nonetheless, much more sinister allegations have reared their heads against Hef and his kingdom. Here are the worst allegations brought up over the years.
Over the years, several Playboy Bunnies and other women associated with the Playboy brand have come forward with accusations of sexual harassment and/or assault against Hugh Hefner. These allegations paint a disturbing picture of a culture within the Mansion that allowed inappropriate behavior to thrive. In an episode of the docuseries Secrets Of Playboy, identical twin sisters and former girlfriends of Hugh Hefner, Kristina and Karissa Shannon spoke up. They claimed that they engaged in sexual activities with Hefner against their wishes. Specifically, they insisted they were afraid to resist him, at the risk of angering him. Moreover, the twins claimed that Hef refused to use protection, and eventually, Karissa got pregnant. She was then forced to abort the child.
Drug Use At The Playboy Mansion
The Playboy Mansion and Hugh Hefner were notorious for extravagant parties and a lifestyle of hedonism. In the same vein, numerous reports and allegations have surfaced, detailing the rampant drug use within the Mansion’s walls. Former employees and guests have spoken about the pervasive drug culture and how the parties held inside the Mansion were drug-fueled. In 1973, Playboy Bunny Adrienne Pollack died of a quaalude overdose. As quaalude is often referred to as a sex drug, her death sparked suspicions about the use of drugs inside the Mansion.
Furthermore, past girlfriends of Hefner’s, particularly Sondra Theodore and Holly Madison, spoke up about this in Secrets Of Playboy. “Hef pretended he wasn’t involved in any hard drug use at the mansion, but that was just a lie,” Theodore said. “Quaaludes down the line were used for sex. Usually, you just took a half. Now if you took two, you’d pass out. It was such a seduction, and the men knew this… That they could get girls to do just about anything they wanted if they gave them a quaalude.”
Before the death of Hefner’s secretary Bobby Arnstein in 1975, the FBI investigated the rampant use of drugs at the Playboy Mansion. This was done in the hopes of finding evidence of drug trafficking. Although they found cocaine in Arnstein’s purse, there was no hard evidence that she was supplying Hugh Hefner and the Playboy bunnies with drugs. It wasn’t until 2022 that the matter was brought up again by Sondra Theodore. Additionally, in a shocking reveal, she claimed that she bought drugs for Hefner. “How many times did I pick up drugs for Hef? I don’t know, countless. Countless times… Luckily, I had angels watching over me and I never got caught,” she said.
Blackmail As A Result Of Extensive Monitoring
Former residents and employees of the Playboy Mansion have also alleged that there was an extensive network of hidden cameras. These were reportedly strategically scattered throughout the premises, including private living areas and social gathering spaces. The cameras recorded people in orgies and consuming hard drugs. Theodore, among others, alleged that Hefner had used these tapes to blackmail people into keeping quiet. “He lets the media into all these parties on purpose because usually they end up doing something they’ll regret,” she said. “So down the road, if anything is going to come out negative about him, he’d just say ‘I don’t think so – remember this?’”
Exploitation Of Bunnies
For decades, Playboy and Hugh Hefner have been accused of exploiting women and perpetuating objectification and unrealistic beauty standards. Behind the glamorous photo shoots and centerfolds of Playboy, however, also lay stories of financial exploitation. Some former Bunnies have come forward with allegations that they were either underpaid or not compensated at all for their work. Contracts were reported to be heavily skewed in favor of Playboy, leaving models with pay stretched out over a long period. Former Playmate Tylyn John also stated that the girls could not try to make money for themselves either. “They give you $5000 here and $2500 here,” she said. “They drag it out because you have to fulfill your duty before you get it all… You can’t do anything without their permission. Like if you were trying to make money off yourself? That was a no-no.”
Crystal Hefner has revealed that she will be changing her name back to her maiden name of Harris. It’s the latest step by the former wife of Playboy founder Hugh Hefner to distance herself from a man she has painted as abusive and manipulative. Appearing on the Miss Understood podcast, Hefner revealed that her surname was changed to match her husband’s soon after their 2012 wedding and that she didn’t get much say in the process. However, Hefner noted that it was starting the process of writing her memoir that got her thinking about the legacy of her name.
Furthermore, Hefner’s memoir, Only Say Good Things: Surviving Playboy And Finding Myself, is out now. As part of the memoir, Hefner reflected that looking back, she felt “brainwashed” at the time of her marriage to Hefner. Additionally, she noted feeling a sense of “Stockholm Syndrome” whenever she was able to “escape” the Playboy Mansion. No matter how many times she left the complex, she would always return under her own volition.
Los Angeles, CA – OCTOBER 25: Hugh Hefner and Crystal Hefner attend Playboy Mansion’s Annual Halloween Bash at The Playboy Mansion on October 25, 2014 in Los Angeles, California. (Photo by Charley Gallay/Getty Images for Playboy)
Born Crystal Harris, Crystal Hefner, first appeared on Playboy.com in October 2008. She was named as the “Co-Ed of the Week” while attending San Diego State. By January 2009, Harris was dating Hugh Hefner, who had founded Playboy in the 1950s. At the time, she was one of Hefner’s many girlfriends, a group that also included the Shannon Twins. Harris quickly became Hefner’s “number one girlfriend”, filling a role left vacant by Holly Madison.
In December 2010, Harris and Hefner became engaged but Harris would break off the engagement in June 2011. Despite this, she still appeared on the cover of the July issue of the magazine. The headline introduced her as “Miss Crystal Hefner”. However, the pair later reconciled and wed in 2012. They would remain married until 2017 when Hugh died. Crystal has since claimed that on his deathbed, Hugh warned her to “only say good things” about him and the magazine.
Hugh Hefner, the iconic founder of Playboy, and Crystal Harris, a former Playboy Playmate, captivated the public with their high-profile and often scrutinized relationship. With Hefner 60 years older than Harris, many looked down on their relationship and believed Harris was only after Hefner’s fortune. Nevertheless, the two pushed forward with their love and were married until 2017, when Hefner sadly passed away.
Crystal Harris has since claimed that she’s ready to drop Hefner’s last name, and published a tell-all memoir in January 2024, titled, Only Say Good Things: Surviving Playboy And Finding Myself. It’s been met with mixed reviews, but Harris definitely dropped a few bombshells. This article traces the fascinating timeline of their journey through love, commitment, and the challenges they faced.
2008-2009: Initial Meetings And Moving Into The Playboy Mansion
SAN REMO, ITALY – FEBRUARY 20:Kristina Shannon, Karissa Shannon, Hugh Hefner and Crystal Harris attend the Playboy party at the Morgana restaurant on the fourth day of the 59th San Remo Song Festival on February 20, 2009 in San Remo, Italy. (Photo by Venturelli/WireImage)
Hugh Hefner and Crystal Harris met at Hugh’s 2008 Halloween party. Crystal, 22 years old at the time, was introduced to Hugh, and despite the incredible age difference, the two hit it off pretty quickly. Their connection quickly evidently deepened, and Harris became a regular presence in Hefner’s life. That same month, Harris was named “Co-Ed Of The Month” on Playboy.com. By January 2009, Harris began dating Hefner and moved into the Playboy Mansion. There, she lived with Hugh and his other two girlfriends, the twin sisters Karissa and Kristina Shannon. In October of the same year, Harris made her debut on Girls Next Door. Two months later, she was crowned “Playmate Of The Month.”
2010: Hugh Proposes To Crystal Harris
(GERMANY OUT) Hugh Hefner and Crystal Harris at the TCM Classic Film Festival in Hollywood (Photo by Manfred Segerer/ullstein bild via Getty Images)
On Christmas Eve 2010, Hefner proposed to Crystal Harris with a 3.39-carat engagement ring and Harris said yes. Evidently, despite Hugh’s two previous marriages, he was still willing to give love a chance. Soon after, the couple announced their engagement to the public. Hefner posted on Twitter, stating: “When I gave Crystal the ring, she burst into tears. This is the happiest Christmas weekend in memory.” The news shocked many and the announcement of their engagement raised many eyebrows, especially considering their age gap. While Hefner was known for his many girlfriends, marriage was rarely a step for the casanova. As a result, many believed the 22-year-old was solely attracted to Hefner for his extensive wealth associated with Playboy.
June 2011: Crystal Harris Calls Off The Wedding
The wedding is off. Crystal has had a change of heart.
Even though Hefner was ready to spend the rest of his life with Harris, it seemed she did not feel the same way. Mere days before they were scheduled to exchange vows, Crystal decided to cancel the wedding. She went on to speak on Entertainment Tonight a few days later, explaining her decision. “I wasn’t the only woman in Hef’s life,” she said. “I didn’t feel comfortable in my heart knowing that and getting married to him because a marriage is between two people.”
HOLLYWOOD – APRIL 26: Hugh Hefner (L) and Crystal Harris arrive at the “Iron Man 2” World Premiere at El Capitan Theatre on April 26, 2010 in Hollywood, California. (Photo by Jeff Vespa/WireImage)
Just a month after the wedding was canceled, Crystal went on Sirius XM’s Howard Stern Show. There, she threw shade at her former fiancé and their sex life. “The sex lasted like two seconds. Then I was just over it,” she said. She ended by claiming she “walked away” and was “not turned on by Hef.” The information did not shock many, especially considering Hefner’s age at the time. Nonetheless, Hefner took the matter to heart and fired back in a now-deleted tweet. “For the record, I have sex on a weekly basis. And I did throughout my two-and-a-half years with Crystal.” The pair were ultimately believed to be over, and for months, did not exchange words publicly.
2012: Hugh Hefner And Crystal Harris Reconcile And Exchange Vows
BEVERLY HILLS, CA – AUGUST 07: Playboy founder Hugh Hefner (L) and TV personality Crystal Harris attend the Beverly Hills City Council and Playboy Enterprises, Inc.’s celebration of the return of Playboy headquarters to Beverly Hills on August 7, 2012 in Beverly Hills, California. (Photo by David Livingston/Getty Images)
Surprising many, Hefner and Harris reconciled in mid-2012. Moreover, they announced their renewed engagement. Harris tweeted that she was “his #1 girl again,” and that they were both happy. Hefner went more in-depth about how they reconciled in his own tweet, however. “It’s Mary O’Conner that brought Crystal Harris back. Crystal was miserable and said so. Mary told Crystal to write and tell me, which she did,” he wrote.
Hugh Hefner and Crystal Harris finally tied the knot on December 31, 2012, in an intimate ceremony at the Playboy Mansion. The wedding was attended by Harris’ family and Hefner’s four children. Unsurprisingly, it was reported that Crystal was required to sign an “iron-clad” pre-nuptial agreement. This was in an effort to safeguard Hefner’s massive fortune.
2013: Enjoying Married Life
HOLMBY HILLS, CA – MAY 09: (L-R) Crystal Harris, 2013 Playmate of the Year Raquel Pomplun and Hugh Hefner attend Playboy’s 2013 Playmate of the Year luncheon honoring Raquel Pomplun at The Playboy Mansion on May 9, 2013 in Holmby Hills, California. (Photo by Christopher Polk/Getty Images for Playboy)
Throughout 2013, Hugh Hefner and Crystal Harris were photographed attending various events together, portraying a united front. The couple’s lifestyle, which included a bustling social calendar and the glamorous world of Playboy, was closely followed by the media. Despite her previous confidence, Harris was elusive when discussing their intimate life post-marriage. Nonetheless, they remained heavily on the paparazzi’s radar that year. As time went on, media coverage on their lives began to dwindle.
December 2014: A Welcoming Christmas Tour
To share in the holiday spirit, Harris provided fans with an exclusive glimpse into the holiday festivities at the Playboy Mansion. Posting the tour on YouTube, Harris stated: “It’s the best time of year not just ’cause of gifts and stuff, but because of my friends and because of [my Christmas tree] and because it’s just such a cozy holiday. I love it. Christmas is my favorite holiday!”
September 2017: Hugh Hefner’s Passing
The legendary Hugh Hefner passed away on September 27, 2017, at the age of 91. Crystal Harris mourned the loss of her husband, expressing her grief and gratitude for the time they had together. Speaking to PEOPLE after the funeral, she said: “I will feel eternally grateful to have been by his side, holding his hand, and telling him how much I love him. He changed my life, he saved my life. He made me feel loved every single day.”
2018-2023: Crystal Harris’ New Life After Hugh Hefner
Crystal Harris, now widowed, continued her life outside of the Playboy Mansion. Unlike what many people assumed, Hefner did not leave a large chunk of his fortune for Harris. She also eventually moved out of the Playboy Mansion to Hawaii. Harris soon ventured into different pursuits, and her post-Hefner life became a subject of interest for those who had followed their relationship.
2024: Starting From The Beginning
Harris’ tell-all memoir was published in January 2024. It detailed many events that happened in the Playboy Mansion, and away from the public gaze. Harris also spoke about how she was forced to conform to Hefner’s views and wants, both physically and emotionally. In an interview with CBS Mornings, Harris admitted to never loving Hefner. She said: “I don’t think it was love. I did care for him. He was getting older and I know he wanted to protect his image… I felt sorry for him in a way and I felt that he really needed me.” As aforementioned, the memoir has polarized the public.
Crystal Hefner, the third and final wife of Playboy founder Hugh Hefner, has opened up about her experiences in the marriage ahead of a new memoir. Hefner said she felt like she was “brainwashed”, which led to her marriage to the magazine magnate. Furthermore, she noted feeling a sense of “Stockholm Syndrome” whenever she was able to “escape” the Playboy Mansion. No matter how many she times she left the complex, she would always return under her own volition.
In January 2022, Hefner revealed that she destroyed a “mountain of revenge porn” owned by her husband. This was corroborated by Holly Madison, who had lived in the Playboy Mansion between 2001 and 2008. Madison stated that she had been afraid to leave the mansion because Hefner held his revenge porn over the head of her and others. Other women have since come forward, revealing stories such as how Hugh would ply women with alcohol and drugs that he called “leg openers”. In late 2022, several women associated with Playboy, including a number who had resided at the Playboy Mansion, filed a class action lawsuit against the magazine about Hefner’s actions.
Born Crystal Harris, Crystal Hefner, first appeared on Playboy.com in October 2008. She was named as the “Co-Ed of the Week” while attending San Diego State. By January 2009, Harris was dating Hugh Hefner, who had founded Playboy in the 1950s. At the time, she was one of Hefner’s many girlfriends, a group that also included the Shannon Twins. Harris quickly became Hefner’s “number one girlfriend”, filling a role left vacant by the aforementioned Holly Madison.
In December 2010, Harris and Hefner became engaged but Harris would break off the engagement in June 2011. Despite this, she still appeared on the cover of the July issue of the magazine. The headline introduced her as “Miss Crystal Hefner”. However, the pair later reconciled and wed in 2012. They would remain married until 2017 when Hugh died. Crystal has since claimed that on his deathbed, Hugh warned her to “only say good things” about him and the magazine.
Crystal Hefner’s path in the public eye is a multifaceted narrative of glamour, business savvy, and personal evolution. As of 2024, her endeavors, extending beyond her initial fame as a model and public figure, have garnered her a net worth of $5 million, according to Celebrity Net Worth. Her story is more than a tale of financial success. It’s about leveraging a high-profile platform to create diverse opportunities and forge a distinct personal and professional identity.
From Playboy To Personal Brand: Hefner’s Career Development
Los Angeles, CA – OCTOBER 25: Hugh Hefner and Crystal Hefner attend. Playboy Mansion’s Annual Halloween Bash at The Playboy Mansion on October 25, 2014 in Los Angeles, California. (Photo by Charley Gallay/Getty Images for Playboy)
Crystal Hefner first entered the public consciousness through her association with Playboy, where her modeling career began. Her visibility in the magazine, and later as a Playmate, provided a launchpad for her career in the entertainment industry. However, Crystal ventured beyond modeling, channeling her public persona into various business ventures. Her foray into the fashion world with her own swimwear and lingerie line showcased her entrepreneurial spirit and understanding of brand development. This transition from model to entrepreneur highlighted her ability to navigate and capitalize on the business aspects of the fashion and entertainment industries.
Beyond Business: Hefner’s Personal Growth & Advocacy
LAS VEGAS – APRIL 04: Crystal Harris, Hugh Hefner, Kristina Shannon. and Karissa Shannon attend Hugh Hefner’s 83rd birthday dinner at Nine Steakhouse at the Palms Resort &. Casino on April 4, 2009 in Las Vegas, Nevada. (Photo by Denise Truscello/WireImage)
In addition to her professional pursuits, Crystal Hefner’s personal journey is marked by her advocacy for health and wellness, especially in light of her own health challenges. Her openness about her experiences with cosmetic surgeries and their complications has made her a voice for body positivity and health awareness. This advocacy work also adds depth to her public image. It paints her as an individual focused on business success and using her experiences to educate others.
Crystal Hefner: Cultivating A Legacy Of Empowerment & Entrepreneurship
LOS ANGELES, CA – JANUARY 16: Hugh Hefner (C) poses with Playboy Bunnies Playmate of the. Year 2013 Raquel Pomplun (2nd L) and Miss December 2009. Crystal Hefner (2nd R) at Playboy’s 60th Anniversary special event on. January 16, 2014 in Los Angeles, California. (Photo by Rachel Murray/Getty Images for Playboy)
Reflecting on Crystal Hefner’s journey to a net worth of $5 million in 2024, it’s evident that her real value lies in her transformation from a model and public figure to a businesswoman and advocate. Her legacy in the public sphere is characterized by her commitment to raising awareness about health and body image issues.
Her trajectory from the glamour of Playboy to a multifaceted entrepreneur and advocate is a testament to her resilience. Crystal Hefner’s net worth measures her financial success and symbolizes a career blending public visibility with advocacy efforts.
Hugh Hefner was the man behind Playboy magazine. Moreover, he is someone who is largely despised by those who criticize him. Although he claimed to be a beacon of women’s empowerment, those who knew him claimed otherwise. In the years since his death, many have noted just how bad of a person he was behind closed doors. From emotional manipulation to bizarre behaviors in private, the women who knew him were afraid of him. Now, his widow, Crystal Hefner, is telling all in a book called Only Say Good Things.
In this book, there are some pretty wild revelations in here. However, one is particularly shocking as it speaks to his priorities. Essentially, he took a lot of Viagra in his old age so that he could still have sex. If you abuse this drug for too long, there can be some severe consequences. For instance, Hefner eventually went deaf as a direct result of his Viagra usage. Although, as Crystal Hefner reveals, Hefner didn’t seem to care as it was just one ear. Moreover, he prefered having sex to having hearing.
LOS ANGELES – NOV 17: Hugh Hefner poses for a photo on Nov 17 2005 in Los Angeles, California. (Photo by Dan Tuffs/Getty Images)
Throughout the book, according to Page Six, Hefner also reveals how she had orgies at the Playboy mansion. As she describes, they were a humiliating experience. “It was embarrassing. I don’t know the most people there’d been in our bedroom at one time but — a lot. Pretty bad,” she said. “We were like, ‘Oh, now it’s your turn.’ Nobody really wanted to be there but I think in Hef’s mind, he still thought he was in his 40s, and those nights, the people, the mansion, solidified that idea. He felt, ‘I’ve still got it.’”
Needless to say, Hefner was a bit of an oddball, and his actions will not be remembered too fondly. Let us know your thoughts on the man, in the comments down below. Additionally, stay tuned to HNHH for more news from around the entertainment world.
