Sketchy Things Everyone Just Ignores About Martha Stewart

For several decades, businesswoman Martha Stewart was known only for her role as a domestic goddess. Indeed, whether it was hosting her own TV shows, launching a range of best-selling books, or creating her own magazine — all of which bore her name, of course — the Barnard College graduate became the go-to guru for any homemakers wanting to keep up with the Joneses. However, thanks to numerous professional and personal exposés, and the small matter of a jail sentence for lying in a federal investigation into insider trading, the once-untouchable star has become just as famed for her behind-the-scenes misdemeanors as her front-of-house guidance.

Besides her success as a powerful woman in business, Stewart has been involved in some disreputable scenarios that can't go unnoticed. From extra-marital affairs and exaggerated accounts to contract breaches and celebrity feuds, not to mention character assassinations from her former best friend and even her own daughter, Stewart's eventful life took a turn for the worse several times.

It's not just in the business world where Martha Stewart has exhibited behavior that could be described as sketchy. In her candid 2024 eponymous Netflix documentary, "Martha," the lifestyle guru freely admitted that she repeatedly cheated on her first and only husband, Andrew Stewart, during their 29-year marriage.

Remarkably, one of Martha's infidelities occurred while she was on their honeymoon in Italy. "He didn't know I was married," the star recalled of her dalliance with a "very handsome guy" in Florence. "I was this waif of a girl hanging out in the cathedral on Easter Eve. He was emotional. I was emotional. It's just because it was an emotional place. It was unlike anything I'd ever experienced."

Martha Stewart, who in 2022 name-dropped her famous Instagram crush, also confessed that she'd embarked on a "very brief affair" with an Irishman during her pre-fame years as a stockbroker. "It was nothing," she claimed. "I would never have broken up a marriage for it." But her husband wasn't exactly an innocent party, either. According to the businesswoman, Andrew also often strayed. The couple finally called things a day in 1990. Despite all their extra-marital indiscretions, Martha admits she found her divorce a painful experience.

In the 1970s, Martha Stewart launched a catering firm with Norma Collier, a former model who at the time was one of her closest friends. But backing up the claims that the lifestyle guru is something of a control freak, she soon tried to make it a one-woman show.

Indeed, according to Christopher Byron's 2002 exposé "Martha Inc.," Stewart would often agree to cater for events without her business partner's knowledge and pocket all the cash for herself. Collier later described her former pal as a "sociopath and a horrible woman, and I never want to encounter her again or think about her as long as I live."

While Stewart appeared to be tight-fisted and underhand in the business world, she was a little too generous in her personal life. Indeed, in Jerry Oppenheimer's 1997 biography of the star "Just Desserts," Collier also revealed that Stewart once offered Collier her other half, Andrew Stewart, to help satisfy her sexual desires. "I laughed and said, 'Martha you've got to be kidding,' and she said, 'No, he's really very good in bed.' I said, 'I'm not going to share your husband. It is bizarre,'" Collier allegedly told Oppenheimer.

Martha Stewart's world — and reputation as the nation's premier domestic goddess — came crumbling down in 2002 when she found herself embroiled in an insider trading scandal. Two years later, in a development that would previously have been unthinkable, she also found herself behind bars.

The trouble actually began at the end of 2001 when Stewart sold her stake in a biopharmaceutical firm, ImClone Systems, owned by longtime pal Sam Waksal. A few months later, the Securities and Exchange Commission launched an investigation into the sale over concerns that she and Peter Bacanovic, her stockbroker, had been privy to insider information. Indeed, soon after, the company founder also got rid of his stock, with the FDA's decision to reject a new cancer medication reportedly the catalyst.

Stewart, who'd worked as a stockbroker before finding fame, protested her innocence. But at a 2004 trial which inevitably caused a media storm, she was found guilty of several charges including obstruction of justice and conspiracy and sentenced to a five-month term in a federal prison. It could have been much worse, however. The judge dismissed the far more serious charge of securities fraud which could have resulted in a total of ten years' incarceration. Here's a closer look at the serious crime that landed Martha Stewart in jail.

In 2007, Martha Stewart tried to trademark "Katonah," — the name of the town she'd bought a 153-acre estate in seven years previously — for a new line of paints and home furnishings. The move, however, wasn't exactly appreciated by the locals.

In fact, both the Katonah Village Improvement Society and several members of the Ramapough Lenape Nation — the latter a Native American tribe whose 17th-century leader the town was named after — essentially waged war against the lifestyle guru, and were supported by a string of other organizations who believed Stewart was guilty of exploitation. "If I wanted to trademark 'Martha Stewart' and put out a line of tea towels, she would have me in court very quickly," the Morning Star Institute's president, Suzan Harjo, reasoned to CBS News. "She'd be saying, 'You can't use my name, that's valuable, that belongs to me.'" Cayuga Nation representative Clint Halftown, meanwhile, told the outlet, "If it's being done for profit, then of course it's offensive. Of all the names in the world and all the words, why can't she pick something out that's not offensive?" The protests appeared to work when Stewart withdrew her trademark bid later that same year.

While addressing her five months in prison for her eponymous Netflix documentary in 2024, Martha Stewart claimed that she'd once been subjected to a 24-hour period of solitary confinement in which she was also deprived of water and food. However, following the documentary's premiere, news emerged that the businesswoman may have been laying it on a little thick.

Stewart, who later disowned the documentary, told the cameras that she was punished for the crime of "lightly" touching the key chain of a prison guard. However, the Federal Bureau of Prisons subsequently stated that the Alderson Federal Prison Camp in which the star served her time at didn't actually have a solitary confinement unit.

"In cases where it becomes necessary to temporarily remove an individual from the general population, FBOP facilities may use secure observation areas under direct supervision," a statement from the organization read (via Newsweek) before insisting that all prisoners are fed and given water on a regular basis. "These allegations do not accurately reflect the conditions or the procedures that would be followed, as the FBOP remains committed to providing humane treatment and ensuring basic needs are met at all times." Here's a closer look at the most outrageous claims Martha Stewart has made about her time in prison.

After serving five months in a federal prison for lying to federal investigators about her involvement in the ImClone Systems stock trading scandal, Martha Stewart was also required to spend five months under house arrest. However, the empire builder appeared to believe that the usual rules didn't apply to such a wealthy, internationally renowned domestic superstar.

Indeed, instead of lying low at her vast New York estate for this period, Stewart made it crystal clear she was back in town, attending a public yoga session — an activity she'd done to help pass the time while incarcerated — and constantly driving around in her four-wheel Kawasaki Mule. The entrepreneur, who had already been given permission to shop for groceries, attend medical appointments, and go to church while sporting an electronic ankle bracelet monitoring her activities, inevitably caught the attention of the relevant authorities.

Stewart's behavior was deemed to have made a mockery of the house arrest system and despite her lawyers' argument that confinement was impacting the success of her eponymous lifestyle company, she was subsequently ordered to serve a further three weeks before gaining her full freedom.

Turns out Snoop Dogg isn't the only celebrity in which Martha Stewart has forged an unlikely friendship. However, the G-funk maestro's lengthy rap sheet looks positively scarce compared to the crimes committed by two other names in her circle.

Indeed, in 2009, Stewart attended a party celebrating the 40th birthday of P Diddy, Puff Daddy, Diddy, or whatever other ridiculous moniker Sean Combs was adopting at the time. And she couldn't have been prouder to have received an invite, posting a flurry of pictures from the occasion on her blog, including one with "my friend, Harvey Weinstein." Of course, fast-forward to the modern day and both the rapper and the movie mogul are firmly behind bars.

Weinstein was exposed as one of Hollywood's most sickening predators in a 2017 New York Times piece which essentially launched the #MeToo movement and has since been convicted of multiple sex crimes leading to a lengthy jail sentence. Combs, meanwhile, was sentenced to 50 months in prison in October 2025 for the transportation to engage in prostitution.

In 2012, news emerged that JCPenney was going to start selling a wide range of goods bearing Martha Stewart's name having bought a large share in her eponymous lifestyle company. Of course, this didn't exactly go down well with the department store rival Macy's, who were under the impression they had exclusivity with the domestic goddess.

Indeed, in 2006, Stewart had a signed a deal with Macy's which stated that certain Martha Stewart Living items in their cookware, bed, and bath ranges would only be sold within their stores. As a result, they accused the entrepreneur of breaching her contract — which had since been extended to 2018 — and sought a preliminary injunction designed to prevent from her any further violations.

Following a year of legal discussions, the matter with Stewart was settled, although the details of exactly how remain undisclosed. "We are pleased to be able to put this matter behind us," a spokesperson for Macy's said (via CNBC). However, it took until 2017 for the two warring department stores to reach an agreement, too. 

Martha Stewart may have built her career on being the perfect homemaker, but according to a 2011 book published by her only child, Alexis Stewart, she didn't exactly make her own home the most loving of environments.

Indeed, in "Whateverland: Learning to Live Here," Alexis revealed that her famous mom was so disinterested in the big holidays that she was forced to wrap her own gifts at Christmas and hide from any trick and treaters on Halloween. "Martha was not interested in being kid friendly," she wrote before adding that she has a "very hands-off approach to child rearing." Elsewhere, the writer also claimed that she wasn't given a bra after reaching puberty, often saw her mother urinating without the bathroom door closed, and that she was strong-armed into being a perfectionist.

"Martha does everything better! You can't win," Alexis wrote. "If I didn't do something perfectly, I had to do it again. I grew up with a glue gun pointed at my head." Despite painting her in a deeply unflattering light, Martha was still more than happy to contribute to the memoir which her daughter also dedicated to her. "She's her own person," the lifestyle guru wrote. "She makes up her own mind. I sometimes try to offer advice, but if it's not taken, so be it."

You may think that as a founder of an empire which sold for $353 million — and who herself now has a reported net worth of $400 million — Martha Stewart would be content with her lot. However, according to several individuals who've been part of her vast lifestyle empire, the entrepreneur essentially lives her life by the motto, "more, more, more."

"Martha's an omnivore," an anonymous former executive told Vanity Fair in 2013. "She has however many houses. Even though she has a million pieces of garden ornaments, she buys more garden ornaments. Even though she has a million trees, she buys more trees. It's her genius and it's in some ways her downfall — that 'always hungry' thing." And it's not just dollars that Stewart has an insatiable appetite for, either.

Indeed, another executive told the same magazine that when it comes to business matters, Stewart finds it impossible to relinquish control. "The company should be more successful, but it is just limping along, because of her — because she doesn't trust anybody and she has to control everything," they said. Although the aforementioned did acknowledge their old boss had her charms in a one-on-one situation, she could turn "poisonous" if a third party was brought into the fold. Here's a further look at what Martha Stewart really spends her massive fortune on.

Martha Stewart seemed determined in the mid-2010s to get the millennials on board, joining forces with unlikely friend Snoop Dogg for a series of entertaining collaborations, voicing her no-holds-barred opinions on social media, and putting her name to a start-up centering on start-up kits. But she undid all her good work in one fell swoop in 2016 thanks to an interview with Luxury Listings NYC (via Page Six) in which she branded everyone born between 1981 and 1996 as lazy.

After acknowledging that millennials had become the most sought-after demographic in the business world, Stewart asked aloud who millennials actually are before serving up the controversial answer herself. "Now we are finding out that they are living with their parents," she said. "They don't have the initiative to go out and find a little apartment and grow a tomato plant on the terrace."

Although Stewart did concede that the younger generation had a difficult economic climate to deal with, she still appeared to misunderstand why they might not have the opportunities she had in her youth. "You have to strive for it," she said. "You have to go after it. I got married at 19, and I immediately got an apartment and I fixed it up. I was very proud of everything I did. I got the furniture at auctions for pennies."

We all know that Martha Stewart has a sharp tongue. Who can forget how she scolded one of her workers for having the sheer audacity to use the incorrect orange-cutting knife in her eponymous Netflix, documentary, for example? However, you might not be aware that she's also not afraid to get physical to express her disapproval, either.

Indeed, in a 2011 New York Magazine profile charting how Martha Stewart resurrected her career after going to prison, an anonymous insider claimed that during one particular board meeting, an enraged Stewart entered the room with a piece of kitchenware which she then slammed down on a table before moaning, "This is crap. I don't want my name on it." Fourteen years later, "Say Yes to the Dress" star Randy Fenoli alleged that he was once slapped by the businesswoman — albeit playfully — while she was guesting on the hit reality show.

Stewart herself has freely admitted that she can be a hard taskmaster. "I dislike waste," she said in Netflix's 2024 documentary, "Martha." "I dislike inefficiency, avoidance, impatience. I dislike people who think they can do more than they can do. I dislike not paying attention to details." In a piece of archival footage, she acknowledged, "I'm strict and I'm demanding and I'm all those good things that make a successful person" (via Rolling Stone).

Martha Stewart appears to be an equal-opportunity mean girl. Indeed, as well as making civilian members of her staff cry with her ruthlessness, the lifestyle guru has also directed her shady side toward various famous faces, too.

Just ask Gwyneth Paltrow, for example, who Stewart tried to put in her place in response to her Goop company in an interview with Net-a-Porter magazine (via Page Six). "[She] just needs to be quiet," Stewart said. "She's a movie star. If she were confident in her acting, she wouldn't be trying to be Martha Stewart." In the same piece, the star also called out Taylor Schilling for her portrayal of Piper Kerman in "Orange Is the New Black," remarking, "They could have done that so much better. That girl is not good enough."

Then there was the time that Stewart used Katy Perry's own lyrics in a gibe against her controversial space adventure. Indeed, after the singer returned from her mission aboard Blue's Origin NS-31, the domestic goddess uploaded a throwback clip to Instagram in which she recalled experiencing zero gravity aboard the G-Force One Boeing 727. "Do you ever feel like a plastic bag drifting through the wind?" she captioned the since-deleted post (via E! News), referencing Perry's monster hit "Firework," before adding, "In case you spaced out in 2007, Martha has always been ahead of her time."