The 8 Biggest Controversies In Martha Stewart's Career

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Martha Stewart is, without a doubt, one of the most iconic business moguls in America. The New Jersey-born tastemaker began her career as a model and stockbroker before making a fortune teaching others how to cook, host, and create beautiful homes through her extensive catalog of cookbooks, magazines, TV shows, and product lines. There's no doubt that Stewart, who became America's first female self-made billionaire in 1999, has lived a truly fascinating life.

However, wherever there's fame, money, success, and power, controversy is often not far behind — and Stewart is no exception. Over the years, she has weathered some serious ups and downs. In 2004, of course, Stewart even went to prison for a short spell, but that's not the only incident that has stirred up contention. Find out about some of Stewart's biggest controversies below — including details about her rocky relationship with her daughter, her extramarital affairs, highly questionable friendships, and financial transgressions.

We can't talk about Martha Stewart's controversies without mentioning the insider trading scandal that landed her a five-month stint in federal prison. Back in December 2001, Stewart sold her 3,928-share stake in the biopharmaceutical company, ImClone Systems, which was owned by her close friend, Sam Waksal. On the surface, there's nothing illegal about selling shares. However, in 2002, federal authorities questioned Stewart about why she sold when she did. 

Stewart was later accused by the Securities and Exchange Commission (SEC) of offloading her stock because she was tipped off by her broker, Peter Bacanovic. Bacanovic knew that Waksal and his daughter, Aliza, were selling their own shares, suggesting that something was awry at the company. As it turned out, the U.S. Food and Drug Administration (FDA) had just refused to review ImClone's new cancer drug. Because that news wasn't public knowledge when Stewart dumped her shares, she and Waksal were accused of illegal insider trading. Stewart was also charged with lying to investigators and tampering with evidence to cover her tracks.

The case went to trial in 2004, and despite maintaining their innocence, both Stewart and Bacanovic were found guilty. Each was sentenced to five months in prison — where the food certainly didn't live up to Stewart's standards — followed by five months of home confinement. In 2017, on Katie Couric's podcast, Stewart said prison was horrifying and reiterated her opinion that she did not deserve a custodial sentence.

It's not just accusations of insider trading that have landed Martha Stewart in hot water — she's also been strongly criticized for her choice of friends. No, we're not talking about her team-ups with Snoop Dogg (although he has had his fair share of controversies), but her relationships with Sean "P Diddy" Combs and Harvey Weinstein. In a 2009 blog post, Stewart bragged about the "fantastic time" she had at Combs' extravagant 40th birthday bash. She uploaded dozens of images featuring decorations, ballet dancers, event sponsors, and multiple celebrity guests. Her gallery also included a picture of herself with "my friend, Harvey Weinstein."

In 2017, a New York Times investigation exposed a decades-long campaign of sexual misconduct by the now-incarcerated Weinstein. By 2020, at least 100 women had publicly accused the film producer of abuse. The scandal was one of the catalysts for the "Me Too" movement, which saw numerous celebrities, including Stewart, open up about their experiences of sexual harassment and assault.

Since 2023, Combs has also faced allegations of similar serious crimes, including sexual assault, sex trafficking, grooming, racketeering, kidnapping, and forced labor. In July 2025, he was found not guilty of racketeering and sex trafficking; however, he was found guilty of transportation to engage in prostitution. In 2017, while playing a card game on an episode of "Martha & Snoop's Potluck Dinner Party," Combs joked with the hosts that his last words would be "I did it."

In her 2024 Netflix documentary, "Martha," Martha Stewart revealed that her marriage to publisher Andy Stewart, which lasted from 1961 to 1990, was full of infidelity. Stewart claims that Andy had multiple girlfriends during their relationship, including a young florist who was staying in a barn on their land at the time.

However, in the documentary, Stewart also confessed to having affairs of her own. She recalls having a brief fling with an Irishman, as well as kissing another man while on her honeymoon in Europe. Stewart alleges that Andy was unaware of either occurrence during their 29-year marriage, but according to her ex-husband, Stewart's affairs were the reason he chose to be unfaithful. It's worth noting that Stewart never remarried after her divorce from Andy in 1990. In fact, she claims she never wanted to end the marriage in the first place. Andy, however, went on to marry — and later divorce — Stewart's former assistant, Robyn Fairclough.

Martha Stewart has been in the hot seat over her questionable friendships, but she's also no stranger to a feud. One of her more high-profile spats has been with actor and Goop founder Gwyneth Paltrow, whom she has been throwing shade at for quite some time.

It all started in 2013, when Stewart first commented on Paltrow's lifestyle platform to Bloomberg TV. The video is no longer available online, but she reportedly said, "[Paltrow] wants to be a lifestyle arbiter. Fine. Good. I think I started the whole category of lifestyle" (via Refinery29). That same year, TMZ asked Stewart who was the better lifestyle coach between her and Paltrow, and she responded, "Oh, for heaven's sake. You have to live to be a coach."

Stewart wasn't done with Paltrow yet. In 2014, she reportedly told Net-a-Porter's Porter Magazine (via Page Six) that Paltrow "just needs to be quiet." She added, "If she were confident in her acting, she wouldn't be trying to be Martha Stewart." When questioned about Stewart's remarks during Fortune's Most Powerful Women Summit, Paltrow sarcastically shrugged off the comments before noting she was actually pleased that Stewart saw Goop as a competitor. In the years since, Stewart has continued to make both subtle and not-so-subtle digs at Paltrow. While being questioned about Goop on The Corp podcast in 2019, Stewart wished all young entrepreneurs well, pointedly adding that she hoped they came in many forms — whether they be movie stars or hardworking women like herself.

Despite serving time behind bars, Martha Stewart's legal troubles didn't end in 2004. Her media and merchandising conglomerate, Martha Stewart Living Omnimedia Inc., faced multiple lawsuits in the years that followed. 

In 2012, Macy's took Stewart's company to court for breach of contract, alleging it had exclusive rights to product designs being sold by rival department store chain J.C. Penney. Just a few years later, Martha Stewart Living Omnimedia Inc. was sued again by R.R. Donnelley & Sons, the printer of her lifestyle magazines. R.R. Donnelley & Sons claimed it had been guaranteed $28.6 million in manufacturing revenue from two of Stewart's magazines, Martha Stewart Living and Martha Stewart Weddings. However, Stewart's company had apparently failed to honor this agreement, costing the printer millions of dollars and prompting them to seek $7.7 million in damages. Overall, it was a rough year for Martha Stewart Living Omnimedia Inc. 

At its peak in 1999, the company had been valued at $2 billion; however, it ultimately sold for just $353 million in 2015. The fall in value was partly blamed on Stewart's legal issues, including the insider trading scandal, and the company's failure to modernize for the digital age.

Martha Stewart tends to say what's on her mind; that much is evident from the comments she's made about Gwyneth Paltrow over the years. However, the Goop founder isn't the only one who's been the subject of Stewart's ire. In 2016, she also took aim at millennials. Per Inc., she told the now-defunct real estate magazine Luxury Listings NYC that businesses are targeting millennials, but that this generation "doesn't have the initiative to go out and find a little apartment and grow a tomato plant on the terrace."

She added that she understood economic circumstances were difficult but then implied that millennials weren't doing enough to help themselves move out of their parents' homes. In the same interview, she claimed that restaurateur David Chang told her that millennials knew nothing because they grew up without teachers.

Interestingly, Stewart is popular with Gen Z, the generation after millennials. A 2025 Pinterest trends report revealed a surge in searches for "Martha Stewart aesthetic" among younger users. It appears many Gen Zers are embracing Martha Stewart-inspired lifestyles, seeking to reconnect with the world by spending their summers cooking and gardening.

Martha Stewart isn't just a businesswoman. She's also mother to a daughter, Alexis, who was born in New York City in 1965. Apparently, it wasn't easy growing up with a media mogul for a mom, though. In her 2011 book "Whateverland: Learning to Live Here," Alexis spoke of her tumultuous upbringing and frustrations with her mother.

Alexis wrote, "If I didn't do something perfectly, I had to do it again," adding that she grew up "with a glue gun pointed at my head." She also says that Stewart wasn't overly maternal and didn't care for family-centered holidays. Alexis alleges she was made to wrap her own Christmas presents and wasn't allowed to play dress-up on Halloween. She also said that despite what many people might assume, there was never any food in the Stewart household. "Other people had food," she wrote. "I had no food. There were ingredients, but no prepared food of any kind."

Stewart herself has also acknowledged that, while she and Alexis love each other, their relationship hasn't always been straightforward. Nine years after Alexis' book hit the shelves, Stewart explained she had been very busy with her various ventures during her daughter's childhood. Stewart admitted they have always had a difficult relationship but made it clear that they would still do anything for each other.

From the Hamptons to Connecticut, Martha Stewart has owned multiple properties and lived in many different places throughout her life. However, Stewart's most recognizable home is almost certainly Cantitoe Corners, her sprawling 152-acre property in Katonah, Upstate New York.

Stewart's love of her Katonah home was made clear when she attempted to trademark the name for a line of homeware products in 2007. But there was one significant problem. Katonah is not just the name of a New York hamlet — it's also the name of a 17th-century Native American chief. The move upset many Native Americans, who saw the trademark attempt as offensive. Per The New York Times, Clint Halftown, a representative for the Cayuga Nation, said, "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 that's not offensive?"

Many Katonah locals were also concerned that Stewart's ownership of the trademark would impact their businesses. Ultimately, Stewart settled the dispute by agreeing to use the name only for her furniture line, which includes pillows, chair cushions, and mirrors.