Questionable parenting and jail time: controversial things everyone just ignores about Martha Stewart

By Malavika Pradeep

Published Nov 20, 2022 at 09:15 AM

Reading time: 10 minutes

Cloud bread, pesto eggs, pancake cereal, pasta chips, smash burgers: ever since the broad launch of TikTok in 2017, the video-sharing app has evolved into a digital cookbook for viral recipes. Here, we’ve got sexy chefs plating aesthetic grub, silent vloggers hypnotising viewers with meditative ASMR, and even cucumber girls redefining the way we cut fruits.

Although TikTok has aided the rise of several creators and experts in the food and dining industry, the internet has always had a sweet spot for the OGs. While the 60s recorded Julia Child, the messy and forgiving chef who vowed to “take a lot of the la dee dah out of French cooking,” the 90s witnessed the ascent of a corporate overachiever-turned-domestic superachiever.

Cue the lights! In waltzes lifestyle whiz Martha Stewart, “America’s first self-made female billionaire.” For baby boomers, Stewart professionalised housekeeping with her expertise in “beautiful soups and how to make them, beautiful houses and how to build them, beautiful children and how to raise them.”

For millennials, her books became saturated with nostalgia for lost traditions and a simpler era. Meanwhile, for gen Zers, the kitchen sink idealist has now evolved into an ageless icon synonymous with thirst traps and NSFW subreddits. Who would’ve guessed, huh?


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Nevertheless, Stewart presides over the cult that she has built up from scratch, devoted both to her name and image. If you’re ever on a quest for recipes and stumble across her website, chances are that you’d end up following the same—given her footing as a seasoned lifestyle guru.

Although Stewart’s identity as a wise queen of domestication has catapulted her to a ‘soft-spoken gran’ status among gen Zers, the DIY diva has done some not-so-adorbs things in the past. From committing food crimes against humanity to raising her daughter with a “glue gun pointed at her head,” here’s the ugly truth behind the cookie-cutter exterior of Marthaland.

1. Lied to federal investigators and ended up in prison

One of the highly-publicised controversies surrounding Stewart is her insider trading scandal back in December 2001—when she avoided a loss of $45,673 by selling all 3,928 shares of her ImClone Systems stock after receiving material, non-public information from Peter Bacanovic, her broker at Merrill Lynch. The day after her sale, the stock value fell by 16 per cent.

In the months that followed, Stewart drew heavy media scrutiny. On 25 June 2002, CBS anchor Jane Clayson grilled the shrewd businesswoman on air about ImClone during her regular segment on The Early Show. In response, Stewart continued chopping cabbage and stated: “I want to focus on my salad.” Understandable.

Come 3 October 2002, Stewart resigned from her position on the board of directors of the New York Stock Exchange—which she held for a mere four months. The following year, she was indicted by the government on nine counts, including charges of securities fraud and obstruction of justice. She then voluntarily stepped down as CEO and chairwoman of Martha Stewart Living Omnimedia Inc. (MSLO), but stayed on as chief creative officer.

In March 2004, after a six-week jury trial, Stewart was found guilty of felony charges including conspiracy to obstruct, obstruction of an agency proceeding, and outright lying to federal investigators. Side note: during the investigation, Stewart told officials that she never received the insider information and instead had an agreement with Bacanovic to sell if the stock fell below $60. The one document to back up this claim was proven to be a forgery.

In July 2004, Stewart was sentenced to serve five months in a federal correctional facility and a two-year period of supervised release—including five months of electronic monitoring, which she didn’t have the best track record for compliance, but more on that later.

Stewart also agreed to a five-year ban from serving as a director, CEO, CFO, or any other officer role responsible for preparing, auditing, or disclosing financial results of any public company. What’s more is that, in June 2008, the UK Border Agency refused to grant her a visa to enter the country because of her criminal convictions.

2. Compared herself to Nelson Mandela and broke house arrest

The same day that she was sentenced to five months in the Federal Prison Camp in Alderson, West Virginia, a stoic Martha Stewart declared: “Many good people have gone to prison. Look at Nelson Mandela.” During an ABC interview, the then-62-year-old added: “I could do it. I’m a really good camper. I can sleep on the ground.”

During her time in jail, Stewart said her nickname was “M. Diddy.” In the minimum-security federal prison—which she dubbed “Camp Cupcake”—the business mogul spent her time doing what she does best: arts and crafts. According to The New York Times, Stewart’s jail stint involved everything from making “jam out of the crab apples on the tree” to a ceramic nativity set.

“You’re allowed to make three things in a year, I think, and I only had five months so I made an entire creche… the entire scene of the nativity,” she said. “So, I had many figures, something like 15 figures, and you’re only allowed to make three, but I persuaded them the whole nativity was one and they fell for it. You couldn’t just make three camels—you had to make everything.” Martha knows best, I guess?

Although she has since eased on her comments about the South African anti-apartheid activist, many believed that Stewart served a relatively-light sentence at a pretty cushy prison before being put on house arrest. And boy was her house arrest yet another controversy in Marthaland.

As it turns out, Stewart’s massive estate was not big enough to contain her for an additional five months. According to the New York Post, Stewart was allowed to leave her home for up to 48 hours per week, but only to attend work, church, doctor appointments, and food shopping.

However, she was spotted around town taking a yoga class and book shopping, among other leisure activities. The Post also reported that Stewart gave an interview in which she “mimicked the voice of her probation officer, bragged of knowing how to remove her electronic monitoring anklet, and spoke of leaving the confines of her house.” The result of her antics? Authorities forced Stewart to spend an extra three weeks of home timeout. Plenty of time to think about her actions, if you ask me.

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3. Has a terrible relationship with her daughter

Despite the routine homage that Stewart pays to the concept of ‘family’, she is not remotely interested in the messy contingencies that come along with the same. Although that’s understandable in the right context, Stewart’s daughter Alexis has previously admitted that being the lifestyle guru’s offspring is no easy feat.

In her 2011 memoir, Whateverland: Learn to Live Here, Alexis penned that Stewart was extremely tough on her. “If I didn’t do something perfectly, I had to do it again,” she wrote. “I grew up with a glue gun pointed at my head.” Alexis also levied claims against her mother including peeing with the door wide open. “I remember saying, ‘You know, now I have friends over! You can’t do that anymore! It’s gotta stop! My friends’ parents don’t do it! Give me a break here!’,” she shared.

Apart from her ill bathroom manners, Alexis claimed that the domestic goddess was a total Grinch during the holiday season. Forcing her to wrap her own Christmas presents, Stewart reportedly cancelled Halloween. “There were no costumes. There was no anything. We turned off all the lights and pretended we weren’t home,” Alexis admitted. Yikes, it seems like Stewart even had it out for all the children in her neighbourhood.

Stewart also wasn’t a fan of keeping any sort of prepared foods in the house. On these terms, Alexis went on to state that her mother was “a hoarder” who took “a very hands-off approach to child-rearing.” Heck, she further mentioned that Stewart refused to get her a bra when she hit puberty.

Although Alexis dedicated the book to her mother, who called the read “hilarious,” it seems that they still share a somewhat strained relationship. In her book, Alexis stated that Stewart is a terrible guest. “My mother will occasionally complain that I don’t invite her over for dinner,” she wrote. “But can you blame me? Because, sometimes this is what will happen: whatever I serve, she will sip it, taste it, make a face, and push it away.”

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4. Her problematic beef with Gwyneth Paltrow

If there’s one thing fans praise Stewart for, it’s the fact that she always “lets her intrusive thoughts win” against public figures and world news. However, this trait has only landed the business mogul in hot water and controversies beyond recovery—and one of her most notable feuds has been with American actress and Goop founder, Gwyneth Paltrow.

In 2013, Stewart told Bloomberg TV: “I haven’t eaten at Gwyneth’s house, and I’ve never seen how she lives. But if she is authentic, all the better. I mean, I certainly hope she is… She’s a charming, pretty person who has a feeling for lifestyle. She wants to be a lifestyle arbiter. Fine. Good. I think I started this whole category of lifestyle.”

The following year, Stewart took a more aggressive approach to establish her footing as a lifestyle queen by stating that Paltrow “just needs to be quiet. She’s a movie star. If she were confident in her acting, she wouldn’t be trying to be Martha Stewart.” A few months later, she also went on to design a dessert called “Conscious Coupling” for her Martha Stewart Living magazine. This was a clear swipe at Paltrow’s divorce from Chris Martin, in which the couple referred to the split as “conscious uncoupling.”

But Paltrow didn’t let Stewart have the last word. In retaliation, Goop followed suit by uploading a recipe for “Jailbird Cake” on its website. Spicy, indeed. Paltrow was later quoted saying: “No one has ever said anything bad about me before, so I’m shocked and devastated. I’ll try to recover.”

Then, in January 2020, Stewart once again decided to comment on Paltrow’s iconic vagina-scented candle by saying that “she’s trying to shush up the public to listen to her. And that’s great. I mean, let her do her thing. I wouldn’t buy that candle.”

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5. She’s also feuded with Blake Lively, Oprah Winfrey, and… Uber?

As it turns out, Stewart isn’t fond of Gossip Girl alum Blake Lively either. When Lively launched her own lifestyle company called Preserve in 2014, Stewart slammed the actress for emulating her. “Let her try,” she told HuffPost Entertainment. “I mean, it’s stupid. She could be an actress! Why would you want to be me if you could be an actress? I just did a movie yesterday, though—I can’t even tell you about it—but I want to be Blake Lively.” You see, Martha, your intrusive thoughts are having intrusions of their own here.

Fast forward to 2015, when Lively’s Preserve had to eventually shut down. At this point, Stewart offered minced words of encouragement by stating: “I’m sorry! I’m sorry! I know she made a big effort… Sometimes shuttering is good. Listen, she’s a movie actress. Why bother with commerce right now? She’s at the top of her career. I’m totally supportive, but you know what? Maybe you can’t do everything at the same time.”

In 2010, Stewart also took a veiled dig at Oprah Winfrey when she appeared on her talk show and discussed her prison sentence. “I used the time extremely well and I had visitors all the time, very good visitors,” Stewart said. “A whole lot of fabulous people came and visited me. I knew you were too busy.”

Lastly, the DIY diva called out the ride-hailing app Uber in 2018 after her first drive turned into what she described as a “mess inside and out.” According to Stewart, her first Uber didn’t show up. Meanwhile, the second car arrived ten minutes late and at the wrong address. She further claimed that it stopped halfway down the block and she “could not see the licence plate.”

When she successfully got inside the cab, Stewart then took issue about water bottles being stored in the back along with the dirt on the floor. Hey, Martha, have you ever considered the possibility that it may have been “a good thing”?

6. She once tried to trademark a town and Native American name

In 2000, Stewart purchased a 152-acre property in Katonah, a suburban town just north of New York City. Spending most of her time on the impressive farm, it’s safe to say that the business mogul adores her house. That being said, she also had an affinity for the name of the town in itself.

Come 2007, Stewart tried to trademark the name ‘Katonah’ for use on home furnishings, paints, and other products. Maybe she should’ve thought twice before being such a Halloween party pooper because surprise, surprise—her neighbours were not too pleased and fought to stop the trademark. In the end, they reached a compromise and Stewart could only use the name for furniture, mirrors, pillows, and chair cushions and not hardware, paint, lighting, and home textiles.

However, her stunt didn’t just anger the residents of the town. Stewart also insulted the indigenous people of the region. As noted by Mashed, Katonah is a Native American name belonging to a 17th century chief and the local Cayuga Nation wanted no part in sharing it with the magnate. At the time, a representative 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 out that’s not offensive?”

7. She’s allegedly terrible to work for

At this point, we’ve all established that Stewart is a bit of a perfectionist. It hence comes across as no surprise that she’s a control freak in professional settings. In 2013, a former MSLO executive told Vanity Fair that Stewart was destroying her own empire.

“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 shared. “Martha is delightful, charming, brilliant, fascinating—if you are in the room alone with her. You bring a third person in and it becomes poisonous. She has to dominate.”

The source went on to add: “Martha’s an omnivore. She just wants more, more, more. She has 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.”

Other people interviewed in the article concurred, stating that Stewart always put herself before the company. “[MSLO] was almost like two companies: one was the group of people who were trying to run a company that is publicly held. The other was Martha’s camp: the little girl who is trying to make sure that she gets as much money as she can,” they claimed.

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8. Her endless food crimes against humanity

As someone who repeatedly hammers her self-proclaimed status as a lifestyle queen in humanity’s collective consciousness, the truth is that Stewart is a really, really, really bad food photographer. So bad, in fact, that her fans have previously cried out in protest, questioned her sobriety, and circulated an intervention-style petition requesting that she “get the help she needs.”

Although her content has indeed witnessed an evolution in terms of aesthetics, her 2013 self just can’t be ignored—or should I say digested. Here’s a peak into some of the food crimes the diva has committed in the not-so-distant past:

At the end of the day, Stewart still doesn’t get why people don’t like her and is apparently clueless as to where and why some pesky rumours started in the first place.

“I don’t understand it. I write books. I’ve [published] beautiful magazines. I’ve done television shows that are devoted to good living. I don’t know,” she told Today. “Maybe because I’m confident. I think sometimes, ‘Maybe I’m too confident. Maybe I should have failed’. And maybe I should have, just, gone away and dug a hole and jumped in. You know—who knows?” Okay, now who’s going to sit Martha Stewart down and inform her of the countless listicles on her questionable behaviour circulating on the internet today?

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