The Saddest Things About Martha Stewart

Unless you've been living under a rock, you no doubt know the name Martha Stewart. The lifestyle guru has taken the world by storm since releasing her first book "Entertaining" in 1982. Since then, Stewart has become an award-winning author of several helpful how-to books, an Emmy-winning TV show host, an entrepreneur, and the founder of Martha Stewart Living Omnimedia.

Though many appreciate Stewart's valuable advice on cooking, gardening, hosting, housekeeping, and more, her private life is possibly even more fascinating. Consumers can't get enough of her surprising celebrity friendship with Snoop Dog and public feuds with fellow lifestyle influencers like Gwyneth Paltrow. And, of course, Stewarts' five-month stint in prison filled headlines in the early 2000s.

But there's much more to Stewart's life than her successes, controversies, and celebrity. In her own words, "I have survived the rigors of time, of marriage, of childbearing, of building a business from scratch ... I have survived very nicely, and I think I make the most of it (via People)." Though she seems to always come out on top, that doesn't mean things have been easy. Throughout the years, Stewart has overcome many hardships and learned to cope with loss.

Before becoming a household name, Martha Stewart was born Martha Kostyra to Martha and Edward Kostyra in Jersey City. She took the last name Stewart when she married Andrew Stewart in 1961. The pair met on a blind date when she was working as a model, and he was studying law. She was only 19, and he was 23 when they exchanged vows. They stayed married from 1961 to 1990, having their only child, Alexis Stewart, in 1965. During that time, Martha started to build her lifestyle empire, but their union was less idyllic than the glossy image they projected.

In an unauthorized biography on the domestic goddess, "Just Desserts," Jerry Oppenheimer asserted they had a rocky relationship and that Martha treated Andrew badly. "Martha would start arguments over the most trivial subjects, and they would go on and on and on," a source close to the couple told Oppenheimer. "There were times when there was utter and complete tension and long hostility-filled silences between them that you could cut with a knife," the source continued.

On top of all those arguments, the couple was reportedly unfaithful to each other. A friend of the couple claimed to have overheard an argument between the two and recalled to Oppenheimer, "The subject of affairs came up ... Martha asked Andy for details, but he was reluctant to tell her anything other than to say yes, he had done that, and so had she (via Daily Mail)."

Martha Stewart's father died in 1979. Edward Kostyra worked as a pharmaceutical salesman and fathered six children, of whom Stewart was the second to oldest. The loss of her father was particularly heartbreaking because of how close they were. During a Larry King interview, Stewart recalled how her father instilled her love of gardening and her work ethic by instructing her to remove the grass from their cobblestone path when she was three. "So I sat out there all day, you know, and I became his pet because of that," she said.

Speaking about their special relationship with Makers, Stewart said that although her father was busy, he always made time when she needed him for something. "I was his favorite child," Stewart said. "It's odd to say, but I was definitely his favorite child." She explained that her father would make himself available whenever she needed someone to take her somewhere or to explain "the facts of life" when she had questions that others wouldn't answer.

Her father was a huge inspiration in her life who taught her to work hard and aim high. The businesswoman recalled fondly, "He also always gave me the advice, 'Martha, you can do anything.' which was very positive advice for a young girl at that time." The loss of her father was deepened for Stewart because he passed before he could see just how much his daughter accomplished.

After years of marital difficulty, Martha and Andrew Stewart separated in 1987 and filed for divorce in 1990. Although their relationship wasn't perfect, Martha took the ending hard. After their divorce was finalized, she gave an optimistic spin to the public, telling People, "The life that I had is over ... And what has taken its place is better." But, according to those close to the issue, what happened behind closed doors was much more harrowing.

"I think that Andy leaving her made her feel undesirable," Martha's former friend Mariana Pasternak told the New York Post. Soon after their relationship ended, her ex-husband started dating and eventually married Martha's former assistant, making the end of their relationship even more painful. Pasternak recalled seeing Stewart hit herself and pull out chunks of her own hair due to the distress the divorce caused her.

The divorce was also very hard on their daughter, Alexis Stewart, who stopped speaking to her father after their split. Martha told New York Magazine that this was very hard on her ex-husband, who loves their daughter. "But she can't forgive him [for] his behavior," Martha said about Alexis's decision to maintain her distance.

In 2020, Martha spoke more candidly about how hard the experience was for her, saying, "Getting divorced was a terrible thing for me, because we were the first to divorce in my family ... And that we haven't spoken since the divorce is even more painful (via People)."

Although Martha Stewart is known for her illustrious career, her family life has always been more challenging. In her book "Whateverland: Learning to Live Here," Martha's daughter Alexis Stewart opened up about their less-than-perfect mother-daughter dynamic. "Martha was not interested in being kid-friendly," her daughter wrote. According to Alexis, although her mother built a career off her homemaking expertise, she grew up without any prepared food in the house and had to wrap her Christmas presents. And they didn't celebrate Halloween at all. "There were no costumes," Alexis wrote. "There was no anything. We turned off all the lights and pretended we weren't home."

Alexis also found it impossible to live up to her mother's standards, "If I didn't do something perfectly, I had to do it again," she said. "Martha does everything better. You can't win!" Between Martha's demanding career and perfectionism, the Stewart home was a difficult place for Alexis to grow up.

Martha herself admits that their relationship is far from perfect. Speaking to People, Martha explained she spent much of her daughter's childhood commuting to New York for her catering business. "I tried to involve her in everything, but the minute she could leave home and go to boarding school, she did. Our relationship has always been a difficult mother-daughter relationship." But despite those challenges and low points in their relationship, Martha added, "She would do anything for me, and I would do anything for her."

Though Martha Stewart is known for her impeccable taste and acumen as a businesswoman, she's often remembered for one of the lowest points in her life. Stewart was accused of insider trading after she received a tip from her former stock broker to sell ImClone's stock in 2001. She was indicted by a grand jury on counts of obstruction of justice, securities fraud, conspiracy, and making false statements. The trial was heavily publicized, tarnishing Stewart's reputation at the time and forcing her to resign from her position as CEO of her company, Martha Stewart Living Omnimedia Inc. Though, she did stay on as chief creative officer. After pleading innocent, Stewart was found guilty of conspiracy and obstruction in 2004. She was sentenced to five months in federal prison.

Years later, she spoke to Katie Couric about how harrowing her sentencing was to her. "It was horrifying, and no one — no one — should have to go through that kind of indignity," Stewart said. She didn't feel her time in prison helped her to grow or taught her anything, telling Couric, "That you can make lemons out of lemonade? What hurts you makes you stronger? No. None of those adages fit at all ... Nothing is good about it, nothing." On top of that, she had to endure being publicly "maligned," all while feeling she didn't deserve that treatment. "I mean, I was not a bad person," she said.

It seems Martha Stewart has had many tricky family dynamics over the years. Along with her messy divorce and challenging relationship with her daughter, Stewart also went for years without any contact from one of her siblings. Frank Kostyra is Stewart's younger brother, and the pair were estranged for five years. Following his sister's 2004 conviction, Kostyra told the New York Post that his heart went out to his sister. Watching her in federal court, Kostrya said, "I could see the horrible agony and heartache in her eyes and in her face." Although this was a distressing time for Stewart, seeing her in that position was what it took for Kostyra to remember their familial bond and finally heal the years-long rift between them.

Though he didn't share specifics on their falling out, Kostyra said, "Martha and I have always had a lot of sibling rivalry — I remember us lying on the floor biting and scratching as kids, trying to get each other to say, 'Uncle,' but she would never give in." After the trial, he wanted to be there for his sister despite their differences. He felt that many people misinterpreted Stewart as arrogant on the stand. "I just wish people remembered that Martha is a human, a precious human who's going through a tough, tough time," he said.

In 2014, Martha Stewart experienced a sudden and tragic loss when her younger sister, Laura Plimpton, died unexpectedly. Plimpton was the youngest of the six siblings, making her death all the more shocking. The 59-year-old mother of three died in a hospital after suffering a brain aneurysm at home. Although she was several years younger than Stewart, the sisters shared a close bond. Speaking to Larry King, Plimpton said, "I think Martha and I have a very special relationship. I was five when she got married, and all I wanted to do was be around her, her husband, and then when Alexis was born, I just wanted to take care of Alexis."

On top of their close family bond, Plimpton also became an employee of Stewart. The pair worked together for over 25 years, with Plimption writing, editing, and researching content for Stewart's company. In a memorial for Plimpton, published on her The Martha Blog, Stewart wrote that her youngest sister was "beloved by all." She added, "We are so sad but also happy that Laura had the foresight to donate so many healthy organs to needy people." In the post, Stewart asked readers to keep her late sister's three children and husband, Randy, in their thoughts. "Laura deserves the very best; she was an extraordinary mother, wife, and sister," Stewart finished the memorial.

Stewart endured yet another death in the family when her younger brother, George Christiansen, died at home of a suspected heart attack in 2017. Following his unexpected death, Stewart's spokesperson asked for privacy, telling Page Six, "Martha lost her youngest brother, George, suddenly and unexpectedly earlier this [past] week. The family requests that you respect their privacy during this time of sorrow." The death came just three years after Stewart lost her sister, Laura Plimpton, in an equally sudden manner.

Though his death was tragic, Stewart and Christiansen had a close relationship and many happy memories together. Christiansen was a contractor who led a relatively quiet life compared to his celebrity sister but was reportedly very close to Stewart. He appeared on her digital show, and his company, Pequot Remodeling, worked with Stewart to remodel her home, which she called Turkey Hill. Christiansen was quoted in the book "Being Martha," speaking about his fond childhood memories with his sister. "It was all about going and finding a piece of land and living off of it, learning how to get back to nature. Listening to banjos, listening to folk music, discovering Leadbelly and the Mamas and the Papas," Christiansen said. "We used to have the greatest evenings with a bunch of hospitable people. Martha would make pies and other things for the occasions."

For many pet owners, their animals are just like other family members, which certainly seems to be the case for Martha Stewart. Over the years, the famous entrepreneur has opened her heart and her home to a variety of pets, including several cats and dogs, canaries, peacocks, chinchillas, ponies, and more. Her farm allows her plenty of space to take in these pets, and she's always eager to share the adorable critters with her fans on social media.

Of course, raising so many animals means some of them have passed. Losing a pet is hard enough when they die peacefully of old age. Sadly, Stewart has had a few of her pets die in much more upsetting ways.

In July 2022, she shared an Instagram video of one of her favorite peacocks, Blue Boy, with an upsetting caption informing her followers that coyotes had killed the bird along with five other peacocks, including another favorite, White Boy. "RIP beautiful BlueBoy," Stewart wrote, going on to ask her followers for any advice to keep cayotes from getting to the rest of her birds.

Earlier that same year, her cat Princess Peony was killed by her own dogs. In a post about the beautiful cat's death, Stewart explained, "The four dogs mistook her for an interloper and killed her defenseless little self. I will miss her very badly."

Following her divorce, Martha Stewart has been relatively private about her dating life. She was known to date "Silence of the Lamb" actor Sir Anthony Hopkins for a brief period in the '90s, but speaking about their relationship, Stewart admitted she couldn't separate the actor from his frightening character Hannibal Lecter. Her next known relationship was with billionaire Charles Simonyi, which lasted 15 years (via Distractify).

Since then, Stewart has remained publicly single, but that doesn't mean she's not looking for love. It's just been difficult for her to meet her match. Speaking to Chelsea Handler, the domestic maven said she's had many crushes that lead nowhere because the object of her affection is married. "That's where I meet men," Stewart said, "They're all married to friends of mine or something like that." She also struggles to move on from those crushes because she always wonders if it's worth holding out for something to change. "You wanna believe that 'Oh, maybe this relationship that they're in is temporary," Stewart said, continuing, "I always think, 'Oh, gosh, couldn't that person just die?'" Handler clarified that the person Stewart was speaking of was the wife of her crush, which Stewart confirmed with the caveat that she didn't mean in a painful way.

Stewart also admitted to using dating apps for a time, though she has since given up on them. It seems like finding the right partner remains a challenge for Stewart.