‘I considered it a vacation’: 83-year-old Martha Stewart explains why her time in prison ‘was not that important’ — how America’s most famous homemaker rebuilt her riches and reputation

Embrace reinvention

Stewart began her culinary career in the late 1970s in the catering industry, quickly earning a reputation for serving high-profile corporate and celebrity clients. From cookbooks to launching the first issue of Martha Stewart Living magazine in 1990, she was known for her meticulous attention to detail and elegant style that set her apart in the lifestyle and homemaking industry.

Although she split from her husband Andrew Stewart in 1987 and divorced the same year her magazine launched, Stewart’s reputation as the ultimate housewife endured long after her marriage had ended.

But that image of perfection finally unraveled in March 2004, when she was convicted on charges including conspiracy, obstruction of justice and making false statements to federal investigators.

Following the verdict, Stewart was sentenced to five-months in prison, followed by two years of probation. The legal fallout extended beyond Stewart’s own reputation — it also had a significantly impacted Martha Stewart Living Omnimedia. The company’s stock price dropped and Stewart was forced to step down from her executive roles, including CEO and chairwoman of MSLO.

After her release, many questioned what Stewart’s next chapter would look like.

“I had to climb out of a hole,” she recalls in her documentary.

But the woman who once symbolized perfection in America did climb out of that hole, motivating herself with two mantras: “Learn something new everyday. And when you’re through changing, you’re through,” she shared in the documentary.

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The comeback

While Stewart’s time in prison saw her slip from her status as a billionaire, she didn’t stay down for long. Just months after her release in 2005, she returned to television with The Martha Stewart Show and a spin-off of The Apprentice. She’s published 43 more books, launched a CBD line and in 2015, sold Martha Stewart Living Omnimedia for $353 million.

One of her bolder moves came through an unexpected collaboration with Snoop Dogg, who she met on the set of the Comedy Central Roast of Justin Bieber. In 2008, Snoop appeared on the The Martha Stewart Show, charming the audience as he learned to make creamy mashed potatoes while teaching Stewart some new slang. Their connection led to the creation of Martha & Snoop’s Potluck Dinner Party — showing their unlikely chemistry and introducing Stewart to a younger audience, helping her redefine her image and reach a new demographic.

By 2023, she was still making headlines as the oldest woman to appear on the cover of Sports Illustrated’s Swimsuit Issue at 81.

By embracing self-deprecating humor, and using her media appearances to win back audiences who appreciated her ability to laugh at herself and talk about her challenges, Stewart made a comeback — and she refused to let her time in prison define the rest of her life.

“I could’ve just been a miserable, has-been housewife, but I didn’t let that happen to myself. And I’m so happy I didn’t,” she says in her documentary.