Martha Stewart

Martha Stewart built one of the most recognizable lifestyle brands in American media, turning a basement catering business into a publishing, television, and merchandising empire. The 1999 initial public offering of Martha Stewart Living Omnimedia briefly made her, on paper, one of the first self-made female billionaires in the United States. Her name became shorthand for a particular ideal of domestic perfection.

That ascent stalled over a single stock trade. In December 2001 Stewart sold her shares in the biotech company ImClone Systems one day before the U.S. Food and Drug Administration publicly rejected a key ImClone drug. The sale itself drew scrutiny, but the case that ultimately brought her down was not about the trade. It was about what she told investigators afterward.

In March 2004 a federal jury convicted Stewart of conspiracy, obstruction of justice, and two counts of making false statements to federal investigators. She was never convicted of insider trading; the securities-fraud count tied to her stock was dismissed before the case reached the jury. She served five months at Federal Prison Camp Alderson in West Virginia, from October 2004 to March 2005, followed by home confinement.

The comeback was both commercial and cultural. Stewart returned to television, kept her company running, eventually sold the brand for hundreds of millions of dollars, and in her late seventies and eighties reinvented her public image entirely, partnering with Snoop Dogg and, at 81, becoming the oldest cover model in the history of the Sports Illustrated Swimsuit Issue.