To say Martha Stewart had it all around the time of Y2K would be a severe understatement. But the head of a media empire bearing her name—one that made her a billionaire the day of its initial public offering Bloomberg reported at the time—would eventually find herself behind bars. 

In 2003, the U.S. Securities and Exchange Commission charged Stewart and her former broker, Peter Bacanovic, with securities fraud. The SEC said Stewart “committed illegal insider trading when she sold stock in a biopharmaceutical company … after receiving an unlawful tip from Bacanovic.” 

Artist Elizabeth Williams always made sure to get the best available vantage point to draw Stewart—a seat on the extreme right of the front row.

“…I knew from there that I could get at least a side view of the lawyers speaking at the podium with Martha seated at the defense table,” she said. “Sometimes, I was craning my neck to see the witnesses between the heads of the jurors.

“There was no perfect seat in that courtroom as in most courtrooms, so you just did the best you could.”