Martha Stewart

You know her for cookbooks, craft making, and insider trading. But Marth Stewart has also had her fair share of tax troubles—in 2002, she was ordered to pay over $200k in back taxes and penalties to the state of New York. The dispute in question: her New York state residency.

Stewart claimed she spent little time in the state and therefore had no residency. After all, New York has extremely high state income taxes, which is why so many New Yorkers try to spend over half the year in Florida, which has no state income taxes at all.

The issue went to court, and unfortunately for her, the judge found that Stewart did not have “credible testimony.” Why you may ask? Well, apparently, she commented in one of her cookbooks about the summer home she keeps in the Hamptons, and you can’t have it both ways. So the judge ruled in favor of the State of New York.

Lying became a theme for Stewart when just two short years later in 2004, a jury found her guilty of conspiracy, obstruction of justice, and two counts of making false statements to a federal investigator in the ImClone insider trading case. Stewart famously spent five months in jail for these charges.

However, she seems to have learned her lesson and rehabilitated both her outlook and career.

Josh Norris