On June 4, 2003, a federal grand jury in Manhattan indicted Stewart and her former broker, Peter Bacanovic, on nine criminal counts. The government alleged that, by selling when she did, Stewart avoided losses of $45,673.

I remember the case but didn’t know the details. A $45k loss would be pretty devastating to me but I suspect with her net worth at the time that wouldn’t have been a very big deal. I worked a data entry job during college at a small local brokerage and remembered they were regularly discussing selling stocks at a loss for tax purposes with clients, and some of them would’ve been in that neighborhood.

Given everything this has cost her, it sounds like her broker should’ve just taken the loss and moved on.