Got stuck with a huge tax bill on my stock options when Yahoo went under, took 10 years of brutal back to back contracts to pay it off. The state didn't care that I had nowhere near the opportunities again they just mercilessly hammered me for taxes until I paid it off a couple years ago but took nearly 15 years to pay off the tax debt and meanwhile I could invest in nothing else.
I've seen something similar to this in other responses in this thread, how exactly does one get a big tax bill for your stock options while simultaneously not being able to pay them off? I'm not understanding something about the situation.
Also in some cases especially with public companies they gifted you the options as income. That got marked as income even if the stock then tanked and you couldn't sell the stock for what the gifted value was.
There were various ways to get yourself screwed up.