Depends on the details, but they may be in different buckets that you can't use to offset each other. Exercising the options is probably ordinary income, which can only be offset to $3k with short term capital losses.
wow. You could really fuck someone over by giving them something worth much more than their net worth and making sure it's damaged to worthlessness shortly thereafter.
That would generally be some variety of fraud. You can sue for damages, and there are tax laws and regulations dealing with losses due to bad acts like that.
