Depends. If he's in a high tax state and it was all short term capital gains, then those gains are taxable as income. If he didn't keep the tax money separate a

Depends. If he's in a high tax state and it was all short term capital gains, then those gains are taxable as income. If he didn't keep the tax money separate and the market tanks 80% (which it did) he'd end up with losses that can't be offset because you can't carry losses backwards, only forward.