Would claiming taxes on illegal activities be in violation of the Fifth Amendment?

Answer 1

If you want to be on the up-and-up, there are ways to claim it without incriminating yourself. The line 'other income' is a good catch-all that wouldn't disclose what you are doing. Remember that taxes is how they finally got Al Capone. :)

ANSWER: If you want to be on the up and up then don't involve yourself in illegal activities. Filing an income tax return will not legitimize your criminal behavior and only someone who makes a living off of statutory schemes would advise you to keep breaking the law in terms of the illegal activities you claim to be involved with and just mark "other income" as a good catch-all phrase to avoid incriminating yourself. Whether you are involved in legal or illegal activities if you file an income tax return you are most certainly incriminating yourself as to the tax liability involved with that tax return. If at a later date you determine you were never liable for the tax or subject to the revenue law to begin with good luck in extricating yourself from this statutory scheme as you have willingly and willfully incriminated yourself as being a taxpayer as specifically defined by the Internal Revenue Code and therefore subject to and liable for the tax.