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I imagine he could reach out to a tax attorney if he wanted to come clean.

Maybe it's possible for the tax attorney to reach out to the IRS and say "hey, I've got a client who hasn't filed tax returns in 30 years, and wants to come clean, but simply can't afford to pay 30 years of back taxes, penalties and interest." Maybe the IRS would be willing to reach a compromise where he is put on a payment plan for a reduced amount and stays current with his taxes going forward. From a collections standpoint that would seem to be the best option, however, from an enforcement and deterrence standpoint, the IRS may not want to waive anything.
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