Having read the case summary, I’m both a little surprised by the outcome, and this is one lucky guy.
It sounds like the only reason he filed his tax returns was because of his federal contracting job, so he would otherwise continue to be what the IRS refers to as an ‘egregious non-filer’ and skirt the law the rest of us follow. It’s possible he didn’t meet filing requirements in any of those years based on income and filing status. This is an unknown X factor.
However, an honest belief you can’t file tax returns 15 years later after one return gets rejected? (2008 + 15 = 2023). Really? He doesn’t have any friends or anyone else he knows that file tax returns and/or complain about the IRS and all the rigamarole you sometimes have to go through to get issues straightened out?
“Furthermore, his possibly mistaken—but honest—beliefs that he could not file for subsequent tax years after 2008 or that he could not file the 2017
tax return are also somewhat probative of poor judgment” - Somewhat?
Where else might the ‘somewhat probative of poor judgment’ crop up on his job as a contractor?
The IRS generally only wants the six most current years’ worth of tax returns. It will be interesting to note if he files the other missing tax returns even though the IRS most likely will not pursue this.