Also possible that this could be related to his sale of Ars Technica. Massachusetts imposes its own capital gains tax, and he may have been liable for a significant portion of that, especially given that it sounds like it was MA domiciled. Or maybe not, but there's lots of ways that he could be legitimately liable for MA taxes while living in a different state.
Sounds to me like his beef could be with the Chicago CPA. CPAs are not created equal, and even the big 4 accounting firms make serious mistakes when things get complicated - has happened to me. Usually, when that happens, the CPA is responsible for fixing the problem (paying late fees, filings, etc.), but you're still liable for the underlying tax burden that they may have missed.
In any case, would be nice to know what the resolution was!
Sounds to me like his beef could be with the Chicago CPA. CPAs are not created equal, and even the big 4 accounting firms make serious mistakes when things get complicated - has happened to me. Usually, when that happens, the CPA is responsible for fixing the problem (paying late fees, filings, etc.), but you're still liable for the underlying tax burden that they may have missed.
In any case, would be nice to know what the resolution was!