Without more details the whole story sounds iffy. Since he did not give us more details but still shared his story I will speculate that he took advantage of what he thought were some clever tax loopholes in MA. Remember that hid did state very passingly that he has a presence in MA. Specifically this: >>Again, I hadn't lived there or worked there since 2003, but I did own part of a business that was headquartered in…
The US taxes its citizens even outside of their own jurisdiction. It wouldn't surprise me if MA taxed people that still made money in MA.