Harvard law professor didn’t file a tax return for at least nine years

You may remember Ronald Sullivan from such comedy classics as If A Harvard Law Professor Who Chooses to Represent Harvey Weinstein Doesn’t Have His Discretionary Administrative Appointment Renewed, Then Gideon v. Wainright Has Been Overturned.

It turns out Prof. Sullivan apparently needed that lucrative side gig representing Weinstein in a pretty bad way, because according to our oppressive federal government he owes the IRS at least $1.23 million, which is the amount of the summary judgment entered against him yesterday in U.S. Tax Court.

I’m not a tax law expert in any way shape or form, but I’m vaguely aware that I’m legally required to file a federal tax return every year, which is something that our intrepid hero of the Intellectual Dark Web Opposing the Cancel Culture failed to do, per the opinion, for every year between 2005 and 2013, inclusive. (It’s unclear whether he’s filed tax returns since).

The IRS eventually took exception to this, and it filed substitutes for returns for Sullivan for the years 2012 and 2013. These SFRs concluded that he owed $1.23 million in taxes for those years. Now here’s where some of you tax law talkin’ guys and gals could help me out: How do you incur $1.23 million in unpaid tax liability over two years, if you’re a W-2 employee who does some 1099 work on the side? The published opinion says “the bulk of this assessed liability” appears to be for the sale of a house in Newton that Sullivan sold in 2013 for $1.865 million.

What I don’t understand is that, per the public records, Sullivan received no capital gains from this sale: He bought the house in 2007 for $1.895 million. It’s a 5,700 square foot nouveaux riche monstrosity that a developer scraped and flipped for $1.85 million in 2006. The buyers were apparently not quite riche enough, since they turned around and sold the property at a loss, considering transaction costs, to Sullivan just 15 months later.

Sullivan put down $900,000 cash on the transaction back in 2007, so I guess he was doing alright at the time. But then he got the Winthrop House dean gig in 2009 (see links in the first graph above for the details of that whole heart-rending saga) and decided to sell it, although he didn’t manage to actually unload it until 2013.

Now here’s what I don’t get: since Sullivan sold the house for less than what he paid for it, why would that sale generate any tax liability? One possible explanation for this mystery is that, per the linked opinion, Sullivan has refused, over the two and half years that this litigation has been going on, to provide any documentation to the IRS regarding his income, which he is legally required to do if he wants to challenge the judgment against him, and/or request some sort of payment plan. So maybe the Service is treating the sale price of the house in 2013 as 100% profit, and then there are a bunch of penalties that drive the whole thing up to the $1.23 million liability number? (Again I don’t know anything about tax law, except that bit about how you have to pay taxes every year).

I do realize that Sullivan could well have a huge amount of legitimate tax liability if he has been doing lots of highly paid independent contractor work since 2005, and just not paying any taxes on that income. But that possibility doesn’t seem to have anything to do with this particular judgment. (Note that Sullivan is representing himself in these proceedings, which is a bad sign for all sorts of reasons).

Who knows what’s really going on here, but at first glance this story seems to involve some baroque combination of elite impunity and deeply neurotic behavior, which are two things that often go together in the New Gilded Age like peanut butter and jelly.