Former Winthrop Dean Sullivan Failed to File Tax Returns for Nearly a Decade, Judge Finds

The United States Tax Court found that former Winthrop House Faculty Dean Ronald S. Sullivan, Jr. failed to file income tax returns from 2005 through 2013 and failed to pay the Internal Revenue Service more than $1 million in an opinion released Tuesday.

The IRS brought the case in order to collect an outstanding tax balance from 2012 and 2013, which amounted to $1,231,775. Sullivan, who is also a Harvard Law School professor, wrote in a 2017 form he submitted to the IRS that he did not believe he should have to pay the assessed 2013 balance.

“I did not (nor have I ever made) enough money to justify a $1.2M tax,” he wrote.

USTC judge Albert G. Lauber issued a summary judgement — meaning the court did not hold a full trial — after Sullivan failed to respond to multiple requests that he provide evidence that the IRS incorrectly assessed his assets in determining his tax bill. Lauber ruled that the IRS is entitled to collect the money it believes Sullivan owes.

Sullivan, who represented himself in the case, did not immediately respond to a request for comment on the court’s decision Tuesday evening.

Sullivan made national headlines earlier this year after he decided to represent Harvey Weinstein in his criminal case while simultaneously serving as faculty dean of Winthrop House. Harvard College declined to renew Sullivan as faculty dean in May after a semester of student outcry over his decision to join Weinstein’s legal team. At the time, students argued his response to their concerns was inadequate.

Over the course of 2017, the IRS sent Sullivan three letters informing him he would need to file his 2012, 2013, 2014, and 2015 returns in order to contest the amount he was required to pay. At one point, the assigned IRS settlement officer scheduled a date for a telephone hearing; Sullivan did not call in on the appointed date, provide relevant financial documents, or provide tax returns. In total, the IRS sent Sullivan at least seven messages attempting to inform him of the outstanding tax balance.

IRS records showed that Sullivan also failed to file tax returns from 2005 to 2011, according to the court.

Lauber wrote in the opinion that the bulk of what Sullivan owed in 2013 likely stemmed from the sale of his former home in Newton, Mass. Sullivan sold the house for $1,865,000 that year. From 2009 to 2019, he and his wife Stephanie R. Robinson served as faculty deans of Winthrop House and lived in the deans’ residence overlooking the Charles River.

In 2018, Sullivan sent the IRS a letter petitioning the court to overturn the IRS’s decision, writing that he did not receive notice of the hearing dates or his missing tax returns.

In April, the court again requested that Sullivan provide to the IRS “on or before June 15, 2019, a statement showing all income he received for tax years 2012 and 2013 and the dollar amount of each deduction to which he believes he is entitled for each year.”

Sullivan did not subsequently provide the requested documents. The IRS then requested summary judgement, to which Sullivan also did not respond. Lauber wrote that Sullivan may now propose a plan to pay the outstanding tax bill, including paying in installments.

—Staff writer Shera S. Avi-Yonah can be reached at shera.avi-yonah@thecrimson.com. Follow her on Twitter at @saviyonah.

—Staff writer Delano R. Franklin can be reached at delano.franklin@thecrimson.com. Follow him on Twitter at @delanofranklin_.