CT attorney sentenced to 10 months in prison for failing to file tax returns

A Newtown attorney who neglected to file federal income tax returns for eight years while earning more than $5.6 million was sentenced Monday to 10 months in federal prison. U.S. District Judge Stefan R. Underhill in Bridgeport also ordered Michael Simes, 51, to serve one year of supervised release and pay nearly $2.9 million in restitution, according to the U.S. Attorney’s Office for the District of Connecticut. The sentence falls well below the 24 to 30 months called for under federal sentencing guidelines, as calculated in Simes’ plea agreement. Simes, a commercial litigator, pleaded guilty March 9 to three misdemeanor counts of willful failure to file a tax return. Each count carried a maximum penalty of one year in prison. He joined New York law firm Moses Singer as a litigation partner in September 2025, after running his own firm and previously serving as a partner at McGuireWoods. Prosecutors said Simes failed to file returns for the 2013 tax year and the 2016 through 2022 tax years, costing the IRS about $1.9 million. For 2016 through 2020, he requested extensions to October each year but still never filed or paid. Court filings show Simes received substantial income as a law firm partner during the years he didn’t file, before he joined Moses Singer. His biggest year was 2020, when he earned $972,195 in gross income and owed $339,329 in taxes, none of which he paid. He did file returns for 2012, 2014 and 2015 but paid only a fraction of the taxes he reported owing, racking up penalties and interest. Altogether, prosecutors said he owed more than $3.1 million in taxes, penalties and interest. The restitution figure reflects his current outstanding balance. It excludes $299,590 tied to the 2014 tax year, which the IRS has written off, according to the plea agreement. Under that agreement, Simes also agreed to cooperate with the IRS in paying all outstanding taxes, interest and penalties as a condition of his supervised release. Simes, who is free on a $40,000 bond, must report to prison Jan. 20, 2027. His attorneys, Kathleen Dion of Robinson & Cole and Michelle Merola of Hodgson Russ, filed a sentencing memorandum that included character references and a letter from a medical provider. The court sealed portions of it. The IRS Criminal Investigation Division investigated the case, which was prosecuted by Assistant U.S. Attorney Christopher W. Schmeisser.