Michael Simes
Introduction
Michael Simes, 51, of Newtown, Connecticut — an attorney — was sentenced on September 14, 2026, by U.S. District Judge Stefan R. Underhill in Bridgeport to 10 months of imprisonment and one year of supervised release for offenses related to his failure to file tax returns and to pay more than $3.1 million in taxes, penalties, and interest owed to the IRS . United States Attorney David X. Sullivan’s announcement documents a decade-long pattern: Simes failed to file individual income tax returns for the 2013 tax year and the 2016 through 2022 tax years, producing a tax loss to the IRS of $1,876,307 on gross income of more than $5.6 million . He pleaded guilty on March 9, 2026, to three counts of failure to file a tax return, and is required to report to prison on January 20, 2027 .
Background Information
The non-filing spanned eight tax years. For 2013 and for 2016 through 2022, Simes filed no U.S. Individual Income Tax Returns at all, on gross income exceeding $5.6 million — income that generated a $1,876,307 tax loss to the IRS before penalties and interest . The release also documents a procedural evasion: for the 2016 through 2020 tax years, Simes requested filing extensions until October of each year, and still failed to file and pay the taxes he owed once the extensions ran out .
Three earlier years show the same pattern in lesser form. Simes did file returns for the 2012, 2014, and 2015 tax years, but paid only a fraction of the taxes reported as due, thereby incurring the substantial penalties and interest that the release says pushed his total owed beyond $3.1 million . The court ordered restitution of the presently outstanding balance: $2,871,676 .
The Controversy or Incident That Led to Their Cancellation
Convicted and sentenced.
The case against Simes is the documented record of a licensed attorney — a profession whose members are presumed to know the filing obligations everyone else is held to — declining to file or pay across a decade. The March 9, 2026, guilty plea resolved three counts of failure to file a tax return, and the September 14, 2026, sentencing imposed 10 months of imprisonment, one year of supervised release, and the $2,871,676 restitution order . The investigation was conducted by the Internal Revenue Service’s Criminal Investigation Division, and the case was prosecuted by Assistant U.S. Attorney Christopher W. Schmeisser .
Simes is released on a $40,000 bond in the interval before his January 20, 2027, report date . No statement from Simes is recorded in the release, and the announcement documents no claim that the non-filing was inadvertent — the guilty plea resolves the counts as charged failures to file .
Public Reaction and Consequences
The release records no public statement from Simes, his firm, or any bar authority; the documented reaction is institutional — an IRS Criminal Investigation probe of a tax professional’s own returns, a three-count federal plea, and a sentencing that orders $2.87 million in restitution . The consequences are the prison term beginning January 20, 2027, the supervised release year that follows, the restitution obligation, and a felony record for a practicing attorney . The release documents the tax loss on the unfiled years at $1,876,307, with penalties and interest bringing the outstanding balance the court ordered paid to $2,871,676 .
Current Status
Simes has been sentenced and must report to prison on January 20, 2027; he remains free on a $40,000 bond until that date . The judgment’s payment component — restitution of the presently outstanding $2,871,676 balance — survives alongside the custody term, and the release does not report any appeal or any resolution of the balance beyond the order to pay it . The supervised release term of one year follows the 10-month custody term .
Impact on Their Career/Life
For an attorney, the sentencing record is the career event: a federal felony plea to three counts of failing to file his own returns, a prison term, and a $2.87 million restitution order — documented across eight unfiled tax years and three underpaid ones . The case documents the extension-request pattern as part of the conduct — five consecutive years of asking for more time and then failing to file anyway — and the sentencing announcement makes the arithmetic public: more than $5.6 million in gross income, a $1.88 million tax loss, and a balance past $3.1 million once penalties and interest accrued . The IRS Criminal Division investigation that ended in a Newtown attorney’s 10-month sentence stands as the case’s documented institutional response .
Sources
- U.S. Attorney’s Office, District of Connecticut, “Attorney Who Failed to File Tax Returns and Pay More Than $3.1 Million Owed Sentenced to Prison”, September 14, 2026 — source