A Newtown, Connecticut, attorney has been sentenced to 10 months in federal prison after admitting he failed to file federal tax returns for eight years while owing more than $3.1 million in taxes, penalties and interest. Michael Simes pleaded guilty in March to three counts of failing to file, and a federal judge in Connecticut ordered him to pay more than $2.8 million in restitution on top of the prison term. The case shows how a tax debt can keep compounding for years, quietly, before it turns into a criminal sentence rather than simply a larger bill.
Eight Years of Unfiled Tax Returns
According to the IRS Criminal Investigation release, Simes did not file federal income tax returns for 2013 and for 2016 through 2022 — eight tax years in all — even though he continued practicing law and earning income during that period. He also filed returns for 2012, 2014 and 2015 but underpaid what he owed. U.S. Attorney David X. Sullivan of the District of Connecticut announced the case, which was prosecuted by Assistant U.S. Attorney Christopher W. Schmeisser. IRS Criminal Investigation, the agency’s law enforcement division, built the case by reconstructing years of income and filings for a taxpayer who had largely stopped generating the paper trail a normal filer produces every April. Simes pleaded guilty on March 9, 2026, to three counts of failing to file a tax return, a plea that came years after the earliest of the eight unfiled years. Failing to file a tax return is a distinct federal offense from filing a false one; the charge against Simes centers on the returns he never submitted at all, for years in which the release makes clear he continued earning substantial income as a practicing attorney.
Inside the kit: Simes’s case came down to eight years of missing paperwork that eventually caught up with him, and the free credit-freeze steps and an account and device inventory in the kit exist for the same reason — so records stay organized before a gap like that becomes a crisis. Open The Senior Fraud Defense & First-Hour Recovery Kit.
A $1,876,307 Tax Loss on More Than $5.6 Million in Income
Prosecutors calculated a tax loss to the IRS of $1,876,307 on gross income of more than $5.6 million that Simes earned during the years he failed to file or underpaid, according to the release. That gap between what he earned and what he paid is what elevated the case from a civil collection matter to a federal criminal prosecution. The $3.1 million he ultimately owed in taxes, penalties and interest reflects years of compounding on top of the original tax loss figure, and the $5.6 million gross income figure establishes that Simes had substantial earnings each year he failed to file, rather than the case resting on a single high-income year. Penalties and interest on an unpaid federal tax debt accrue continuously, which is a large part of why the final figure Simes owed, $3.1 million, is nearly double the $1,876,307 tax loss prosecutors calculated at the outset of the case.
Restitution of $2,871,676 and a Prison Date in January
Judge Underhill ordered Simes to pay $2,871,676 in restitution, an amount that is lower than the more than $3.1 million he originally owed, reflecting payments or adjustments made by the time of sentencing, though the release does not itemize the difference. Simes has been ordered to report to federal prison on January 20, 2027, to begin serving his 10-month sentence, followed by one year of supervised release. The gap between the September sentencing and the January report date is common in federal white-collar cases, giving a defendant time to arrange personal and professional affairs before a prison term begins. The one-year supervised release period that follows the prison term means Simes will remain under court oversight, including compliance with any remaining tax obligations, for months after he is released.
U.S. District Judge Stefan R. Underhill’s Sentence
U.S. District Judge Stefan R. Underhill handed down the 10-month sentence in federal court in Connecticut, closing out a prosecution that U.S. Attorney David X. Sullivan’s office pursued after years of nonfiling turned a compliance problem into a sentencing hearing. The release does not detail how the court weighed the guilty plea, the $1,876,307 tax loss or Simes’s professional standing in arriving at the specific 10-month length, only that Judge Underhill imposed it alongside the $2,871,676 restitution order. IRS Criminal Investigation’s financial reconstruction — piecing together a defendant’s actual income from records other than the tax returns he never filed — is what allowed prosecutors to put a specific figure, $1,876,307, on the tax loss rather than treating the case as an open-ended failure to file. Assistant U.S. Attorney Christopher W. Schmeisser prosecuted the case for the District of Connecticut, the same office that pursues unfiled-return and other tax-related prosecutions across the state. A licensed attorney’s failure to file for eight of ten years, while continuing to practice, is the kind of fact pattern IRS-CI singles out in its public releases specifically because it signals the debt was not the product of a single bad year but a sustained pattern the agency’s investigators had to reconstruct from scratch.
Keeping a Paper Trail Ahead of a Legal Problem
Eight years of missing tax returns is what turned Simes’s case from a paperwork lapse into a restitution order and a prison sentence, and the same kind of quiet gap — an account nobody is watching, a document nobody filed — is what lets any financial problem compound for years before anyone notices. Most households have no organized record of which accounts, devices and contacts matter most if something goes wrong.
The Senior Fraud Defense & First-Hour Recovery Kit opens with the first-hour recovery plan and the family code word for keeping that kind of response ready instead of scattered.
Read the first-hour recovery plan in The Senior Fraud Defense & First-Hour Recovery Kit.
This article was produced with AI assistance and checked against the primary source linked above.
Warren Cohen is a finance writer based in Phoenix, Arizona, covering personal finance topics including credit, banking, and beginner investing. He earned his degree in business administration from Arizona State University and began his career working in consumer finance, where he gained direct experience with lending and credit systems. He now writes for personal finance websites and fintech platforms, focusing on clear, practical content that helps readers make informed financial decisions.
