When Taxes Don’t Go Away: Bankruptcy, Willful Evasion, and the Limits of a Fresh Start
By: Michael L. Moskowitz, Esq.
A recent decision from the United States Bankruptcy Court for the Southern District of New York offers a stark reminder that bankruptcy is not a cure-all—particularly when unpaid tax liabilities are the result of deliberate conduct rather than financial misfortune.
In United States v. Winick (In re Winick), Judge Philip Bentley held that more than $8.9 million in federal income tax liabilities were not dischargeable in a Chapter 7 case because the debtor had willfully attempted to evade his taxes within the meaning of Bankruptcy Code § 523(a)(1)(C).
At the same time, the court declined to impose the far harsher penalty of denying the debtor a discharge altogether under 11 U.S.C. § 727—underscoring the careful line courts draw between nondischargeable debt and the “death penalty” of bankruptcy.
The Facts: Lavish Spending, Minimal Tax Payments
The debtor, a highly successful New York commercial real estate broker, earned nearly $24 million in taxable income between 2012 and 2016. During those years, he lived an exceptionally lavish lifestyle—luxury residences, international travel, expensive gifts, and nearly $12 million in gambling losses—while paying only a fraction of the federal taxes he owed.
Rather than paying quarterly estimated taxes on his substantial commission income, the debtor directed that taxes be withheld only from his base salary, leaving millions in tax liabilities unpaid year after year. When the IRS attempted to collect, he repeatedly entered into installment agreements and submitted an offer-in-compromise—each of which temporarily barred enforcement—while allegedly misrepresenting that he had no income subject to estimated tax payments.
The Legal Issue: When Are Taxes Nondischargeable?
Under 11 U.S.C. § 523(a)(1)(C), a tax debt survives bankruptcy if the debtor “willfully attempted in any manner to evade or defeat such tax.” Courts require both:
- Conduct evidencing an attempt to evade or defeat taxes; and
- Willfulness, meaning voluntary, knowing, and intentional behavior.
The Second Circuit has long left open whether mere nonpayment of taxes is enough. In Winick, the court did not need to answer that question. The debtor’s conduct went far beyond passive nonpayment.
Why the Court Found Willful Evasion
Judge Bentley emphasized several factors that, taken together, established willful evasion:
- Systematic failure to pay estimated taxes, despite clear knowledge of the legal obligation to do so.
- Affirmative misrepresentations made to the IRS—through accountants and counsel—to secure installment agreements and block enforcement actions.
- Asset-protection behavior, including transfers of millions of dollars in business interests and luxury items to family members for no consideration, rendering the debtor effectively judgment-proof.
- Lavish discretionary spending, including gambling, even while substantial tax liabilities remained unpaid.
Although the debtor argued that a gambling addiction explained much of his conduct, the court rejected that defense, noting he had successfully structured his finances in other years to ensure taxes were paid before discretionary spending.
But No Denial of Discharge
Notably, the court did not deny the debtor a discharge under 11 U.S.C. § 727. The government alleged fraudulent transfers and false statements in the bankruptcy schedules, but the court found the evidence insufficient to meet the high standard required to strip a debtor of a discharge entirely. This distinction matters: nondischargeable taxes survive bankruptcy, but denial of discharge affects all debts and is reserved for the most egregious misconduct.
Key Takeaways
This decision carries important lessons for taxpayers and their advisors:
- Bankruptcy does not forgive intentional tax evasion. High income combined with nonpayment, deception, and asset shielding is a recipe for nondischargeability.
- Installment agreements and offers-in-compromise are not shields if obtained through misrepresentation. Courts will look behind them.
- Lifestyle choices matter. Courts closely scrutinize discretionary spending when assessing “willfulness.”
- Denial of discharge remains exceptional. Even serious misconduct may not trigger § 727 without clear evidence of intent to defraud the bankruptcy process itself.
Why This Matters for Clients
For business owners, executives, and high-net-worth individuals, this case is a reminder that how tax liabilities arise can matter more than how large they are. Courts distinguish between taxpayers overwhelmed by circumstance and those who knowingly choose not to pay while preserving lifestyle and assets. If you are facing significant tax exposure, proactive advice-before enforcement or bankruptcy-is critical. Waiting too long can permanently foreclose relief.
For individuals facing significant tax exposure, early and candid engagement with tax and insolvency counsel is critical. Once conduct crosses the line from financial distress into deliberate evasion, the “fresh start” promised by bankruptcy law may be out of reach.
If you or your clients are navigating complex tax liabilities or considering bankruptcy as a potential solution, it is essential to seek experienced legal counsel to protect your interests and ensure compliance with all applicable laws. Falcon Rappaport & Berkman’s Creditors' Rights & Bankruptcy Practice Group is well-equipped to provide strategic advice and representation tailored to your unique circumstances. Contact us today to discuss further.
DISCLAIMER: This summary is not legal advice and does not create any attorney-client relationship. This summary does not provide a definitive legal opinion for any factual situation. Before the firm can provide legal advice or opinion to any person or entity, the specific facts at issue must be reviewed by the firm. Before an attorney-client relationship is formed, the firm must have a signed engagement letter with a client setting forth the Firm’s scope and terms of representation. The information contained herein is based upon the law at the time of publication.