Benjamin Z. Eisenstat is a Member in Caplin & Drysdale’s Washington, D.C. office, where he assists individuals and corporations in all manner of civil and criminal tax controversies. Over the past decade, Mr. Eisenstat has helped clients effectively return to tax compliance and move forward with their lives, whether that involves correcting tax issues prior to contact from the government, navigating IRS audits, or defending against criminal investigations.
Mr. Eisenstat has consistently achieved favorable results for his clients. In the criminal context, he has a strong record of persuading the government not to bring forth an indictment. And when cases have reached the plea and sentencing stage, Mr. Eisenstat has successfully advocated for substantial downward departures and variances from the sentencing guidelines, including a recent case where a client received a non-incarceratory sentence despite a guidelines range of 24 to 30 months in prison. In the civil context, he consistently helps his clients minimize their tax and penalty exposure. To that end, Mr. Eisenstat recently assisted a captive insurance participant in achieving a full concession from the IRS in a docketed case in the U.S. Tax Court.
Mr. Eisenstat is also active with the American Bar Association’s Section of Taxation. He is currently a Co-Chair of the Civil and Criminal Tax Penalties – Criminal Litigation Sub-Committee.
Mr. Eisenstat has experience representing clients in a broad range of cases including:
- All stages of criminal tax investigations conducted by the U.S. Justice Department and IRS Criminal Investigation from the pre-indictment phase, to the decision whether to plea or go to trial, to sentencing.
- Advising on highly-sensitive civil tax examinations of individuals or companies where potential fraud issues may arise (so-called “eggshell audits”).
- Representing clients before IRS appeals and the US Tax Court.
- Assisting clients in all stages of IRS examinations involving captive insurance arrangements, a current enforcement priority for the IRS.
- Assisting clients in criminal investigations or civil tax examinations specifically arising from unreported foreign accounts, assets or structures.
- Assisting clients in all manner of IRS collections matters, including negotiations of installment agreements and offers-in-compromise.
- Representing clients in connection with recently enacted qui tam provisions enabling private persons to bring claims for potential violations of District of Columbia and New York tax requirements, including cases that arise from allegations relating to a taxpayer’s state of domicile or residence.
- Assisting individuals and corporations in coming back into tax compliance prior to contact from the IRS.
Admissions & Education
Bar & Court Admissions
- District of Columbia
- New York
- U.S. District Court, District of Columbia
- U.S. Tax Court
LL.M., Taxation, Georgetown University Law Center, 2015
J.D., Georgetown University Law Center, 2014
B.A., University of Pennsylvania, 2010
Recognitions & Noteworthy
Honors & Recognitions
- Best Lawyers: Ones to Watch, 2024
Professional Activities & Affiliations
Member and Co-Chair of the Civil and Criminal Tax Penalties – Criminal Litigation Sub-Committee, Section of Taxation, American Bar Association
Member, The Tax Lawyer (during law school)
Newsroom & Publications
- 08.17.2023 | Awards & Rankings
- Bloomberg Tax Quotes Benjamin Eisenstat and Jonathan Black on Tax Court Ruling Potentially Increases Penalty Challenges04.27.2023 | Bloomberg Tax
- 11.12.2021 | Captive Insurance Times
- 11.10.2021 | Bloomberg Tax
- Benjamin Eisenstat Analyzes Voluntary Disclosure at Conference on IRS Act 22/60 Audits09.27.2023 | San Juan, Puerto Rico & VirtualRegister Now
- Benjamin Eisenstat Addresses Seeking Assistance to Avoid Penalties at Conference on IRS Act 22/60 Audits09.27.2023 | San Juan, Puerto Rico & VirtualRegister Now
- 02.11.2023 | San Diego, California
- Benjamin Eisenstat Addresses Important Developments in Criminal Litigation at ABA 2021 May Tax Meeting05.11.2021
Publications & Alerts
- 07.17.2023 | International Tax Alert
- Tax Court Rules that IRS Lacks Statutory Authority to Assess Penalties for Failure to File Form 547104.06.2023 | Tax Alert
- 03.07.2022 | ABA White Collar Crime Committee Newsletter, Article
- 05.12.2021 | IFC, Article
- 12.22.2020 | Captive Review, Article
- 04.13.2020 | Tax Alert
- 03.30.2020 | Tax Alert
- 04.20.2018 | Bloomberg Tax: Daily Tax Report, Article
- 03.14.2018 | Tax Alert
- 11.06.2017 | Tax Alert