Scarily bright, precise and analytical. No matter how complex the issue, he can unpack it so easily and in a way that you can understand.
—Tax client, Chambers 2024

Lawrence “Larry” Sannicandro focuses his practice on a broad range of federal and state tax disputes affecting individual private clients as well as their estates, trusts, and businesses (both public and private)

These disputes cover the full range of civil and criminal tax matters, including audits and examinations, administrative appeals, collection matters, summons proceedings, grand jury subpoenas, criminal tax investigations and prosecutions, litigation before the U.S. Tax Court, the U.S. Court of Federal Claims, federal district and appellate courts and state tax tribunals.

Larry has favorably resolved hundreds of tax disputes involving income taxes, estate and gift taxes, employment and payroll taxes, excise taxes, sales and use taxes, federal and state tax credits, and employee plan matters. Drawing on his background as a former estate and gift tax attorney for the IRS, Larry is uniquely well-versed in estate and gift tax planning techniques, the valuation of closely held businesses, and defending those planning and valuation techniques in disputes with tax authorities. Larry also works with clients to provide substantive legal advice on uncertain tax positions, identify and quantify tax-based risks, and proactively manage those risks through various procedural strategies.

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A dedicated pro bono advocate, Larry is the recipient of the American Bar Association (ABA) Section of Taxation’s Janet Spragens Pro Bono Award, the section’s highest honor for pro bono.  He is also a member of the IRS Advisory Council, a fellow of the American College of Tax Counsel, a vice chair of the ABA Tax Section’s Court Procedure Practice Committee, and a member of the Supreme Court of New Jersey District VA Ethics Committee. Previously, he taught corporate and partnership tax, tax practice and procedure, and legal ethics at several universities.

Representative Experience

Civil Federal Tax Controversy Litigation

  • Successfully represented a startup founder before the United States Tax Court and the U.S. Court of Appeals for the Fourth Circuit in a matter concerning: (1) the deductibility vs. capitalization of software developments costs; and (2) the deference owed to the IRS’s decision to exercise its non-enforcement powers and broaden the benefits of a statute through sub-regulatory guidance.
  • Acted as counsel to a lawyer and chairman of a private equity investment firm (as well as his spouse) before the United States Tax Court in a case of first impression concerning their: (1) entitlement to charitable contribution deductions; and (2) ability to avoid 40% gross valuation misstatement penalties due to the IRS’s noncompliance with I.R.C. § 6751(b)(1).
  • Persuaded the United States Tax Court that the terms of a closing agreement between the taxpayers and IRS precluded the IRS’s proposed assessment of income tax deficiencies relating to allegedly unreported foreign assets and income.

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  • Represented a closely held business owner before the United States Tax Court and the U.S. Court of Appeals for the Third Circuit in a matter concerning whether: (1) substance and form of corporate transaction were consistent; (2) netting of gains and losses in a corporate reorganization is allowed under I.R.C. § 356; and (3) the Tax Court was required to defer to contrary revenue ruling.
  • Successfully represented multiple estates before the United States Tax Court concerning: (1) the valuation of real estate holding, investment holding, and operating companies; (2) the deductibility (and valuation) of contingent liabilities; (3) whether transferred assets are includible in the decedent’s estate under I.R.C. § 2036; and (4) whether particular grants of interests qualified as “profits interests” with respect to which U.S. federal gift tax was owed.
  • Obtained full concessions from the IRS in docketed case before the United States Tax Court with respect to taxpayers who claimed benefits through Puerto Rico Act 22. The IRS conceded that (1) the taxpayers were bona fide residents of Puerto Rico, (2) the taxpayers’ income was properly sourced to Puerto Rico, and (3) there was no deficiency in income tax.
  • Acted as counsel to multiple tax matters partners of TEFRA partnerships and partnership representatives of BBA partnerships with respect to the partnerships’ entitlement to charitable contribution deductions or federal tax credits.
  • Obtained a full concession from the IRS following the filing of a summary judgment motion seeking to invalidate Treasury Regulations section 1.165-11(e) with respect to the claimed carryback of a disaster loss.
  • Served as counsel to various individuals before the U.S. district courts and United States Court of Federal Claims in (1) affirmative litigation to obtain refunds of income taxes or pursue a wrongful levy, and (2) defensive litigation to reduce assessments to judgment and foreclose federal tax liens.
  • Represented a Swiss resident before the U.S. District Court for the Southern District of New York and the U.S. Court of Appeals challenging the IRS’s enforcement of an administrative tax summons concerning the alleged nonpayment of taxes.
  • Served as counsel to multiple taxpayers before the U.S. Courts of Appeals for the Third and Eleventh Circuits, as well as the United States Tax Court, with respect to whether a tax return preparer’s fraud tolls the statute of limitations on assessment under I.R.C. § 6501(a).
  • Represented an estate and the decedent’s surviving spouse before the United States Tax Court with respect to whether a tax return preparer’s fraud precludes the suspension of interest under I.R.C. § 6404(g).
  • Obtained complete victory for taxpayer with respect to her ability to deduct relatively sizable medical expenses for Reiki and energy healing.
  • Acted as counsel to lawyer’s wife to obtain relief from joint and several liability (e., so-called “innocent spouse relief”) under I.R.C. § 6015(b) and (f).
  • Civil Federal Administrative Tax Controversy Matters
    • Successfully resolved at the individual level a global high wealth program audit of the founder of a private equity firm and family office involving the founder’s ability to qualify as a “real estate professional,” the entitlement to millions of dollars of net operating losses, the allocation of recourse and nonrecourse debt, and various other complex issues.
    • Obtained full concession from the IRS Independent Office of Appeals with respect to an executive’s entitlement to deduct significant charitable contribution deductions notwithstanding the alleged failure to secure a “qualified appraisal” by a “qualified appraiser” or an “appraisal summary” (IRS Form 8283) that meets all statutory and regulatory requirements.
    • Represented a financial institution with respect to the deductibility, as opposed to capitalization, of success-based fees in connection with its merger and acquisition activity. Matter resolved, without penalties, with a favorable allocation for the corporate taxpayer notwithstanding the failure to make a timely election.
    • Serve as lead tax controversy counsel to the partnership representative of a BBA partnership in connection with the IRS’s attempted recapture of low-income housing taxpayer credits.
    • Act as counsel to various high income nonfilers and, in multiple matters, secure abatement of all late-filing and late-payment penalties on the ground of reasonable cause.
    • Advise various closely held, midsized and large businesses, as well as their executives and managers, concerning the failure to pay employment and payroll taxes to the IRS and state and local tax authorities. In some matters, secure abatements of millions of dollars of related penalties.
    • Represent multiple commercial airline companies in connection with the failure to pay air transportation excise (as well as related) taxes, and advise members of the boards of directors concerning their potential exposure for the trust fund recovery penalty. Pursue abatements of millions of dollars of related penalties.
    • In connection with anticipated enforcement efforts by the IRS, advise clients on a broad range of substantive tax issues where the tax reporting position is uncertain.
    • Advise dozens of clients with respect to voluntary disclosures as well as reporting requirements under the Bank Secrecy Act and the Foreign Account Tax Compliance Act, including but not limited to FinCEN Form 114 and IRS Forms 926, 3520, 3520-A, 5471, 5472, 8621, 8858, 8865, and 8938.
    • Successfully handled hundreds of federal and State tax collection issues, including avoiding the trust fund recovery penalty and securing for clients abatements of civil tax penalties, innocent spouse relief, and collection alternatives, such as offers in compromise and installment agreements.
  • Civil State Tax Controversy Litigation and Administrative Matters
    • Represented a multinational software company before the New Jersey Tax Court and negotiated a favorable settlement agreeing that: (1) royalties paid by a subsidiary to a parent corporation were deductible and not subject to the addback provisions for New Jersey Corporate Business Tax (“CBT”) purposes; and (2) parent corporation was entitled to the domestic production activities deduction under the CBT and I.R.C. § 199.
    • Submitted to the New Jersey Appellate Division, on behalf of a nonprofit organization, an amicus curiae brief in support of the taxpayer’s position that assessments of sales and use tax against a responsible person were barred by the applicable statute of limitations.
    • Served as co-counsel to couple in Maryland Tax Court mounting constitutional challenge to the State of Maryland’s disallowance of the foreign earned income exclusion to Maryland nonresidents.
    • Obtained full concession by the New Jersey Division of Taxation concerning a fuel supplier’s alleged liability for the failure to collect and remit more than $19 million of New Jersey Motor Fuels and Petroleum Products Gross Receipts Taxes.
    • Successfully negotiated voluntary disclosures with the New York State Department of Taxation and Finance, the New York City Department of Finance, the New Jersy Division of Taxation, the Pennsylvania Department of Revenue, and the City of Philadelphia Department of Revenue.
  • Criminal Tax Controversy Matters
    • Secured non-custodial sentence, following plea agreement, for business executive concerning unreported income from cryptocurrency-related transactions; successfully persuading the federal government that tax loss should be reduced by approximately 90%.
    • Persuaded the U.S. Department of Justice Tax Division to not authorize prosecution against a closely held business owner concerning unreported income taxes.
    • Served as co-counsel to certified public accountant in post-indictment criminal tax proceeding involving the filing of false employment and income tax returns as well as conspiracy to commit tax evasion.
    • Represented various individuals and companies, including tax professionals, accounting firms, financial service firms, and other third parties, in responding to grand jury subpoenas.

Professional Highlights

Honors and Awards

  • Recognized for expertise in tax law by Chambers and Partners (2023 – 2024), Super Lawyers (2021)
  • Selected as Bloomberg Tax Portfolio Author of the Year (2023)
  • Served on Law360 2023 Tax Authority Federal Editorial Advisory Board

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  • Selected as a 2022 ROI-NJ Influencer: Law
  • Presented the 2020 Janet Spragens Pro Bono Award by the ABA Section of Taxation
  • Recognized as a 2018 Leader of the Bar by the New Jersey Law Journal
  • Awarded the 2016 John S. Nolan Fellowship by the ABA Section of Taxation
  • Presented the 2015 Pro Bono Award by the New York County Lawyers’ Association
  • Speaking Engagements*
    • Handling an IRS Examination, Practicing Law Institute, 3.24.2025
    • Navigating Federal Tax Litigation & Appeals: Recent Cases, Administrative Processes & Strategies for Counsel, Strafford, 3.18.2025
    • Careers in Tax Law, Quinnipiac Tax Law Society at the Quinnipiac University School of Law, 2.10.2025
    • International Taxation: Information Reporting & Penalties, 2025 D.C. Bar Tax Conference, 1.15.2025
    • Common Ethical Conflicts in Tax Practice, ABA’s 2024 Criminal Tax Fraud and Tax Controversy, 12.14.2024
    • Current Trends in International Tax Enforcement: Information Return Penalties and Updates to the IRS’s Voluntary Disclosure Practice, Tax Practice Pro’s International Tax Conference, 10.30.2024
    • To Retain or Not to Retain: Planning with Business Entities and Code Section 2036(a), NYC Estate Planning Council, 9.12.2024
    • Challenging Civil Penalties, NYU Tax Controversy Forum 6.27.2024
    • Nuts and Bolts of Tax Controversy 2024, Practicing Law Institute, 3.25.2024
    • Penalties in International Tax Practice – an Update, USA Branch of the International Fiscal Association, 3.21.2024
    • Nuts and Bolts of Refund Litigation, ABA Section of Taxation’s 2024 Midyear Meeting, 1.29.2024
    • Ethical Issues in Artificial Intelligence and Data Security: How Data Technology is Changing Tax Practice, ABA’s 2023 National Institute on Criminal Tax Fraud and Tax Controversy, 12.8.2023
    • Nuts and Bolts of Tax Litigation: Motion Practice, ABA Section of Taxation, 8.30.2023
    • Litigating a Remote Trial in United States Tax Court, ABA Section of Taxation’s 2023 May Meeting, 5.5.2023
    • Nuts and Bolts of Tax Controversies 2023, Practicing Law Institute, 3.27.2023
    • Remedying Missed Elections, Deadlines, and Claims: Section 9100 Relief and Other Strategies to Fix Missed Elections, Deadlines, and Claims, Strafford, 3.16.2023
    • Ethical Considerations in Preparing Tax Return Disclosures, ABA Section of Taxation, 2.10.2023
    • Tax Reporting of Cryptocurrency and Current Enforcement Trends, Strafford, 1.19.2023
    • Civil Tax Workshop: It’s a World of Depositions: Discovery in the Tax Court and the Federal District Courts, ABA’s 2022 National Institute on Criminal Tax Fraud and Tax Controversy, 12.12.2022
    • Keeping Your Clients Out of Hot Water: Drafting Effective Tax Return Disclosures, UT Law Annual Taxation Conference, 12.1.2022
    • Avoiding IRS Challenges to Your Client’s Estate Plan, New England IRS Representation Conference, 11.18.2022
    • Technology’s Impact on Criminal Tax Enforcement: IRS Cybercrimes 2022, Federal Bar Association’s Annual Tax Law Conference, 3.4.2022
    • Cryptocurrency: Where Are We Today?, ABA’s 2021 National Institute on Criminal Tax Fraud and Tax Controversy, 12.10.2021
    • Foreign Forms 101: The Forms Every Practitioner Should be Familiar With, New England IRS Representation Conference, 11.18.2021
    • Exploring Careers in Tax Law, Morehouse/Spelman Pre-Law Society, 4.15.2021
    • Cannabis Is Going National: Opportunities and Pitfalls, Federal Bar Association’s Annual Tax Law Conference, 3.5.2021
    • Cryptocurrency: Current Tax and Bank Secrecy Act Regulatory and Enforcement Environment, Celesq, 2.26.2021
    • Tax Collection in the Time of COVID-19, ABA Section of Taxation, 4.9.2020
    • The Age of Promoter Penalties: Fighting the Good Fight, ABA Section of Taxation’s 2020 Midyear Meeting, 2.1.2020
    • Collection of Foreign Tax Judgments: When Your Other Problems Come Home, ABA Section of Taxation’s 2020 Midyear Meeting, 1.31.2020

Speaking engagements listed are 2020 – present.*

Publications*

  • Articles*
    • Coming Clean: The Benefits and Limits of the Tax Division’s New Corporate Voluntary Self-Disclosure Policy, Journal of Tax Practice & Procedure, 7.1.2023
    • Using Disclosure Statements to Proactively Manage Tax Controversies, Journal of Tax Practice & Procedure, 12.21.2022
    • Correcting Employment Tax Noncompliance, Journal of Tax Practice & Procedure, 10.1.2022
    • Answers to your Burning R&E Expenditure and R&D Tax Credit Questions, Bloomberg Law, Tax Management Memorandum, 8.1.2022
    • Is New Jersey’s Indefinite Extension for Tax Assessments Constitutional?, Tax Notes State, 5.27.2022
    • Tax Reporting Requirements for Disregarded Entities with International Activities, Bloomberg Law, Tax Management Memorandum, 4.11.2022
    • The Significant, Yet Often Ignored, Tax Consequences of Moving Out of New York and the U.S., New York Law Journal, 2.3.2022
    • Promoting Diversity, Inclusion, And Equality Through Pro Bono Service, Tax Notes State, 4.5.2021
    • PENALTIES—Reconsidering the Reasonable Cause Defense to Late-Filing Penalties and the Impact of the Service’s Clarification of the DIIRSP, Journal of Tax Practice & Procedure, 2.8.2021
    • Mitigating IRS Cryptocurrency Enforcement Risk in 2021, Law360, 1.4.2021
    • Taxpayers That Paid the Net Investment Income Tax or the Additional Medicare Tax Should Consider Filing Protective Claims for Refund, Westlaw Journal, 8.17.2020
    • Penalties Against, and Investigations of, Tax Return Preparers, Promoters, and Appraisers, TAXES – The Tax Magazine, 5.1.2020

Articles listed are 2020 – present.*

  • Books*
    • 621-4th, IRS National Office Procedures – Rulings, Closing Agreements, BNA Portfolio, 1.15.2023
    • 645-3d, Innocent Spouse Relief, BNA Portfolio, 3.1.2022
    • Effectively Representing Your Client Before the IRS – Chapter 10, ABA Section of Taxation, 10.6.2021

Books listed are 2020 – present.*

Education

  • J.D., University of Florida College of Law, 2006

    LL.M., Taxation, Georgetown University Law Center, 2010

    M.B.A., Finance, Binghamton University, 2003

    B.A., Political Science, Binghamton University, 2001

Admissions

  • New Jersey

    New York

    District of Columbia

Courts

  • U.S. Court of Appeals for the Second, Third, Fourth, Eleventh and DC Circuits

    U.S. Court of Federal Claims

    U.S. District Court for the District of New Jersey

    U.S. District Court for the Eastern and Southern Districts of New York

    U.S. Tax Court

Clerkships

  • The Hon. David Laro, U.S. Tax Court, 2010-2012