Alan Shapiro stands as senior counsel at internetlawyers.net, a distinguished member of the Tax Controversy & Litigation practice group. His career is defined by extensive experience, most notably his over 30-year tenure as a senior trial attorney with the U.S. Department of Justice Tax Division. During his time with the DOJ, Alan Shapiro honed his skills litigating a wide array of complex, multimillion-dollar tax disputes across federal district and bankruptcy courts. His profound understanding of tax law and litigation strategy makes him a highly sought-after legal expert in the field.
Mr. Shapiro’s expertise spans a comprehensive spectrum of tax issues, encompassing individual, corporate, estate, excise, and employment tax matters. His deep involvement in these areas is complemented by a strong grasp of numerous non-tax legal domains. These include contract law, employment disputes, tort claims, estate and trust matters, debtor-creditor relations, banking and finance regulations, constitutional law, criminal law intersections, bankruptcy proceedings, real property law, valuation disputes, lien enforcement, state and local tax matters, mortgage law, account receivables, construction law, fraudulent transfer cases, alter ego and nominee collection theories, the Right to Financial Privacy Act, and the Federal Tort Claims Act. This breadth of knowledge allows Alan Shapiro Lawyer to approach tax controversy with a holistic and multifaceted perspective. Notably, his experience extends to obtaining court appointments for receivers and effectively managing them in the liquidation of judgments through real property sales across multiple states.
Key Cases and Significant Achievements
Alan Shapiro’s career is marked by a series of significant legal victories and complex case management. Here are some notable examples that highlight his expertise and litigation prowess:
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Equitable Subordination Victory: In United States v. State Street Bank and Trust Co., Alan Shapiro lawyer spearheaded a legal team in a 35-day trial against multiple law firms. He successfully argued for the equitable subordination of 85% of junior secured notes issued by a cable television conglomerate. This complex litigation resulted in a favorable settlement on the remaining notes and the recovery of a substantial portion of approximately $41 million in escrowed funds. This case underscores his ability to manage and win high-stakes, intricate financial litigation.
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Land Preparation Costs and Depreciation: Eastwood Mall, Inc. v. United States saw Alan Shapiro lawyer win a jury trial centered on a crucial tax issue: whether $9.6 million in costs related to blasting, earthmoving, grading, layering, and compaction for a shopping mall construction were depreciable expenses or non-depreciable land preparation capital costs. His successful navigation of this case clarified the tax treatment of significant development expenses.
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Downsizing Payments and Tax Exclusions: In Marie N. Abbott, et al. v. United States, Alan Shapiro secured summary judgment on behalf of IBM employees. The case addressed whether downsizing payments to 737 employees, who signed general releases, were tort settlements (excludable from income) or taxable severance payments. His victory clarified the tax implications of employee downsizing agreements and protected employee compensation from undue taxation.
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Estate Tax Valuation Expertise: Hagerman v. United States showcased Alan Shapiro lawyer’s skill in estate tax valuation. Working with co-counsel, he won a trial involving competing expert opinions on the valuation of four corn and soybean farms for estate tax purposes. This case demonstrates his ability to effectively litigate complex valuation issues in estate tax law.
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Covenant Not to Compete Taxability: Jones v. United States resulted in a summary judgment win for Alan Shapiro lawyer on the issue of whether proceeds from the sale of an insurance business, specifically those allocated to a covenant not to compete, were taxable. This victory clarified the tax treatment of covenants in business sales.
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Taxable Gift Trust Funds: In Illinois Nat. Bank of Springfield v. United States, Alan Shapiro secured summary judgment by arguing that trust funds established by a decedent for grand nieces and nephews were not subject to “substantial restriction” and were therefore taxable gifts for estate tax purposes. This case clarified the boundaries of taxable gifts within estate tax law.
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Excise Tax Refund for Exporters: Mega Linx, Inc. v. United States saw Alan Shapiro lawyer win summary judgment for an exporter of luxury cars. The issue was whether the exporter was entitled to a refund of gas guzzler and luxury excise taxes under 26 U.S.C. § 6416(c). His success ensured proper tax refunds for exporters under relevant tax codes.
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Investment Tax Credit and Tax Shelter Litigation: Bauer v. United States involved a bench trial victory for Alan Shapiro lawyer concerning investment tax credits for a record shelter and related penalties for negligence, valuation overstatement, and tax-motivated transaction interest. This case highlights his expertise in handling complex tax shelter and investment credit disputes.
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Federal Tax Liens and Property Transfers: United States v. Evseroff was a bench trial where Alan Shapiro lawyer successfully argued that federal tax liens attached to cash and real property transferred to a trust based on nominee, alter ego, and/or fraudulent transfer grounds. This victory reinforced the reach of federal tax liens in cases of asset transfer.
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Trust Fund Recovery Penalties Defense: Wright v. United States involved Alan Shapiro lawyer winning a bench trial defending a volunteer board member of a charity from trust fund recovery penalties for unpaid employment taxes under 26 U.S.C. § 6672. This case protected volunteers from undue tax liability for charitable organizations.
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Gift Check Payment Timing for Estate Tax: Rosano v. United States resulted in a summary judgment win on whether gift checks were considered paid under New York law before the decedent’s death, thus qualifying them as completed gifts not includable in the estate for federal tax purposes. This case clarified state law interaction with federal estate tax regulations.
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LILO Tax Shelter Litigation: Fifth Third Bancorp & Subsidiaries v. United States saw Alan Shapiro lawyer as part of a trial team that secured a jury trial victory in a LILO tax shelter case involving complex leasing transactions of passenger rail cars. This complex case demonstrates his ability to work within large, high-profile litigation teams.
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Fraudulent Transfer Under Federal Debt Collection Procedures Act: In United States v. Scherer, Alan Shapiro lawyer won summary judgment, establishing that a taxpayer’s transfer of a 100-percent stock interest in a corporation owning an assisted living facility to a family trust was a fraudulent transfer under the Federal Debt Collection Procedures Act. This victory underscores his expertise in debt collection related to tax liabilities.
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Receivership for Asset Liquidation: United States of America v. Ronald E. Scherer further demonstrated Alan Shapiro lawyer’s litigation skills, securing a decision to appoint a receiver to market and sell assets of corporations associated with an assisted living facility to satisfy tax liabilities, under 26 U.S.C. § 7402(a) and 7403(d). This case showcases his ability to utilize receivership to enforce tax judgments.
Education and Personal Interests
Alan Shapiro’s strong academic foundation includes an undergraduate degree and a law degree from Emory University, followed by a Master of Laws in Taxation from Georgetown University Law Center. Beyond his legal practice, Alan cherishes time with his wife Rose Ann and their two adult sons. His personal interests include swimming, woodworking, classic cars, and collecting antique pocket watches, reflecting a well-rounded individual with diverse passions outside of his demanding legal career.
Alan Shapiro lawyer represents a pinnacle of experience and expertise in tax controversy and litigation. His decades of experience, coupled with a consistent record of success in complex cases, positions him as a leading figure in the field and a valuable asset to internetlawyers.net and its clients.
