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Member

Leonard L. Fleisig

Leonard L. Fleisig

Credentials

Credentials

Education

  • J.D., New York University, 1990
  • B.A., University of Manchester, 1975

Involvement

  • Hampton Roads Global Business Council, President (2014/2015)
  • Virginia Maritime Association, Shippers Committee (2013/2014)
  • Hampton Road CIVIC (2013)
  • Maritime Administrative Bar Association: Secretary-Treasurer (1999-2000); Vice President (2000-2001); President (2001-2002)
  • Maritime Law Association: Carriage of Goods Committee; Electronic Commerce Committee
  • CIVIC Leadership Institute, Board Member
  • Tidewater Wooden Boat Workshop, Board Member
  • VersAbility Resources, Business Advisory Committee
  • CIVIC Leadership Institute, Board Member Emeritus
  • Virginia Maritime Association, Logistics/Customs Committee
  • Hampton Roads Global Business Council, President Emeritus

Admissions - Bar

  • New York
  • District of Columbia
  • Virginia

Maritime and Trade Counsel With Deep Logistics Experience

A partner in our Maritime and International Trade & Commerce groups, Len pairs twelve years in logistics between college and law school—moving hundreds of containers weekly across the U.S., Europe, Africa, and Asia—with seasoned advocacy to deliver business-savvy counsel. He guides clients through export and import compliance before the United States Customs and Border Protection (CBP), the Department of Commerce’s Bureau of Industry and Security (BIS), the Department of the Treasury’s Office of Foreign Assets Control (OFAC), and the Department of State’s Directorate of Defense Trade Controls (DDTC). From proactive planning to high-stakes enforcement, Len turns complex cross-border issues into practical action on classification, licensing, sanctions, and disputes. Clients value Len’s clear-eyed, responsive approach that keeps business moving.

Notable Work & Achievements

United States Customs and Border Protection

Leonard represents Canadian oil, gas, and electricity corporations in navigating the complex web of customs and trade regulations put in place between the U.S. and Canada in 2025.

In the same vein, Len is providing ongoing advice to a multinational apparel company’s e-tailing operations regarding tariff and supply chain challenges that pose exposure to great costs and risks in our new tariff environment.

Len continues to advise multiple divisions of an overseas headquartered multinational manufacturing corporation on matters relating to the new world of tariffs, with an increasing focus on measures that can be lawfully put into place to mitigate the client’s exposure to increased rates of duty.

He also represents multiple large and small clients in enforcement proceedings initiated by U.S. Customs and Border Protection and has s Successfully mitigated or reduced threatened fines and penalties in all such enforcement proceeding.

When a foreign manufacturer needed a valuation and pricing structure that would work in the real world. Len mapped a corporate model for its United States manufacturing and distribution arm that maximized compliance with both tax and customs regulations, which often create conflicting standards so the business could create a viable pricing structure to avoid those conflicts.

Len stood for a multinational energy client at the Court of International Trade, where the question was simple but sweeping: whether natural gas entering by pipeline qualified under the North American Free Trade Agreement. He built the record, framed the business impact, and drove a result that aligned trade rules with real-world operations.

Classification disputes can stall supply chains and cash flow. Len represented a European company in the Court of International Trade, secured a settlement confirming the correct tariff classification, and delivered a refund exceeding $1,000,000.

A client came forward with a significant potential breach of United States security regulations. Len guided a voluntary prior disclosure to United States Customs and Border Protection that earned a warning letter—no fine, no penalty.

Getting the rules right up front prevents problems later. Len has obtained formal rulings on classification, valuation, and country-of-origin marking for a range of imported goods, giving clients certainty they could rely on in procurement, pricing, and planning.

Export

Len advises multiple clients in all aspects of export trade controls relating to the export of military items (DDTC), dual-use items (BIS) and to the impact of U.S. and EU sanctions policies on shipments destined for sanctioned countries (OFAC).

He provides export classification services for shippers seeking to export dual-use or military products and represent clients in filing voluntary disclosures arising out of their export transactions.

Bureau of Industry and Security

For a global pharmaceutical manufacturer, Len provided substantial advice and counsel with regard to export controls and sanctions. In other matters, Len managed voluntary disclosures, rebuilt compliance programs, and reset relationships with regulators.

Department of State

Defense contracting raises unique control issues. Len helped a United States software and solutions provider design the right internal guardrails and, when needed, secured Technical Assistance Agreements from the United States Department of State—so teams could collaborate lawfully and deliver on mission.

Office of Foreign Assets Control

Sanctions programs shift, but business cannot stand still. Len has advised domestic and foreign clients on transactions and risk involving Cuba, North Korea, Libya, and Iraq—translating complex restrictions into clear, operational guidelines.

Litigation

And when disputes escalate, Len goes to court. Len has litigated in United States District Courts and Courts of Appeals for importers, transportation companies and logistics providers— with briefs built on commercial reality, legal arguments shaped for maximum effectiveness order to achieve results that keep goods, and companies, moving.

Recognitions

  • Virginia's "Legal Elite," Virginia Business magazine (2015-2023), Administrative Government

What does Structured for Solutions mean to you and how do you apply that to your work?

Advising concerned and anxious clients with regard to import tariffs and trade matters provides unique challenges. That is why my mantra remains, as it has from the beginning of my practice: know your client, know your client’s business, know the law; and provide advice and counsel in a measured, empathetic manner designed to provide a measure of calm in a sea of global supply chain uncertainty.