Jay represents individuals and entities facing investigations and prosecutions by the IRS, the FBI, state investigative agencies, U.S. Attorney’s offices, and the Department of Justice Tax Division. His clients rely on his ability to analyze cases from the government’s perspective and trust his sound judgment to guide them through their most difficult challenges.
Jay has defended clients against federal investigations and charges throughout the country. He regularly handles matters involving allegations of offshore tax evasion, employment tax violations, cryptocurrency reporting violations, use of shell companies, currency reporting violations, and underreporting of business income. He also has substantial experience representing clients accused of promoting or participating in so-called tax shelters, including captive insurance programs, conservation easements, and Puerto Rico’s Act 20/Act 22 program. In many instances, Jay represents tax professionals facing such accusations.
Jay spent more than a decade as both a federal and a state prosecutor. At the Department of Justice’s Tax Division, he supervised more than 30 federal tax prosecutors and oversaw criminal tax enforcement for a region covering 22 states. He investigated and prosecuted, among many other tax offenses, an e-commerce tax fraud scheme, a thoroughbred race horse tax fraud scheme, an abusive trust scheme, and numerous individuals and businesses engaged in tax evasion. In addition to the cases that he prosecuted, he was also responsible for reviewing and authorizing criminal tax grand jury investigations and prosecutions in the various U.S. Attorney’s Offices in his 22-state region. He is a veteran trial lawyer, having conducted dozens of jury trials and hundreds of bench trials.
Jay is a member of the ABA’s Section of Taxation, Civil and Criminal Tax Penalties Committee, as well as of the ABA’s Criminal Justice Section, White Collar Crime Committee, and a member of the Edward Bennett Williams Inn of Court.
From 2013 to 2016, Jay assisted the White House Office of Presidential Personnel in a pro bono capacity by vetting potential presidential appointees for possible tax-related problems.