JACK PIROZZOLO focuses his practice on government facing and government adjacent litigation. His matters cross the spectrum of criminal and regulatory enforcement litigation, with a particular emphasis on heavily regulated industries, such as healthcare, life sciences, energy, and financial services. Since his arrival at Sidley in 2014, Jack has successfully represented companies and individuals being investigated by or charged by U.S. Attorneys’ Offices, the U.S. Department of Justice, the Securities and Exchange Commission, the U.S. Department of Labor, the Massachusetts Attorney General’s Office, the New York Attorney General’s Office, the New York Department of Financial Services, and various other state and federal agencies. As lead counsel, he has handled and is currently handling several high profile matters in various courts around the country and has secured dismissals and declinations in several matters while at Sidley. Although primarily a courtroom lawyer, Jack has also conducted several internal investigations and routinely provides compliance advice to his clients. Jack leads Sidley’s pro bono efforts in Boston.
Jack joined Sidley after a 10-year career in the U.S. Attorney’s Office for the District of Massachusetts, the last five years of which he served as the First Assistant U.S. Attorney.
Jack has been recognized by The Best Lawyers in America® in the areas of Litigation — Regulatory Enforcement (SEC, Telecom, Energy) and Commercial Litigation (2017–2024) and as a “Lawyer of the Year” in Litigation - Regulatory Enforcement (SEC, Telecom, and Energy) in Boston (2018 and 2024). In 2022, Jack was recognized as a “Go To Lawyers: Business Litigation” by Massachusetts Lawyers Weekly. Jack is also a member of the American Law Institute.
Jack received his undergraduate degree from Yale University. He attended the University of Chicago Law School, where he was comment editor of the University of Chicago Law Review, graduated with honors and was elected to the Order of the Coif. Jack clerked for both Judge Sandra L. Lynch on the First Circuit and Judge Edward R. Becker on the Third Circuit.
- Healthcare and life sciences. Jack has represented, and is currently representing and advising, pharmaceutical and medical device companies, insurers, institutional healthcare providers and other organizations and individuals in the healthcare industry in a variety of matters. These matters involve a range of regulatory and legal issues, including the False Claims Act, current good manufacturing practices (cGMP), the Anti-Kickback Statute, pricing and reimbursement, patient assistance programs, Massachusetts consumer protection laws and product safety.
- Securities. Jack has represented, and is currently representing and advising, asset managers, broker-dealers and issuers in connection with investigations that implicate a range of issues under the securities laws, including the 1933 Act, the 1934 Act, the Investment Company and Investment Adviser Acts of 1940, federal fraud statutes, FINRA rules and state securities laws. Jack has experience representing companies in the blockchain industry before the SEC. Jack also recently represented a multi-billion dollar asset manager in an SEC insider trading enforcement investigation that resulted in the SEC declining the matter.
- Other Enforcement Matters. Jack has represented, and is currently representing and advising, individuals and organizations in connection with other types of federal investigations and prosecutions, involving, for example, tax issues, daily fantasy sports and college admissions.
- Litigation. Since joining Sidley, Jack has handled several multi-million dollar matters before federal and state courts, including, for example, CEI Enterprises, Inc., et al. v. Anchin, Block and Anchin LLP, Nos. 09-cv-11708 (D. Mass.) and 15-1858 (First Circuit) (representation of accounting firm in breach of fiduciary duty and malpractice claim brought by author Patricia Cornwell; secured judgment vacating jury award of $50 million and ordering dismissal in part and new trial in part); William and Patricia Cavallaro v. Commissioner of Internal Revenue, Nos. 15-1368, 15-1376 (First Circuit) (representation of taxpayers in $50 million gift tax dispute; secured remand to Tax Court and currently representing taxpayers before the U.S. Tax Court) (ongoing).
- Pro Bono. Jack leads Sidley’s pro bono efforts in Boston. Among other pro bono matters, Jack assists public charities and foundations with internal investigations and compliance efforts. He also represents individuals seeking asylum on federal appeals.
Jack’s prior experience includes:
Before joining Sidley, Jack, as First Assistant, was a principal litigator for the United States in the District of Massachusetts overseeing more than 120 assistant U.S. attorneys in both the criminal and civil divisions and hundreds of criminal and civil matters handled by the U.S. Attorney’s Office, including matters of national and international significance, such as the nation’s largest ever healthcare fraud prosecution and settlement, the apprehension and prosecution of James J. “Whitey” Bulger, and the apprehension and, until Jack’s departure from the office in 2014, the prosecution of the Boston Marathon Bombing defendant, Dzhokhar Tsarnaev. In addition to those three matters, Jack:
- oversaw a US$950 million civil and criminal resolution with a large pharmaceutical company;
- served as acting U.S. attorney on a successful undercover operation and subsequent prosecution of an individual planning a terrorist attack on the Pentagon;
- served as a commissioner, enforcing an international subpoena request from the United Kingdom seeking materials held at Boston College and related to the conflict in Northern Ireland; and
- served as the lead prosecutor in the investigation and prosecution of James Bulger’s longtime girlfriend, Catherine Greig.
As an Assistant U.S. Attorney in the Economic Crimes Unit, Jack investigated and prosecuted various white collar offenses, including securities and accounting fraud matters, tax crimes and mail, wire and bank fraud offenses. He tried cases involving, among other things, public securities markets fraud, Ponzi scheme and tax frauds. In 2006 and 2007, Jack won awards from both the Department of Justice and the U.S. Postal Inspection Service for his work on a series of mutual fund trading abuse cases, which, among other things, resulted in the convictions of several individuals and a US$600 million corporate resolution.
Jack also handled several matters before the U.S. Court of Appeals for the First Circuit both as First Assistant and as an Assistant U.S. Attorney.
Prior to joining the U.S. Attorney’s Office, Jack was a partner at a Boston-based law firm where, among other things, he focused on defending accountants and auditors in securities class actions.