Shemario O. Winfrey

Shemario Winfrey Headshot


Shemario Winfrey is a business attorney in Holland & Knight's Chicago office, where he focuses his practice on a variety of corporate transactions.

Mr. Winfrey represents public and privately held companies with respect to mergers and acquisitions (M&A), corporate formation, and governance and compliance. He also has extensive experience in the transportation and energy industries, with a particular focus on regulatory compliance.

Before his promotion to associate, Mr. Winfrey interned as a law clerk in Holland & Knight's Chicago office.

Prior to attending law school and throughout the course of his studies, Mr. Winfrey served as director of transportation projects and systems for Phillips 66 Co. in Houston and director of corporate compliance for Hub Group Corp. in Oak Brook, Illinois. In these positions, Mr. Winfrey was responsible for, among other things, managing corporate regulatory programs related to Federal Railroad Administration (FRA), Federal Motor Carrier Safety Administration (FMCSA), and Pipeline and Hazardous Materials Safety Administration (PHMSA) compliance. He also served as a member of rail safety working groups of the various oil and gas trade associations.


  • Loyola University Chicago School of Law, J.D.
  • Loyola University Chicago School of Law, M.J., Business and Corporate Governance Law
  • Georgia State University, B.B.A., Operations Management
Bar Admissions/Licenses
  • Georgia
  • Illinois
  • Iowa
Court Admissions
  • Supreme Court of Iowa
  • Iowa Court of Appeals
  • All U.S. District Courts in Iowa
  • American Bar Association
  • National Bar Association
  • The Iowa State Bar Association
  • The Iowa State Bar Association, Young Lawyers Division
Honors & Awards
  • Holland & Knight Pro Bono All-Star, 2020
Spoken Languages
  • English
  • German