George Washington University Law School, J.D., 2012

George Washington University School of Business, B.B.A., International Business and Finance, 2006




American College of Investment Counsel

George Washington University Law School Business and Finance Advisory Council


Chicago Humanities Festival Board of Directors 

Executive Board of SPARK–Chicago

Charles Calloway is an associate in Chapman and Cutler’s Corporate Finance Department. He participated in the firm’s summer associate program in 2011 and joined the firm in 2012.

Charles’s practice includes representation of financial institutions and other businesses in connection with domestic and international direct placements of senior and subordinated debt in secured and unsecured financings including real estate, public utilities, sports finance, and general corporate financings. In these recent financings, issuers and guarantors and entities providing credit support included domestic entities as well as entities from Australia, Canada, Germany, Ireland, Japan, Luxembourg, the Netherlands, Poland, South Africa, Switzerland, the United Kingdom. Investors included entities from the United States, Canada, Ireland, Australia, and the United Kingdom.

Prior to law school, Charles worked as a financial consultant and then helped found the government relations branch of Calloway & Associates, Inc., which delivered financial management services, information technology solutions, and logistics management to federal, state and local government clients.

During law school, Charles worked as a judicial intern for the honorable Wendell P. Gardner Jr. researching criminal issues, writing legal memoranda, and drafting case briefs. He also worked on the Innocence Project in New Orleans, providing legal representation to the wrongfully convicted of Louisiana and Mississippi serving sentences over 10 years.

Representative Transactions

  • Represented institutional investors in purchasing in excess of $450 million senior term notes of the Major League Baseball Trust as part of a structured finance program established by Major League Baseball to facilitate the financing of member clubs
  • Represented investors in the purchasing in excess of $400 million in trust certificates backed by both NFL league-wide revenues
  • Represented investors in the purchasing in excess of $500 million senior notes of the various NFL teams backed by the stadium and team assets
  • Represented investors in the purchase of debt securities collateralized by MLB stadium revenues
  • Represented institutional investors in more than 30 transactions involving the purchase of senior notes and mandatory redeemable preferred shares of various 1940 Act investment company closed end funds


  • Moderator, “What’s New with the Securities Valuation Office of the NAIC,” 2017 American College of Investment Counsel’s Fall Meeting and Education Conference. October 19–20, 2017.

Honors & Awards

  • Recipient of Chapman and Cutler's 2013 Pro Bono and Volunteer Achievement Award, honoring his work with Spark Chicago
  • Chapman and Cutler's Pro Bono Honor Roll