Charles focuses his practice on representing financial institutions and strategic investors in corporate, project, ESG, and structured finance transactions (domestic and cross-border). He has broad experience in private placements of debt and equity securities representing insurance companies, finance companies, and institutional investors. He also advises financial institutions on secured and unsecured financings across various sectors, including REITs, public utilities, private equity funds, venture capital, project finance, hedge funds, and general corporate financings. Additionally, Charles has robust experience representing lenders in secured and unsecured credit facilities to private equity funds and their portfolio companies.
Charles also has experience in mergers and acquisitions, having advised companies on growth investments and strategic investors on various types of acquisition financings.
In addition to his finance practice, Charles maintains an active sports finance practice. He has represented strategic investors in league-wide financings for the National Football League (NFL) and Major League Baseball (MLB). He has also represented strategic investors in a number of high-profile stadium financings in the United States, such as TD Boston Garden, Mercedes-Benz Atlanta Falcons Stadium, Lincoln Financial Field, and Las Vegas Raiders Allegiant Stadium.
Concentrations
• Corporate finance and securities
• Domestic and cross-border institutional private placements
• Energy and infrastructure finance
• LP/GP lending programs
• M&A
• Private equity
• Project finance
• Sports finance
Experience
Cross-Border and Domestic Private Placement Representative Transactions
• Represented institutional investors in more than 75 transactions involving the purchase of senior notes and mandatory redeemable preferred shares of various 1940 Act investment company closed-end funds.°
• Represented institutional investors in private placement transactions totaling approximately over $8 billion of senior notes issued to major real estate development companies around the world.°
• Represented investors in the purchase of €360 million unsecured notes a multinational materials company based in Belgium.°
• Represented institutional investors in connection with the purchase of £2 billion of senior notes of an Austrian multinational alimentation chain.°
• Represented institutional investors in connection with the purchase of £200 million of senior notes of a British multinational hotel and restaurant company.°
• Represented institutional investors in connection with the purchase of $360 million of senior notes of a leading U.S.-based heavy sour crude refining company.°
• Represented institutional investors in connection with the purchase of £280 million of guaranteed unsecured notes of a UK-based property estate.°
• Represented institutional investors in connection with the purchase of €142.5 million senior notes of a U.S.-based leading manufacturer of household cleaning supplies and other chemicals.°
• Represented institutional investors in connection with the purchase of senior secured notes of an Australian-based global markets leader in plastic solutions and masterbatches.°
• Represented institutional investors in connection with the purchase of first mortgage bonds of large Alaska-based natural gas and hydroelectric plant utility company.°
• Represented institutional investors in connection with the purchase of unsecured senior notes of a Texas-based operator of transmission and distribution facilities.°
• Represented institutional investors in multiple restructuring and forbearance agreements including engagement of financial advisors, addition of collateral guarantees, multi-party collateral agency agreement, note exchange, and eventual pay off at full make-whole amount.°
• Represented institutional investors in connection with the purchase of unsecured notes of a UK-based multinational automotive distribution, retail, and services company.°
• Represented institutional investors in connection with the purchase of $250 million secured notes of a multi-state transmission utility based in Wisconsin, Michigan, Minnesota, and Illinois.°
• Represented institutional investors in connection with short-term waiver and ultimate pay off at make-whole amount.°
• Represented institutional investors in connection with the purchase of senior notes of a UK-based property investment and development company.°
• Represented institutional investors in connection with the purchase of $405 million of unsecured senior notes of a France-based international pharmaceutical group.°
• Represented institutional investors in the purchase of $350 million secured notes of a large transmission and electricity distribution company.°
• Represented institutional investors in the purchase of $232 million secured notes of a Canadian asset manager used to finance the acquisition of domestic and cross-border wireless telecommunication assets and renewable energy assets.°
Project Finance / ESG
• Counsel to institutional investors in connection with the issuance by a top 10 publicly traded ESG investor of approximately $100 million of investment-grade senior notes secured by the ESG investor’s cash flowing membership interests in holdco entities owning over 600 separate behind-the-meter community and C&I solar and storage projects housed in 13 different states.°
M&A
• Served as U.S. legal counsel to Austrian technology company PSPDFKit in the company’s first growth investment. PSPDFKit provides software employed by thousands of companies, organizations, governments, and developers to power document processing and productivity tools, serving nearly one billion end-users in over 150 countries. The company announced a more than €100 million growth investment from investor Insight Partners, a global venture capital and private equity firm.°
Bank Lending
• Counsel to bank lenders in over 50 GP and LP programs for private equity funds.
• Counsel to bank lenders in revolving letters of credit, credit agreements, RLOCs, and NAV Loans.
Sports League and Team Representative Transactions
• Represented institutional investors in purchasing in excess of approximately $2 billion in senior term notes of the Major League Baseball Trust as part of a structured finance program established by MLB to facilitate the financing of member clubs.°
• Represented investors in the purchase of numerous issuances of debt securities collateralized by MLB stadium revenues.°
• Represented investors in the purchase of secured notes in connection with refinancing NFL stadium financings.°
• Represented investors in the purchase of senior notes of the various NFL teams backed by the stadium and team assets.°
• Represented investors in the purchase in excess of approximately $3.5 billion in trust certificates backed by NFL league-wide revenues.°
°The above representations were handled by Mr. Calloway prior to his joining Greenberg Traurig, LLP.
Internships
• Judicial Intern, Hon. Wendell P. Gardner, Jr., The Superior Court of the District of Columbia, 2010
• Summer Intern, Innocence Project – New Orleans, 2010
Recognition & Leadership
Awards & Accolades
• Listed, Diversity MBA magazine, “Top 100 Under 50 Executive Leaders,” 2024
• Listed, Crain’s Chicago Business, “40 Under 40,” 2023
• Recipient, Cook County Bar Association, “Next Generation” Award, 2023
• Listed, Crain’s Chicago Business, “Notable Nonprofit Board Leader,” 2021
Professional & Community Involvement
• American College of Investment Counsel (ACIC)
o Member, Board of Trustees, 2022-Present
o Co-Chair, Transition Process Management Committee, 2022-Present
o Co-Chair, Website Committee, 2024-Present
o Co-Editor, Private Notes, 2019-2022
• Member, Business Leadership Council, 2022-Present
• Member, Economic Club of Chicago, 2022-Present
• The George Washington University Law School
o Member, Dean’s Advisory Council, 2022-Present
o Member, Business and Finance Advisory Counsel, 2018-Present
• Member, Advisory Board, After School Matters, 2024-Present
• Member, Board of Directors, Black Ensemble Theater, 2023-Present
• Chicago Humanities Festival
o Member, Board of Directors, 2017-Present
o Chair and Treasurer, Audit, Finance, and Investment Committee, 2021-Present
• Member, Host Committee, 2026 Presidents Cup
• Member, Executives Club of Chicago, 2020-Present
• Fellow, Leadership Greater Chicago Signature Fellows Program, 2022
• Fellow, University of Chicago Booth School of Business, Chicago Urban League Impact Leadership Program, 2021
