icon on “I approach the practice of law as both a legal counselor and strategic business advisor, helping clients navigate complex transactions, manage risk, and make informed decisions that advance their commercial objectives and position them for long-term success.”
Reginald Guy II is an accomplished corporate and transactional attorney with extensive experience advising businesses, executives, investors, and entrepreneurs on complex legal, commercial, and strategic matters. Drawing on his extensive experience in both private practice and corporate legal leadership, Reginald brings a business-minded, solutions-oriented approach to legal counseling. He serves as a trusted strategic advisor, helping clients navigate sophisticated transactions, manage risk, capitalize on business opportunities, and make informed decisions that advance their immediate objectives and long-term growth.
Reginald's practice focuses on mergers and acquisitions, private equity, venture capital, corporate governance, complex commercial agreements, strategic partnerships, technology transactions, data privacy, and general corporate counseling. He has represented established corporations, private equity sponsors, investors, and emerging businesses in multimillion-dollar acquisitions, divestitures, investments, and other significant commercial transactions. Reginald works closely with business owners, executive leadership, boards of directors, and in-house legal teams to structure and execute transactions, address operational challenges, and develop practical legal strategies aligned with broader business objectives.
Prior to joining Howard & Howard, Reginald served as Deputy General Counsel and Corporate Counsel, advising senior leadership on strategic business initiatives, commercial transactions, regulatory compliance, corporate governance, and enterprise risk management. His background also includes serving as a partner in private practice and practicing at nationally recognized law firms, where he counseled clients on sophisticated corporate transactions and business matters. This combination of in-house and private practice experience enables Reginald to approach legal issues with a comprehensive understanding of both the legal complexities and commercial considerations that influence business decisions.
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Business & Corporate
Our business is business–your business. We offer vast experience in a full array of corporate legal services.
Credentials
Education
- Northwestern University Pritzker School of Law, 2016
- J.D.
- Howard University, 2008
- B.B.A, Marketing
Memberships
- Cook County Bar Association
- Association Corporate Counsel
- American Bar Association
- Chicago Bar Association
Admissions
- Illinois, 2016
Professional Achievements
- Illinois Super Lawyers, "Rising Stars," 2024
- Greenberg Traurig 2019 Corporate Associate Pro Bono MVP
Community
Community“I believe meaningful leadership extends beyond the practice of law. I am deeply committed to serving and strengthening Chicago's communities through civic engagement, mentorship, education, and philanthropy. My involvement with organizations focused on youth development, educational opportunity, professional advancement, and community empowerment reflects my belief that success carries a responsibility to create opportunities and make a lasting difference in the lives of others.”
Reginald is a dedicated civic leader and community advocate with an extensive record of service throughout Chicago, particularly on the city's South Side. His commitment to mentorship, education, economic empowerment, and community development is reflected in his leadership and board service with numerous professional, educational, and nonprofit organizations.
Reginald serves on the Boards of Directors of the South Side YMCA and the Black Men Lawyers' Association, where he supports initiatives promoting youth development, professional advancement, and mentorship. He also serves as a Community Representative on the Local School Council of Robert A. Black Magnet School, his former elementary school, advocating for educational excellence, student achievement, and meaningful community engagement.
As Volunteer Operations Director of the Woodlawn Greater Food Pantry, Reginald has helped lead efforts to combat food insecurity and expand access to essential resources for individuals and families throughout Chicago's South Side. He also serves as Board Treasurer of the Johnathan W. Buckner Youth Initiative, where he provides financial oversight and supports the organization's mission of empowering young people through education, mentorship, career development, and enrichment opportunities.
Reginald is an active member and former chapter officer of Kappa Alpha Psi Fraternity, Incorporated, through which he has helped organize and lead community service initiatives, youth mentorship programs, scholarship efforts, and charitable events. He is also a past president of the Howard University Alumni Club of Chicago and serves on Northwestern University Pritzker School of Law's Young Alumni Council.
Through these commitments, Reginald continues to leverage his professional experience, leadership, and relationships to strengthen communities, expand educational and economic opportunities, and develop the next generation of leaders.