“Bob and Bennett embody the excellence, judgment, and leadership that define Shumaker’s nationally recognized sports law practice,” said Jennie Compton, Shumaker’s Managing Partner and Chair of the Management Committee.
TOLEDO, OH — Shumaker Partners Bob Boland and Bennett Speyer have been named to the 2026 Lawdragon 500 Leading Global Entertainment, Sports & Media Lawyers, recognizing their professional excellence and results in high-stakes matters, industry leadership, innovation, and influence in sports law.
Bob was recognized for Litigation & Compliance in Sports, and Bennett was recognized for Disputes & Investigations in Sports. Both are widely regarded as leaders within Shumaker and serve as Co-Chairs of the Hospitality, Leisure & Sports Industry Sector, one of the firm’s fastest-growing practice areas.
Bob Boland: Litigation & Compliance in Sports
A nationally recognized attorney with more than 25 years of specialized experience, Bob has guided clients through complex, high-stakes matters at the intersection of collegiate and professional athletics, compliance, and institutional integrity.
Recognized by Lawdragon for Litigation & Compliance in Sports, Bob also leads the firm’s robust representation of college athletic directors and other sports leaders nationwide. His recent litigation successes include leading Shumaker teams in securing temporary relief against the National Collegiate Athletic Association (NCAA) in four of five eligibility cases on behalf of collegiate basketball and football players.
Bob previously served in a first-of-its-kind role as Athletics Integrity Officer at Penn State, overseeing a $220 million athletic department with direct accountability to the university’s president and board. In that capacity, he led efforts to restore trust and ensure compliance with federal and state law, as well as policies of the NCAA and the Big Ten Conference, during one of the most challenging periods in collegiate sports history.
Beyond his practice, Bob has made transformative contributions as an educator in sports law and ethics. He currently serves as a full-time faculty member at Seton Hall University School of Law, anchoring its Gaming, Hospitality, Entertainment & Sports Law concentration. He has previously led and developed top-ranked sports management and sports law programs at Ohio University and New York University.
His professional credentials include a Title IX Coordinator Certificate from the National Association of College and University Attorneys and past service as an Ethics Committee Member for USA Weightlifting. A player agent for more than a decade, Bob has negotiated more than 100 playing, coaching, and endorsement agreements across multiple sports. He is frequently sought by national media for his insights on Name, Image, and Likeness (NIL), sports wagering, and Title IX.
Bennett Speyer: Disputes & Investigations in Sports
Bennett is an influential figure and trusted advisor in the sports industry, counseling clients across both the collegiate and professional landscapes. He plays a central role in developing client strategies and expanding the firm’s national footprint in the sports industry. Bennett’s clients include college and professional athletes and coaches, athletic directors, conference commissioners, and other industry executives, as well as university athletic departments, leading complex negotiations and navigating sensitive and high-visibility matters.
Recognized by Lawdragon for Disputes & Investigations in Sports, Bennett is known for his strategic judgment and steady, solutions-oriented approach to sensitive issues and disputes. His work spans high-stakes coaching transitions, multimillion-dollar employment agreements, and separations.
He is also frequently called upon to solve complex tax issues germane to stakeholders in the sports industry, such as the treatment of contract buyouts. Further, working collaboratively with agents, financial advisors, and accountants, Bennett has developed a reputation for creatively structuring employment agreements, utilizing deferred compensation and insurance-based strategies to help clients secure their financial future in an industry replete with longevity risk.
“Bob and Bennett embody the excellence, judgment, and leadership that define Shumaker’s nationally recognized sports law practice,” said Jennie Compton, Shumaker’s Managing Partner and Chair of the Management Committee. “Their recognition by Lawdragon reflects the strategic counsel, steady guidance, and results-driven advocacy they deliver to our clients every day—helping athletic leaders and institutions navigate complex challenges with clarity, confidence, and long-term vision.”
Shumaker’s national Sports Law practice represents a diverse group of coaches and athletic directors at NCAA member institutions, as well as institutional clients in collegiate and Olympic sports, professional franchises, professional coaches, and other sports figures and entertainers. Lawyers in the group collaborate with clients and their agents, accountants, and financial and other key advisors to create comprehensive career and financial plans and work collaboratively protect the contractual and intellectual property rights of clients.
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