CLIFF STEIN is a sports law attorney with 30 years of experience in the professional sports industry. He has a unique background and perspective of the industry having worked 8 years as an NFL agent representing NFL players, and 22 years working in the front office for the Chicago Bears. During his tenure with the Chicago Bears, Cliff worked with 4 General Managers, 6 Head Coaches, 2 Presidents, and 2 Board Chairs. He played a pivotal role in managing the team’s salary cap and negotiated over $3 Billion in player contracts during his tenure with the Bears. In his role as SVP & General Counsel for the Chicago Bears, he oversaw all legal and government affairs. His leadership extended to high-level business decisions, including reviewing, negotiating, and executing thousands of agreements, including sponsorship, partnership, media rights, licensing, and business development agreements.
Trusted advisor to businesses, coaches, athletes, agents & collegiate institutions in the following conferences:
As lead contract negotiator for the Chicago Bears, Cliff negotiated contracts for Hall of Fame players like Brian Urlacher, Devin Hester, Julius Peppers and Jared Allen. Beyond negotiations, he consistently worked in the background to provide strategic advice, counsel, planning, and mentorship to General Managers, Head Coaches, Owners, and Senior Leadership on building internal consensus and reaching successful outcomes in all negotiations. Recognized as a leading expert in contract negotiations and salary cap management, Cliff now shares his wealth of knowledge as an adjunct professor of law at Northwestern Pritzker School of Law and University of Miami Law School.
