Former NFL Exec Advises Students w/Interest in Sports Law on Tackling Contract Negotiation


Former NFL executive Jeffrey Diamond shared insights from the field of sports law with Miami Law students on October 12. Diamond has become active in speaking to law and MBA students across the United States since his recent retirement from the NFL, and his speeches are aimed at providing aspiring negotiators with the tools to find success in their fields.

Jeffrey Diamond speaking to students at Miami Law.

The talk, part of the LL.M. in Entertainment, Arts, and Sports Law program, focused on negotiation and was for all students interested in the area of sports, business and law.

Success from Living by Motto: Tackle the Problem, Not the Peson

Diamond was named "National Football League (NFL) Executive of the Year" in 1999 while working with the Minnesota Vikings following the team’s record-breaking 15-1 season. He attributes his success as a general manager, negotiator, and team president largely to one of his guiding principles.

“My biggest motto always was to ‘be easy on people, and hard on the problem,’” Diamond said.  “That really served me well, and I think it’s a good thing, as you go forward in the negotiating world, in whatever type of legal work you’re doing ... Be easy on people, be hard on the problem, and I think people will respect you for that.”

The Key to Negotiating Contracts in Sports Law

Diamond has considerable expertise in negotiation stemming from the thousands of deals he’s brokered throughout his career. These have included player contracts, sponsorship agreements, stadium leases, coaches’ contracts, and radio/TV deals, in addition to negotiations at the governmental level he partook in as chairman of the Ingram Group, a consulting and political lobbying firm.

“I think that by nature, when you’re negotiating as a management negotiator or as a player negotiator (as an agent), it’s going to be competitive, but you want to try to make it as collaborative as you can in the process,” he said.

“It’s adversarial generally, but you still have to work with the other side, and understand that. So it’s very basic - I think it’s about treating people with respect.”

Reputation and Confidence Are Everything

He noted the importance of reputation in negotiation, recalling his own aversion to dealing with unscrupulous or media-hungry sports agents.

“The reputation you want is to be professional. Have integrity; and you want to be looked at as tough but fair, and a good person to deal with,” he said, “I always try to be positive, not negative, in negotiations.”

He added that confidence is key to getting what you want out of deals: “Being confident is really important as a negotiator - you don’t want to appear weak or uncertain of your position.”

Connection to University of Miami School of Law

Diamond’s connection to Miami Law stems from alumnus Marc Trestman, J.D. ’82, who serves on the advisory board of the Entertainment, Arts, and Sports Law LL.M. program. Trestman, who grew up two blocks from Jeffrey Diamond in Minneapolis, became the first player Diamond signed in the NFL. Trestman is currently the head coach of the Toronto Argonauts in the Canadian Football League.

In addition to speaking to students, Diamond currently consults in management, strategic planning, and marketing for ZeSa Fitness, a fitness startup which has signed close to a dozen deals to provide fitness equipment to NFL teams.

He concluded his lecture by warning that while his advice may better prepare students to be successful negotiators, there is never complete certainty in sports or business negotiation.

“You just never know what’s going to happen in the world of sports, or really in business, too. It’s just crazy how it can all happen.”

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