Chief Magistrate Judge Arthur Boylan certainly knows a thing or two about performing the impossible.

After all, this is the man who successfully mediated some of the seemingly most intractable disputes in business history, most notably the 2011 labor dispute between the National Football League and its players.

But Boylan’s most impressive feat in that case might have occurred during the first day of mediation: He successfully took NFL Commissioner Roger Goodell and players union Executive Director DeMaurice Smith to lunch without anyone noticing.

With hordes of national media parked outside U.S. District Court in Minneapolis, the high-powered trio left through a side door and walked a few blocks down 3rd Avenue S. to the Depot hotel for a bite to eat.

“I don’t know why the reporters didn’t see us,” Boylan said.

Over the next hour and half, the group discussed not the labor dispute but their families and backgrounds. Goodell and Smith went on to regularly break bread with the judge, a practice that built trust and eventually led to an agreement, Boylan said.

“Despite the fact they had so many things they disagreed about, I thought the lunch was a wonderful way to kick off the mediation,” he said. “It turned out [the regular meals were] a successful way to settle the case.”

After 17 years as a federal judge, Boylan is stepping down next year to start his own mediation practice. Throughout his career, he has helped craft resolutions to everything from shareholder complaints and faulty medical devices to police misconduct and trademark disputes. But Boylan doesn’t dare try to resolve disputes among his three children.

He also loves the Chicago Bears and curling.

Go figure.


What’s more valuable to a mediator? Temperament or skill?

Temperament. There is a skill set. One of those skill sets is learning how to be patient. A lot of the value you bring to people is your reputation for your fairness. I’m an effective meditator because I like people. I like to hear people’s stories about who they are. That goes a long way to resolving the cases when I have the people in front of me.


Despite your long and distinguished career, people might only remember you as the man who saved football. Are you OK with that?

I am. It was the most challenging case of my life. It had a lot of parties. It had a lot of money. The economic impact of the NFL on American gross national product is tremendous. I told both sides they had the future of the game in their hands and to their credit, one of the reasons why the case got settled as quickly as it did, was that they both realized they were stewards of a wonderful tradition and a wonderful game and they didn’t want to blow it. In the end, they got it done.


Did both sides really like the final agreement? Or was it better than nothing?

I think both sides felt it was a great agreement. DeMaurice Smith, he was just the sharpest tack. He did a real great job for the players. It was a really tough job because you got how many teams, how many players, how many retirees. It really rolls into the thousands that he was representing. His job was in many respects harder than Roger Goodell’s because he had so many constituents he had to keep happy.

These were tough issues to get over. The one benefit about mediation is that you are not forcing an agreement down their throats, and that builds momentum. When you start with the small agreements, agreeing on one point often leads to another agreement and then the difficult and larger agreements later on.


Did you ever think the whole thing was going to collapse into failure?

Many, many times. That’s when it’s really important for a mediator to not despair. If I don’t settle something, I just don’t truck it up to “Well, we tried our best” and go onto the next case. I really have sleepless nights thinking about how come we didn’t settle. What else I could have done. You have to be patient and resilient and keep on going back to the table.


How did the two sides react when you brought up curling?

They both looked at me like I was crazy.