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Amy Trask Literally Wrote The Book On Women In The NFL

The former CEO found success with one of America’s most famous sports franchises

Thirty percent of the National Football League’s (NFL) front-office jobs are currently held by women. One of the first to make her mark there was Amy Trask. The Angeleno’s 30-year stint with the Oakland—then Los Angeles—Raiders began with an unpaid internship and progressed to CEO. Indeed, at one point, Trask was the only woman in the room at NFL owners meetings. Trask resigned from the Raiders in 2013.

Recently, the NFL announced its commitment to the inclusion of women beyond the front office. As the organization’s new director of football development, Sam Rapaport is encouraging women to step into positions from scouting to coaching. It’s definitely been a time for firsts, with Sarah Thomas serving as an official; Jen Welter coaching with the Arizona Cardinals; Kathryn Smith coaching with the Buffalo Bills; and Cathy L. Lanier coming on board as the NFL’s head of security.


Trask, whose book You Negotiate Like a Girl: Reflections on a Career in the National Football League was released this month, isn’t surprised by the increase in gender inclusion. Asked about offering advice to women joining the NFL’s ranks, Trask is quick to say they don’t need it. But, “Were I to share any observations with them it would be this: Do your job and don't spend any time thinking about your gender.”

Now a football analyst for CBS Sports, Trask shares with GOOD more wisdom and insights garnered during her years in the sport.

What do you love about the game of football?

Football is a very cerebral game, which I’ve long likened to a game of chess. It’s a game of matchups: How do we match up at the line of scrimmage? Can my left tackle handle his man, or do I need to give him help? How do my corners match up with your receivers? Can they cover them man to man, or do we need safety help? The best coaches position their players and teams to exploit matchups to their advantage and to defend against matchup discrepancies. Yes, football is an exciting game—the speed, the power, the skill—but it’s also a cerebral game.

During law school at the University of Southern California (USC), you cold called the Raiders about a creating an unpaid internship for you. Did you have a career path you were aspiring to in the NFL?

Though I was in law school at the time, I had no intention of ever practicing law. I wanted an opportunity with the Raiders and would have done absolutely anything—worked in any department—for such an opportunity. As an intern, and then later as a full-time employee, I wanted to learn absolutely everything about the organization and volunteered to do anything and everything I could.

There’s suddenly much talk about women and “firsts” within NFL history. Do you remember any of yours?

[quote position="right" is_quote="true"]I’ve never walked into any setting … thinking about my gender. [/quote]

There were many instances throughout my career when I was told I was the first woman to do something. That never mattered to me. It’s always struck me as counterintuitive and antithetical to consider my gender if I don’t want it to be a consideration for others. I’ve never walked into any setting—an NFL owners meeting, a meeting of Raiders ownership, a football meeting—thinking about my gender.

Are there more chairs in the room for women now?

There were many changes over the almost 30 years I was in the league and there’ve been more since I left. Today, Jeanne Bonk is executive vice president and COO of the San Diego Chargers and Hannah Gordon is the general counsel of the San Francisco 49ers. Both of these women do spectacular jobs for their respective organizations.

During your journey with the Raiders, what lessons did you learn along the way?

I learned that it's OK to make mistakes in business. Someone once told me the only business people who don't make mistakes are those who aren’t trying to create and innovate. I also learned it’s of paramount importance for everyone in a business to communicate, cooperate, collaborate, and coordinate. The only mistake for which I have little, if any, tolerance is a failure to do so. When I assumed a leadership role in the NFL, I emphasized to employees that it's absolutely OK to make a mistake.

What contributed to your success?

Hard work and passion. I understood from the moment I began my internship until the day I resigned, that working for the organization was both a privilege and opportunity of a lifetime.

For those who don’t know, how did you get the nickname “Princess of Darkness”?

Mike Silver wrote a piece for Sports Illustrated in the early 2000s in which he quoted a league official as saying that was the moniker often used to describe me. Certainly, it wasn’t intended as a compliment. Yet, Raider Nation embraced it and I embraced it. I love and cherish my nickname.

What made you decide to write You Negotiate Like a Girl: Reflections on a Career in the National Football League?

I love to write. For a period of my childhood, I thought I might be a writer. It struck me as a wonderful adventure to write a book, so I did. There’s nothing deep or profound behind my decision to do so.

From the book, what would people be surprised to learn about your relationship with former Raiders owner Al Davis?

[quote position="right" is_quote="true"]When I assumed a leadership role in the NFL, I emphasized to employees that it's absolutely OK to make a mistake.[/quote]

The biggest misconception about Al was that he didn't tolerate disagreement and wouldn't harbor anyone who disagreed with him. Were that the case, I would’ve been fired two or three weeks after I was hired on a full-time basis. I disagreed with him throughout my career. At times, it struck me that we disagreed more than we agreed.

What are your thoughts on the NFL recently hiring Sam Rapaport to work toward opening the door for more women in roles beyond the front office?

I had the privilege of working for a man [Al Davis] who hired without regard to race, gender, ethnicity, religion, or any other characteristics that have absolutely no bearing on whether one is qualified to do a job. That's the way business should work. That's the way the world should work. In my view, businesses that don't hire in that manner deserve to fail for two reasons: it's wrong and it's dumb.

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