Shining a spotlight on celebrities and athletes who love to travel. Created and developed by Stacy Steponate Greenberg.

In the history of pro football, there have been many unforgettable nicknames: The Galloping Ghost, Crazy Legs, Broadway Joe and Prime Time, to name just a few. But who would have guessed that the all-time coolest nickname in football would belong to a woman? Well, it does. Meet Amy Trask, The Princess of Darkness. Impressive. Inspiring. Insightful. She began as an intern in the legal department for the LA Raiders and remained with the organization almost thirty years, ultimately being named CEO, making her easily the most powerful woman in America’s most powerful sport. Ask Amy about being the first female team executive in league history and you quickly learn that she often didn’t realize she was the only woman in the room; gender was irrelevant, she was a Raider. Loyalty and toughness were her trademark, and soon the world will come to know so much more as Trask is writing a book, “You Negotiate Like a Girl”, about her experience in the NFL. Now working as an analyst for CBS Sports and CBS Network, the Overhead Compartment took to the gridiron with Trask to find out about her love of the game and what life from the inside of an NFL team really looks like.

The Overhead Compartment with Amy Trask begins now…

OC: You spent 16 years as the CEO of the the Oakland Raiders. What are your top three memories?

AT: · January 19, 2003 – the AFC Championship Game – Zack Crockett scored late in the 4th quarter – the play was 12 Blast – it was at that moment I knew we were in the Super Bowl.
· January 2, 2000 – the final game of the 1999 season – we kept the Chiefs from making the playoffs – the game included a spectacular Tyrone Wheatley run, dubbed the Run of the Millennium – did I mention that we kept the Chiefs from making the playoffs?
· Any time we beat the Jets.

OC: You worked for a legendary figure, Al Davis. His persona was larger than life, how was the man different from the image?

AT: He was different in many respects, more than I can briefly recount. Perhaps the biggest misconception about Al is that he would not tolerate disagreement or anyone who disagreed with him. Were that the case, I would have been fired roughly two weeks after I began my job.

OC: Which NFL city did you always most look forward to visiting?

AT: I didn’t look forward to cities, I looked forward to stadiums and to game day. I did have an enormous preference for warm weather locations, as I hate cold weather. Two of the coldest games during my years with the team were Green Bay (in December) and Buffalo (in January). I loved preseason games in Arizona. August in the desert – warm and wonderful. Well, warm by my standards, miserably hot in the judgment of most of our players who shared with me that they were not amused by my expressions of glee about the weather.

OC: What did you do when you had down time in that city?

AT: On one night trips, I had no down time. On two night trips, I explored the city in which we were staying. After the walk through and once the televising network had finished its work, I left the hotel on foot and I walked and walked and walked. I never had a destination in mind, I just explored. No matter how many times we’d played in any particular city, I loved to do this. I frequently got lost, which I think is the best way to see and learn about a city. In fact, it was my hope that I’d get a bit lost (I hoped that someone would help me if I couldn’t find my way back).

OC: You were the first female Chief Executive in the National Football League, what advice would you give to young women working in male-dominated industries?

AT: The same advice I would give a young man: work hard, work really, really hard, work harder than you ever imagined you could, and stop thinking about the fact that you’re a woman. Do your job.

OC: Your book “You Negotiate Like a Girl” is due out this coming September. What is the one thing you hope readers will take away?

AT: To thine own self be true. That is spectacular advice which my mother often shared with me (and that Polonius shared with Laertes, in Hamlet).

OC: The Overhead Compartment discovered that you view ice cream as a daily necessity and sometimes, an actual meal. How did you arrive at that conclusion?

AT: It is either inherited or learned behavior. I have the same ice cream habits as my mother – we both eat ice cream numerous times a day and we both believe that it can, indeed, be a meal. At any given moment we each have at least eight flavors in our respective freezers. I just looked in mine, at this moment it houses twelve flavors.

OC: What is your favorite flavor?

AT: I have no favorite, but I don’t like ice cream that has “nothing in it.” I like chips and chunks and veins and swirls, pieces and bits and bites. Toppings are also a necessity. The sprinkle to ice cream ratio is of critical importance.

OC: Where did you have the best ice cream you ever found?

AT: I am not at all picky about brands. That said, my favorite ice cream spot is Fenton’s (in Oakland). I started visiting Fenton’s while in college (nearby, in Berkeley) and was thrilled that when Al moved the team back to Oakland, I’d again be close to it. Most people visit Fenton’s for special occasions or only on occasion. I was a regular – and by regular, I mean more than once a week.

OC: It’s well known that you are close with Ice Cube. We need one good story.

AT: I tried to convince him that we should do a rap version of It’s a Small World. He tried so hard to be diplomatic and delicate when graciously declining, but the look on his face spoke volumes – it was sensational – he thought I was nuts. I still think it’s a good idea. The message in that song is spectacular: there is just one moon and one golden sun, and a smile means friendship to everyone. Ice Cube – we really need to do this.

OC: What’s the strangest thing that ever happened to you on an airplane?

AT: I had the tremendous privilege and pleasure of flying with the California Air National Guard in an F16. At one point, I said into my headset: hey, we’re upside down. The fighter pilot responded that we had been for a bit of time – he was amused that it took me so long to realize that we were.

OC: What is your favorite place for leisure travel?

AT: Any place with sun, sea, sand and surf – any warm place on the ocean. I’m partial to Mexico and Hawaii because they are close to California and thus easy to get to.

OC: Biggest pet peeve about hotels?

AT: Noisy rooms. I don’t want to be near an elevator lobby, a stairwell door, a noisy hallway or any place with noise. I want a quiet room. Oh – one more thing – I can’t stand when the hotel inserts its judgment for mine and moves the clock ten minutes ahead. This just happened in San Francisco (for the Super Bowl). I realized when I checked in the clock was ten minutes fast, which I don’t like, so I changed it. Every single morning the hotel staff changed it back. It made me crazy. I like “real time,” not “ten minutes ahead” time and I had to fix the clock every day, after the time was changed.

OC: Top three favorite restaurants anywhere in the world.

AT: I don’t like fancy shmancy. My favorite food is Mexican food – if I could only have one genre of food for the rest of my life, it would be Mexican food. And it need not be ‘fancy’ Mexican food – in fact, the grungier the location, the better. Mexican food by the beach is heaven.

OC: You grew up and currently live in LA. As a true local, what is the biggest misconception about the city?

AT: That our traffic is worse than that in any other large metropolitan area in this country. Guess what? Traffic is just as bad in the Bay Area as it is in Los Angeles – actually, in some regards it’s worse, because when one is driving across a bridge, one can’t get off and take a side street. And guess what? Traffic is just as bad in New York, too – often worse – both in Manhattan and when traveling to Manhattan from the airport. News flash: big cities have traffic, Los Angeles is not unique in that regard.

OC: Complete the following sentence: I never leave home without:

AT: Snacks. Really and truly – I never leave the house without snacks.

Amy Trask, please use care upon departure as items may have shifted in The Overhead Compartment during our journey. Thanks for choosing us for your travel tips! Have a wonderful day!