Amy Trask on Success, Al Davis and Leaving a Legacy

Gabe Zaldivar

It’s hard to talk to Amy Trask.

OK, let me try to color that differently. It’s a joy to talk to her, but it’s also a little demoralizing. Wait, let me try that again. Talking to her is an inspiration; it truly is.

It’s just that, well, after 40 minutes you are left looking at your accolades and calendar, a measure of where you’ve been and what you will become; and you begin to think, I have to do more with my life.

It’s that Mamba mentality that the truly great have that I would absolutely love to possess.

Every sentence exudes passion, every word is thoughtful and precise. Eloquence flows effortlessly as she holds court and gives you the key to success. But more on that in a minute.

Trask is an NFL analyst for CBS Sports, but was a diehard Raider for 30 years, serving as the organization’s CEO for 16 of them.

She is also the author of the book “You Negotiate Like a Girl” and the chairman of the board of the Big3 professional basketball league.

It’s that old adage, it's never works if you love to do it. And Trask absolutely loves sports, more specifically that hard-nosed game of strategy the country savors on Sundays.

Finding Football

Junior high is a formative couple of years. Many of us find our love in life, only to suffer unbelievable heartbreak when we discover life doesn’t always work out. Trask found her soulmate as it were, football.

“It's a very cerebral and of course, the game itself. It's fast. It's strong, it's powerful. I fell in love with the game when I was a kid,” Trask said.

And you never quite have a say in what you fall in love with. Trask was all in on this hard-hitting, powerful game of chess played on a perfectly designed gridiron. All despite the fact that her family wasn’t all that into the game.

“I did not grow up in a family of avid football fans,” she explained. That didn’t stop her parents from flying up from Southern California to the Bay Area for every home game when their daughter was the CEO of the Oakland Raiders.

It’s a position she held from 1997 to 2013, and it’s an organization with which she was employed for three decades.

The franchise remains one of the most polarizing in sport. You either love them or hate them; their beloved owner Al Davis was just as divisive among fans. But it’s clear that Trask was smitten from the start.

“It didn't matter to Al (Davis). If someone was labeled a behavior problem. And having been labeled a behavior problem when I was in kindergarten, that resonated with me,” Trask said.

While a student at U.C. Berkeley, Trask reached out to the team, inquiring about an internship. And it’s from that entry position that Trask worked her way up, doing just about every job imaginable as she continued her schooling and working her way through law school.

And much like serendipitous parties joined by fate, the two followed one another. The Raiders to Los Angeles just as Trask was attending USC for graduate school and again back to the Bay Area when the Raiders packed up shop and headed back to Oakland.

Two years after that move the team would name Trask its CEO, which is par for the course for an owner indelibly linked to forward-thinking.

The Legacy of Al Davis

Trask wrote about Davis in a 2016 column for Sports Illustrated, explaining that while the former Pittsburgh Steelers executive Dan Rooney has a rule named after him dedicated to diversity, it was Davis that exemplified a color and gender-blind brand of leadership.

“On one occasion, when explaining to a few people that he didn’t swear at women, he noted that he did swear at me and explained that he didn’t think of me as a woman. Case closed,” Trask wrote at the time.

In speaking with me, the CBS Sports NFL analyst regaled Davis with glowing praise for the opportunities he nurtured long before others in the industry, cultivating a meritocracy based on who the best person was for the job at hand.

“I believe we'll all agree that this is someone who decades before these were even topics of discussion, hired without regard to race, gender, ethnicity or any other individuality, which has no bearing whatsoever on whether one can do a job,” Trask said.

“He hired Tom Flores. He hired me. Then he hired Art Shell. And my point in noting it chronologically is this wasn't a one time (thing). So, while the conversation or the topic of women in sports is broadly and widely discussed now, it wasn't even a topic back then.”

The Raiders care about one thing and one thing only, if you were one of them.

She tells a wonderful story about Raiders legend Gene Upshaw, present when someone from the media apparently shouted a jab into the ether, asking what he thought about having a girl work for the team.

“She's not a girl; she's a raider,” Upshaw shot back.

The Secret to Success 

“You know, in my early years, I would go in on Saturdays and I would—I did this as a young employee—I just I went into the ticket office every Saturday and I alphabetize the will call envelopes because I saw that they were sitting on the ticket office employee desks,” Trask recalled.

I love talking to people like Trask. You get to pick the mind of someone who not only made it to the show, but ran the show, helped shape what the show looked like.

Maybe, just maybe, you get to glean the secret sauce to success. Thankfully, the secret is easy. Unfortunately, it’s also remarkably hard to follow it correctly.

Amy Trask is a worker. It’s what she does. She gives her all to any task to which she endeavors, and she is constantly saying yes, even when the possibility terrifies her.

Photo Credit: Amy Trask

Shortly after she left the Raiders, Trask was offered an amazing opportunity to be an analyst for CBS Sports. It’s at this network that she had to do something she never thought she was capable of doing.

“Joining CBS Sports, I faced my biggest fear,” Trask said. “My biggest fear, and this goes back my entire life to the time I was a little kid, is a fear of being on camera.”

The fear goes back decades. Family pictures and videos remain devoid of her presence precisely because of the trepidation.

It would make sense, then, to turn CBS sports down. However, she thankfully got some sage advice from an unlikely source. She had been regaling friends with her offer and the personal hurdle she had to overcome to take it.

“A woman in this group, not someone with whom I was particularly close, someone that was part of the larger group, said in a very, very, very quiet voice, ‘Let it go.’”

We so often shy away from things our gut tells us to pursue. Never embracing the moment fully, which is a shame. Because the rewards are evident.

“And I did let it go,” Trask said. “And I joined CBS Sports and I was so scared, so scared of being on camera. I was in tears at times. But I've learned to do it, and now I'm having so much fun that if there are young girls or boys reading this or men or women reading this who are stopping themselves from trying something because they're too scared, I can only share with them that I can't imagine being any more frightened of being on camera than I was. And now I'm having a great time.”

If you find yourself hesitating in a similar fashion, Trask has an additional salvo of advice, “Look in that damn mirror and tell yourself you can do this.”

Forging Ahead

Trask is a pioneer, there’s no getting around that fact. And the thing with pioneers is they don’t set out to become pioneers, they merely follow their passion and succeed despite an unrelenting and opposing force.

But the reason they are pioneers is they don’t recognize that force. “It really doesn't. And I mean that sincerely,” Trask said to my question on whether her status as the first female NFL executive ever hits her.

That’s the thing about innovators, they are too busy forging ahead to worry about anything else.

Trask tells me about her mother, an educator with graduate degrees in chemistry and education. Someone who never considered not succeeding despite remarkable opposition.

“She was a chemistry major at a time when women just really didn't do that,” Trask said of her mother.

After college, her mom went to get a job, armed with a sterling collegiate record. But she noticed that despite her accolades nobody hired her, so she finally confronted one of the companies interviewing her.

“And they looked at her and they said, you're a stunning woman with a very large diamond on your left hand. Nobody's gonna hire you.”

Pioneers forge ahead.

“She never for a moment considered herself a pioneer,” Trask said. “She never for a moment considered that she did anything out of the ordinary or extraordinary.”

For this NFL analyst and former NFL front-office executive, it’s really quite simple. In life, success comes when you accomplish the task at hand. It’s not at all convoluted a process, “we do our jobs.”

The conversation comes back to gender, something this executive turned TV analyst keeps in the background.

“Look, obviously, I had the tremendous, tremendous, tremendous fortune of working for an organization owned and led by a man who was absolutely unconcerned with my gender. And that sent a very strong, powerful message,” Trask said.

“I didn't spend one minute thinking about my gender. It always struck me as counterintuitive and it still does. It also struck me that it was a waste of my time. If other people wanted to waste their time worrying themselves to pieces about my gender. Go ahead, waste your time. I'm not going to waste my time thinking about it.”

In the Raiders organization, hard work mattered. It was the only thing that mattered.

While you won’t get her to call herself a pioneer or even consider the notion, Trask is adamant that she wants to be a beacon for the younger generation. And she calls on all of us to do the same. It takes a team, after all.

“They can do anything. And let's help them dream,” she said.

“Let's encourage them to pursue their dreams. And let's help them pursue those dreams. Let's be for them. What Gene (Upshaw) was for me in that moment.”

It’s time for the NFL to put Amy Trask into the Hall of Fame, not as its first woman inductee but as an executive who put team before self, who forged a path for those behind her and showed the most sustainable method for prolonged success.

“Hard work matters. It really, really matters. And I often say to people, work hard, work as hard as you can. And when you don't think you can work any harder, find a way to work harder.”