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'Princess of Darkness' Amy Trask embraces nickname, reflects on Raiders career


Amy Trask embodies perseverance. She was the first female CEO in the NFL, but Trask's gender is merely an anecdote in her success. Rather, Trask is defined by her tenacity and grit over a nearly 30-year tenure with the (now) Las Vegas Raiders. She recently joined Madelyn Burke on "Her Playbook" podcast, offering a glimpse into her early career and industry interactions.

Trask recalled her introduction to the game of football. She detailed how the Friday night lights of her junior high experience forever changed the trajectory of her career. "Yes, it's a game of power and speed, but it's a very cerebral game," she articulated. For Trask, the life-sized game of chess was inescapable. She attended the University of California, Berkley during the time when the Raiders were stationed down the road in Oakland. She leveraged the favorable geography to learn strategy encompassed within the game.

"I was never one to have a plan. I never had a strategy or plan about my career," Trask admitted. She landed an internship with the Oakland Raiders by taking a leap of faith, but she never imagined that a cold call would put her on the path to becoming the club's CEO many years later. 

Trask later understood why she resonated so strongly with the organization: Al Davis, Raiders owner and general manager, took chances on people deemed 'problematic' elsewhere. Trask joked that she was regarded a "behavior problem" from a young age, and the reputation preceded her into her higher education berth. She never shied away from conflict and appreciated that Davis enabled her to be herself from the very beginning – something her mother preached growing up. "To thine own self, be true," she noted as the most impactful advice she'd received.

Trask ascended to CEO by paving her own way in the industry. Her influence radiated league-wide, but she admits she never once regarded her gender as she sat amongst male colleagues: "If I don't want you thinking about my gender, why am I thinking about it?"

Trask acknowledged that many of her male counterparts welcomed her with open arms, including Wellington Mara, the late co-owner of the Giants. "The fact is (many) men went out of their way to lend me their support and to encourage me."

Internally, Trask credited Davis for being ahead of the curve in celebrating diversity and inclusion. His mindset permeated the Raiders organization and cultivated some of her fondest memories.

"I still get goosebumps," she shared, when thinking about how Gene Upshaw – Pro Football Hall of Fame Inductee and former Raiders offensive lineman – rallied around her. "She's not a girl; she's a Raider," Upshaw contested when members of the media visited the facility and took note of Trask's presence out at practice. Davis never sought recognition for his valiant efforts, and Trask complimented his mindset: "Nobody should get credit for doing the right thing."

The legendary "Princess of Darkness" nickname is today synonymous with success, but the title was initially bestowed with malice. "Behind her back, we referred to her as the 'Princess of Darkness,'" Sports Illustrated quoted anonymous colleagues.

In embracing the title, Trask joins Raiders fans in appreciating its acclaimed symbolism.

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