The Warden Is In

AFTER A SUCCESSFUL CAREER IN PRISONS, ESTELA DERR ‘88 IS INTENT ON GIVING BACK

Estela Derr ‘88 says she’s come full circle, returning to the campus where she thrived as an undergraduate in criminal justice—but this time, mentoring students to follow in her footsteps.

The former Federal Bureau of Prisons warden, who retired from the agency after a 29-year career, says it’s her honor to give back to the University community that gave her so much. “If I had to give advice to my younger self, I would tell her to give what you can,” Derr says.

“Give back to the support system that helped you grow, learn and become who you are.”

A Kaua‘i native, Derr says she hit her stride at Chaminade almost immediately. She made friends quickly, appreciated the one-onone connections she made with professors, and spent too many afternoons to count playing flag football and intramural volleyball.

While Derr spent much of her career on the continent, she says she has tried to maintain a connection to Chaminade, including by serving as a member of the University’s Criminal Justice Program Advisory Board. Now retired, she has more time to give back and so was delighted to be asked to serve as a guest lecturer in several Criminology and Criminal Justice classes.

Derr is proud of her many honors over a four-decade career with prisons, but she says her biggest accomplishment has been reintegrating countless former inmates into communities.

Derr adds she wasn’t always destined for a life in prisons. She majored in Business Administration at Chaminade, but decided to take a Criminal Justice course in her junior year. She recalls her professor inspiring her to think more about law and society.

Derr was hooked and secured a prisons case management position, developing educational, work and life skills programs— all aimed at helping inmates reintegrate into the community.

She says while federal prisons aren’t for the faint of heart, she’s never been deterred from successfully completing her job. “I believe in faith over fear,” said Derr, adding that her time at Chaminade also taught her the importance of self-confidence and finding strength within.

The Federal Bureau of Prisons operates 122 facilities, which house nearly 160,000 federal prisoners across the country. Threeyear assignments are commonplace for top employees with the agency, which is what Derr signed on for when she started with the bureau.

In her application, she said she was willing to move anywhere.

“In 2013, I was promoted as executive assistant and handpicked by Warden Richard Ives in Lompoc, California,” Derr said. “This was my dream job, and it exceeded all my expectations. I didn’t ever want to become a warden until a friend asked me, ‘Are you going to be happy?’”

For two years in California, Derr learned all about what it meant to manage a federal prison.

She said she tackled a long list of issues—from affirmative action and labor union laws to implementation of the Prison Rape Elimination Act, all while helping to shepherd a successful reaccreditation process for the Federal Correctional Institute in Lompoc.

“We were decompressing from the reaccreditation process when my boss received a call,” Derr said. “All I heard was, ‘Yes, she’s ready. She’s going.’ When he got off the phone, I asked him where I was going.” The answer: SeaTac Federal Detention Center in Washington.

She was to be named the new associate warden.

Derr wasn’t sold on the position at first because she was happy where she was. But Seattle wasn’t just a promotion. It was closer to family, including her mother. And she would be grateful for that proximity in 2017, when her younger brother suffered a debilitating stroke.

She went on to serve as the only female associate warden at the sprawling federal prison in Victorville, Calif., working under Warden Cynthia Swain. “It was an amazing learning experience that taught me about inmate management and running an institution of this size,” said Derr.

The facility can house 3,000 inmates and has more than 900 staff members.

Derr says over her nearly three-decade-long career with the Federal Bureau of Prisons, she was exposed to just about everything you can imagine, from riots and staff assaults to suicides and murders to hunger strikes and baby deliveries. All these incidents, though, were highly concentrated at Victorville. What intimidated her the most was the sound of the alarms.

“If you hear those alarms, you don’t know what to expect,” Derr said.

By 2020, Derr was ready to return home to Hawai‘i, in part because her brother had moved back to Hilo with his family. The problem was that there was already a warden in place at the Honolulu facility. She called a friend at the Honolulu prison and joked she would put in for the job.

“If I didn’t get it, I would retire from Victorville,” Derr said.

And it paid off—Derr got the job and ended up wrapping up her career at home.

Happily retired, she says speaking to classes of criminal justice students at Chaminade is among her greatest joys. Her advice to them is to take good risks, like she did: “Get involved in classes and activities that are out of the norm and that make you uncomfortable.”

Why? “This,” she said, “will lessen your fears of the unknown.”