The HILLTOP Award (Heroes Inspiring Leadership, Learning, Teamwork, Opportunity and Pride) was created in 2006 to honor individual and organizational efforts to address poverty in Multnomah County.

Trent Gay is the HILLTOP Award for Agency Staff/Volunteer Achievement winner for 2019.

Trent Gay

Ten years ago, Trent Gay was on top of his game — literally and figuratively.

He was a celebrated, regional sales leader in the food service field credited with bringing in millions of dollars for his company. While away from work he was on the basketball court, coaching at Jefferson High School for two years. He also served as a coach for the Amateur Athletic Union and United Salad Nike travel team. And he didn’t coach just any AAU team but nationally award-winning ones with players that included Klay Thompson, Kevin Love, Isaiah Thomas, Kyle Singler, Avery Bradley and Terrence Ross.

During the summers, he ran a life skills business for underserved youth who he helped provide summer jobs, clothes and travel expenses to play basketball. He was a husband and a father of two with a home in Lake Oswego.

“In 2009, I had addiction issues and I lost my job at United Salad,” Trent said in a recent interview. “I was charged with possession of cocaine which became a misdemeanor. I really struggled during that time and went through a divorce.’’ Then, about five years ago, he became homeless.

Today, Trent is in recovery. He has a home and a job — as a career coach with Central City Concern. And, he’s been chosen for the 2019 HILLTOP Agency Staff Achievement Award as an agency staff member or volunteer who has demonstrated an extraordinary capacity for helping individuals, families and communities resolve issues of poverty.

As a former Central City Concern client himself and then employee who worked his way up as an on-call janitor, Trent has helped nearly 100 people experiencing homelessness access education opportunities, employment, jobs and housing. Through a grant from A Home for Everyone, he works with partner agencies to provide the best services possible, even for those who may have stumbled many times.

He goes above and beyond in advocating for clients, says Central City Concern program manager Vivian Lackey, helping them advance in their work with promotions and move onto higher paying jobs. He works with partners to extend stays at transitional housing or shelters. And he’s helped find day shelter for clients who work the night shift and just need a place, other than a sidewalk, to sleep.

“He is the most compassionate, flexible, caring, motivating staff to the population he serves that I’ve seen,” Lackey said.

Trent stays motivated by the success of his clients and credits his own success to a great employer and — as a licensed minister — to his faith, as well.

“I had to go through humility to get to where I am,” he says. “How I was able to be very self-sufficient, have a family and a nice home, and lose it all and then be able to work my way back into a position — a lot of times people have to see that you’ve been through what you’ve been through to see that there is success.”