A childhood dream that refused to dim in adulthood seemed like it might not be realized for Colorado Springs police Sgt. Olav Chaney.

After jumping out of aircraft while serving four years in the Army’s 82nd Airborne Division, it took him multiple tries to pass the battery of assessments required to become a police officer.

“I tested five different times,” Chaney said Thursday in an interview, after Colorado Springs Mayor Yemi Mobolade announced to a crowd of 900 attendees at his annual State of the City address that Chaney soon would retire his badge.

Part of the reason for the difficulty he had in gaining entry into the law enforcement brotherhood, Chaney said, was that when he started the process in 1985, he competed against some 3,000 other applicants for 20 openings.

“It was tough competition. I’d test every year, and they finally said yes,” he said. “I really wanted to do this job — I wanted to protect and help people.”

Watching his favorite TV show while growing up, “The Blue Knight,” taught Chaney “you could be a good cop by learning about people and getting to know them.”

Nearly 35 years later, it’s admittedly going to be challenging for Chaney to give up the work because he said he still enjoys it very much.

“It’s hard for me to leave. I’ll be 65 in November, and it’ll be bittersweet. But it’s probably time for a change.”

During his career, Chaney has had several assignments in the Colorado Springs Police Department, including street patrol officer; a plain-clothes officer for the Investigative and Special Operations Bureau in the Metro Vice, Narcotics and Intelligence Division; a member of a Patrol Impact Team that focused on property crimes; and since 2020, the head of the Homeless Outreach Team.

He joined the Honor Guard in the early 1990s, shortly after becoming a police officer, and rebuilt the cadet Honor Guard, which he continues to oversee. He’s also a cadet adviser for teens and young adults ages 14½ to 21.

He wore his ceremonial Honor Guard uniform on Thursday and helped present the colors at the event.

Joining the Colorado Springs Police Department’s Honor Guard in 1992 and serving as a member ever since is meaningful, Chaney said, because the ceremonial tribute pays respects to fallen officers or retirees and their families.

There’s also some levity mixed in. During Christmas-present drives the young police cadets participate in, Chaney has been known to put on the traditional red-and-white Santa Claus outfit to help deliver presents to needy children.

He’s seen the best of the best of police work and the most difficult of times, including losing one of his two work partners on the vice and narcotics squad. Detective Jared Jensen was fatally shot in 2006, while attempting to arrest a parolee who was wanted for attempted murder.

“We were looking for this guy, and the loss was a really tough time for everyone,” Chaney said.

He also helped solve one of the city’s most grisly murders, the 1997 slaying of a local college student, Jacine Gielinski, which he called a dark time and a case that stuck in his mind as horrific.

No matter the specific duty, Chaney has tried to live by what his dad, a 22-year military veteran, taught him, which was to serve people.

He’s known for his ability to calm people down, including during three days of Black Lives Matter protests in 2020 after the murder of George Floyd in Minneapolis.

Using a bullhorn and anti-violence tactics, Chaney helped disband a throng who demonstrated in front of the city’s central police station downtown and had the potential to escalate to violence.

One protester handed him a flower as a gesture of goodwill.

Chaney said some people he’s come across in his line of work have come up to him years later and thanked him for helping them straighten the crooked course of their lives.

In his current role as the leader of the Homeless Outreach Team, he oversees teams of police officers who walk the streets and enter homeless encampments daily to not only hand out essentials such as water bottles and socks, but also make arrests on outstanding warrants, issue citations for violating camping bans and other illegal behavior, and notify people of upcoming cleanups.

“I think Sgt. Chaney is a strong and compassionate leader of the Homeless Outreach Team,” said Beth Roalstad, executive director of Homeward Pikes Peak. Since 2018, her organization has accompanied police on street outreach to help homeless people sign up for services, including transitional housing.

“While we may have slightly different approaches, he’s always been very respectful and sought out the best solutions for the homeless while carrying out the mission of the police force,” Roalstad said.

These days, police officers who work with the homeless community are half social worker and half law enforcement, Mobolade, the mayor, said he’s learned from Chaney.

“Their mission is more than enforcing the law — it’s about offering hope and health,” Mobolade said.

Skye O’Neill, outreach and health care peer specialist for Serenity Recovery Connection, who has worked with Chaney and his crew, said Chaney keeps an open mind and a genuine, nonjudgmental spirit.

“Sgt. Chaney deeply believes in people’s ability to overcome challenges and guides his team with kindness and strength,” she said.

Chaney is willing to sit and talk with people who are in a vulnerable moment and offer support and resources, O’Neill said.

“To say he will be missed is an understatement — his legacy will live on through his team and throughout this city,” she said.

He’s been inspirational not only to professional associates and community members but also the six children he and his wife, Wendy, have together. His oldest son and daughter and son-in-law work for the El Paso County Sheriff’s Office.

“When my wife and I met, she had two children, I had two children and we had two children, and with three girls and three boys, we called ourselves The Chaney Bunch.” Now, the family includes 27 grandchildren.

Chaney began the journey toward retirement four and a half years ago, with a five-year timeline. He’ll leave his post at the end of that window, on Feb. 20, 2026.

“To me, this job is a calling and not just the job,” he said. “It’s making a difference in people’s lives, and that’s what I’m going to miss the most.”