In 1983, 24-year-old Ray Osborne, who was then a police officer with the Easton Police Department, became interested in working for Darien.

“I knew a couple of guys that worked here at the time. They told me it was a good place to work,” he said. “I agreed and stayed for 35 years.”

Osborne, Darien’s 10th chief of police, will retire on Sept. 1. He has been chief since 2017. Capt. Donald Anderson will be taking over as chief.

Career accomplishments

One of the programs Osborne has initiated as chief is the creation of the department’s Juvenile Review Board.

“We take very low-level violators and instead of sending a juvenile to juvenile court, we will divert them to the Juvenile Review Board,” said Osborne, who received his master’s degree in criminal justice at Iona College in New Rochelle, N.Y.

The Juvenile Review Board is comprised of police officers, a school resource officer, school administrators, the youth services director, and other members of the community, according to Osborne. “They hear these cases and the juvenile is tasked with completing some community service projects. They don’t have a juvenile record on file,” he said.

The program has been going on for about 18 months. The juveniles have been convicted of charges such as underage drinking, minor position of alcohol, and a very small amount of marijuana, according to Osborne.

Osborne was also supervisor of the department’s Domestic Violence Liaison Unit. Since he became chief, the program has expanded.

“We now have four officers that are domestic violence liaisons,” he said. “They work with victims of domestic violence and keep them appraised of what’s going on with their court cases, give them advice, and counsel them for information.”

Most rewarding

One of the most rewarding times in Osborne’s career, he said, was when he worked in the detective bureau as a detective and detective bureau supervisor.

“I worked together with guys here and outside the department and other area departments solving cases, giving people closure on cases, giving them piece of mind that a perpetrator was caught — those kinds of things were really rewarding,” he said.

One case involved a DWI arrest he made many years ago as a patrol officer.

“The person came in a number of months later and thanked me and had a letter for me,” Osborne said.

“The man said he was going down a really dark path, getting arrested for DWI, and said I helped open his eyes to get into the programs that he needed, which he said probably saved his life,” Osborne said.

Miss the most

As he reflected on his time in the department, Osborne said he will most miss his colleagues.

“I will most miss working with such a great group of men and women here,” he said. “More than half of my life has been spent in this place, so you really make a lot of lifetime friends.”

Fun fact: Osborne, Capt. Don Anderson, and Lt. George “Chip” Vitone were all hired the same day: Dec. 4, 1983.

Osborne added that he’s looking forward to seeing the “younger folks here get promoted to supervisory positions.”

“It’s really rewarding to see some of the younger officers that I’ve observed over the past few years as they move up in ranks,” he said.

Next chapter

Osborne and his wife Susan have two grandchildren, with whom they plan to spend more time.

Their son Ray Jr., is a naval officer in the military.

“He is away a lot and we hope to help out,” Osborne said. “He is based out of Norfolk, Virginia. My wife and I will have the flexibility to help and travel.”

Osborne also plans to continue teaching at Housatonic Community College in Bridgeport as an adjunct instructor in criminal justice. He has been teaching on a part-time basis since 2000. This fall, he’ll be teaching a police ethics class.

“I get a lot of enjoyment out of it,” he said. “I’ve mostly taught criminal investigation and crime scene processing. I’ve done a little bit of intro to law enforcement and some contemporary issues in criminal justice classes.”

Classic cars

One of Osborne’s favorite hobbies, which he plans on spending more time on in retirement, is refurbishing old cars.

“I’m a classic car guy,” Osborne said. “I own a ’67 blue Mustang that I’m restoring.”

“I still drive it,” Osborne added.

His father was a mechanic and Osborne would often work closely with him when he was young.

“Before I became a police officer, I worked in the auto parts industry and did machine shop work,” Osborne said, adding that he goes to a lot of car shows.


“On behalf of the Town of Darien, I want to thank Chief Osborne for 35 years of dedication to the Darien Police Department,” First Selectman Jayme Stevenson said. “We are fortunate to have professionals like Ray and many others who have chosen to spend nearly their entire law enforcement career in Darien. This speaks volumes about our community and how highly we value our law enforcement and first responder professionals.”

Stevenson continued, “While Ray’s departure is sooner than I anticipated, he’s accomplished much in his two years at the helm including his support for the Juvenile Review Board, which has been a tremendous success in helping our kids stay out of the juvenile court system for first/minor offenses.”

Additionally, “Ray has helped develop a department filled with highly skilled police officers, some of whom will become our new department leadership. Ray has provided exemplary leadership at a time when societal and technological influences make the job very challenging. We wish Ray all the best in his retirement and are deeply grateful for the sacrifices he and his family have made in his 35-year service to the town of Darien.”

‘Very proud’

Osborne said he’s “very proud” that he has served in multiple roles at the police department.

“I’ve served in just about every capacity that this department has to offer. I served as a detective, sergeant, lieutenant, captain, and chief,” Osborne said. “I accomplished everything that I wanted to accomplish and more.”

“I’ve had a good career,” Osborne added. “I’ve always given 100 percent.”