During that time he became what city council member Rick Earnshaw said is, "the school's greatest supporter."
In addition to performing his duties as a police officer, Montgomery attended all the high school's athletic competitions, school plays and other extracurricular activities.
When the department considered changing Montgomery's assignment last year, students were up in arms and gathered 250 names on a petition requesting that Montgomery remain the resource officer.
Speaking of that effort, Montgomery said, "The kids at Woods Cross High are the greatest."
Montgomery joined the department in 1969, when there was only one patrol car shared by five officers.
Through his career with Woods Cross, he has worked patrol, been a detective, and even drove a snowplow in the early days.
"I have knocked over my share of mailboxes," he said.
But he admits being the high school's resource officer was the best part of his career. "It's been one of the greatest experiences of my life," he said. "It's been fun to work with the students and to be a part of the activities."
Some of the kids he dealt with as teens now have kids, even grandchildren attending Woods Cross High.
Much has changed over the years in the department.
"It used to be that we spent most of our time helping in the community, and that was not as much police work as we know it today," Montgomery said.
In addition to working in Woods Cross, he lives there as well and appreciates the community.
He recalls in 1971 when a massive windstorm blew out the windows of his home.
He went on duty that day, taking care of the emergencies the windstorm brought and when he finally got home, the neighbors had boarded up his windows.
"That's the kind of community Woods Cross has always been -- neighbors looking out for each other."
He and his wife Sandy raised two sons in the city, where they have lived for 30 years. They now have four grandchildren.