Colorado resident, Brian O’Leary, passed away on December 15, 2023, in Fort Collins, Colorado surrounded by his wife, close family and friends.

Born to John and Josephine (Urbanc) O’Leary on May 31, 1952 in Cheyenne, WY, he moved to Peoria, Illinois when he was seven, graduating from Peoria High School in1970. Brian quickly enlisted in the Air National Guard after graduating. He served in Illinois from June 8, 1970 until August 28, 1974. Desiring to go back to his cowboy roots, he transferred to the Wyoming Air National Guard, starting August 29, 1974, serving two more years. He was honorably discharged on August 28, 1976. 

At 21, he decided to follow in his father’s footsteps hauling for Monfort of Colorado as their youngest driver, and found his passion for being on the road behind the wheel of his father’s truck. Brian would go on to receive many awards, he was named the Company Equipment Driver of the Year by the Truckload Carriers Association and Trucker News, had multiple awards from the Colorado Motor Carrier Association, and was honored by the Nebraska State Patrol receiving a Public Service award for his life saving measures. Trucking was truly in his blood, and just as his passion for his family history, it only made sense to follow what he was destined to do, but blaze his own path in doing so.

In 1976, he had moved on to work for Henry Hersh Trucking, under Hank Sr., where he was brought under Hank’s wing, fueling even more passion for the industry. It was here he learned about the word “Clean” when it came to trucking, and if you knew him, he prided himself in always having a clean truck, being a clean driver and was clean in his speech. 

By 1983, Brian met the love of his life, Claudia, in Laramie, WY and they were married on October 30th. Claudia would be instrumental in helping him blaze more trails, which he was always sure to credit her for – creating a bond unlike anyone else’s. A penguin he once bought for her when she was sick, becoming an emblem for their relationship, starting a collection that boasts on their Christmas tree and within their home. This began another fun characteristic of Brian’s, donning a road companion on all his travels – an oversized Gorilla, “Gramps” with his arm out the passenger window that became an icon.  

After working for Henry Hersh Trucking, he moved on to Western Distributing Company, hauling beer, then produce, meat, and what would become his favorite – exotic, high-value cars. Here, he hauled for high-profile clientele, with many of them becoming friends and clients along the way.

A dream of his, O’Leary Transportation was born in 2006, after his gained experience, where he provided the ultimate enclosed transport service. Building his 1999 Peterbilt, and 53ft trailer, he was entrusted to haul for many big names like Chip Foose, Shelby-American Factory and Foundation, Garth Brooks’ Teammates for Kids Foundation, the Wilson Collection, and so many more. One of his favorite and most memorable hauls was to transport the Chris LeDoux statue – “The Good Ride” to the Cheyenne Frontier Days Fairgrounds, where it’s proudly located and visible from I-25. 

Brian has seen more miles than one will see in their lifetime, always ready to tell incredible stories, being a devoted CFD season ticket holder, listening to the best music along the way, and living the Cowboy way in everything he did. “Life is a Highway” was not just the quote on his truck, but a true testament to Brian’s life. Here’s to the Highway to Heaven – this one might just be the best ride of his life. 

Brian is preceded in death by his parents: father, John O’Leary; mother, Josephine Urbanc; and son, Cal Ray Candeleria.  

He is survived by his wife, Claudia O’Leary; sister, Kathy Rooney of Cheyenne, WY; brother, Tim (Dora) O’Leary of Cheyenne, WY; sister, Noreen (Frank) Hixson of Cheyenne, WY; Children; daughter, Jennifer (Geoff) Bradley; son, Bart Candelaria; daughter, Nicole (Shane Swett) Candelaria; Nieces and Nephews; Mike Rooney, Patty (Kevin) Wells, Shane Rooney, Shelly (Shawn) Nelson, Jason (Carla) O’Leary, Kelli Jo (Bill) VanHouten, Andrea Ahlf, Ryan (Nikki) Hixon, Nicole Meek, and a truckload of grandchildren and great-grandchildren. 

A viewing will be on Wednesday, December 27, 2023, from 4:00pm – 6:00pm at Bohlender Funeral Chapel in Fort Collins, CO. Services will be held on Thursday, December 28, 2023, at 11:00am at St. Joseph Catholic Church in Fort Collins, CO. A reception will be held immediately following at the American Legion (2124 Co Rd 54G, Fort Collins, CO 80524). Interment will be on Friday, December 29, 2023 at Greenhill Cemetery in Laramie, Wyoming. 

In lieu of flowers, the family and Brian request that you donate to the Chris LeDoux Memorial Foundation, PO Box 266, Kaycee, Wyoming 82639 or to a charity of your choosing.