Howard R. Bailey, age 85, of Helena

Howard Roger Bailey, age 85, passed away on August 14, 2025 surrounded by his family. Howard was born on April 8, 1940, in Boulder, Montana, and raised in East Helena, before settling in Helena, where he spent most of his life.

Howard entered the Marine Corp in August of 1957 where he proudly served as a Military Policeman.  After his honorable discharge, he returned to Helena where he joined the Helena Police Department, and later briefly became the Chief of Police for the City of East Helena. After his law enforcement service, he enjoyed a successful career in the insurance field.

At any family gathering you could find Howard sitting at a table playing pinochle with anyone who he could rope into a game.  You usually did not have any choice if you wanted to play or not.  Howard enjoyed sports and would travel to any sporting event that his kids were involved in and later on when his grandkids were playing.

Howard loved driving and you never knew where he was taking you.  This led to him driving for rental car companies after his retirement.

Howard often had his own time schedule, which he did not bother to let you know.  This resulted in everyone else being later than him at any meal or function even when you thought you were early.  He also would plan family get togethers where everything was planned and a great time was had by all, such as the snowmobile trips to West Yellowstone and family get togethers in Coeur D’Alene and Seeley Lake.

Howard was preceded in death by his parents, George and Mildred Bailey, his older sister, Rose Marie, and his grandson, Hunter Bailey. He is survived by his wife of 47 years, Susan; six children from his marriage to Lillian (Dolly) Thomas; Tammie (Norm) Espenlaub, Tim Bailey, Jennie (Duke) Younkin, George (Lisa) Bailey, Christine Bailey, and Cory (LaNez) Bailey, followed by two children from his marriage to Susan; Brian Bailey and Andrea Bailey; 20 grandchildren; and 25 great-grandchildren.

He was devoted to his family and wanted to be involved.  He will be greatly missed.

A memorial service will be held on August 21, 2025 at 11:00 a.m. at Anderson, Stevenson, Wilke Funeral Home, 3750 N. Montana Avenue, Helena.

Howard will be in interred at Fort Harrison in a private family ceremony.

Service Schedule

Memorial Service

11:00 am to 12:00 pm

Thursday August 21, 2025

Anderson Stevenson Wilke Funeral Home

3750 N. Montana Ave

Helena, MT 59602

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Reception

12:00 pm to 1:00 pm

Thursday August 21, 2025

Anderson Stevenson Wilke Funeral Home

3750 N. Montana Ave

Helena, MT 59602

View map

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