Cover photo for Robert Winner's Obituary
Robert Winner Profile Photo
1965 Robert 2022

Robert Winner

September 16, 1965 — December 29, 2022

ROBERT FRANCIS WINNER, 57, passed away December 29, 2022 at Ruby Memorial Hospital surrounded by his wife and family following a courageous four-year battle with multiple myeloma. He was the son of Leonard and Shirley (Drees) Winner. He was proceeded in death by his father-in-law, George W. Stevens.

Bobby worked for his father's trucking company, Leonard Winner & Sons Trucking, until 1999. Afterwards, he worked at CSX first on the track crew and later as a machinist. He formed many friendships during his years at CSX and found it extremely difficult when he had to stop working due to his illness. Bobby had a strong work ethic and prided himself on keeping his home, vehicles and yard in impeccable condition. He enjoyed deer hunting, especially when he was able to hunt with his grandsons and father. He enjoyed vacations in the Caribbean and last year took his last beach vacation with his wife, son-in-law and grandsons. In addition to his parents, Bobby is survived by his wife of 36 years, Kim; one daughter, Amanda and husband Jimmy Filer; two grandsons, Noah and Evan Filer, who were the light of his life; one brother, Leonard "Bud" Winner and wife Dena; two sisters, Barbara Filer and husband Woody and Denise Ingrodi and husband Mark; brother-in-law, Wayne Stevens and wife Lennie; and mother-in-law, Vivian Stevens. He is also survived by numerous nieces and nephews, as well as special cousin and friend, Tommy Winner. In addition, he leaves behind his special pup, Gracie, and great-grand pup, Addie.

The family would like to give special thanks to Dr. Kevin Shannon, Kelly Fitzwater, Jamie Beeman and the entire oncology team at Garrett Regional Medical Center for the loving care provided over the past four years. A heartfelt thank you as well to all family members who offered help and support during Bobby's illness.

Friends will be received at Durst Funeral Home in Frostburg on Monday, January 2, 2023 from 10:00 to 12:00. A funeral service will immediately follow with Jim Taylor officiating. Interment will be at the Finzel Cemetery.

Words of comfort may be sent to the family following the obituary at

To order memorial trees or send flowers to the family in memory of Robert Winner, please visit our flower store.

Service Schedule

Past Services

Public Viewing

Monday, January 2, 2023

10:00am - 12:00 pm (Eastern time)

Enter your phone number above to have directions sent via text. Standard text messaging rates apply.

Funeral Service

Monday, January 2, 2023

12:00 - 1:00 pm (Eastern time)

Enter your phone number above to have directions sent via text. Standard text messaging rates apply.


Visits: 4605

This site is protected by reCAPTCHA and the
Google Privacy Policy and Terms of Service apply.

Service map data © OpenStreetMap contributors

Send Flowers

Send Flowers

Plant A Tree

Plant A Tree