James R Bennett

The world lost a rare and wonderful man, James Robert Bennett, on Thursday, May 28, 2026.

Jim was born on September 6, 1969, in Butte, America to Teresa (Dolan) Bottrell and James Bennett. Not long after, he moved to Billings, Montana with his mom and his sister, Marnie Bennett. Jim spent a lifetime deeply rooted in the Billings community. He graduated from West High School in 1987 before he moved to Bozeman for college. Jim graduated from Montana State University in 1992 with a degree in finance, which made him a forever Bobcat. At MSU, he was a founding member of Club 126 and a brother in the Sigma Chi fraternity. Friends made in childhood and young adulthood remained close with Jim throughout his life, a testament to the incredible man he always was.

In 1993, Jim entered into the adult workforce under his beloved stepfather, Don Bottrell. Jim began his hardworking career at Northern Line Layers, moving to Vice President and eventually CEO and President of Diamond B Companies. Jim’s business ventures were seemingly endless, though notably include Bottrell Family Investments, real estate, oil and gas, Red Angus cattle, the Boothill Inn & Suites, and The Windmill restaurant and Bar 51. He led himself and countless others through nearly impossible feats. Though he was very proud of his work, Jim remained humble in the face of a lifetime of achievements.

Beyond his work, Jim had extensive community involvement: He was a coach and served as President of Big Sky Little League Baseball, was a Billings Clinic Hospital board member, and was deeply involved with Billings Family Services, just to name a few. The sheer number of lives Jim touched could fill a phone book. No matter the problem, everyone knew who to call—and Jim always picked up, ready to help with a smiling face and a joke to tell.

Jim married the love of his life, Jennifer Bennett, in 1996. They had two children together: Sidney, born in 1998, and Zackery, born in 2002. Jim was a family man through and through. He was an amazing and deeply loving father and husband. Jim did everything for his family, and they are forever grateful for the superhuman he was. Jim’s family role extended to his nieces and nephews as well; somehow, Jim always had more love to give. His heart overflowed, and his family felt that love every day.

Jim had many passions and hobbies: the Bobcats, Yankees, and Cowboys sports teams, golfing, fishing, baseball, all the music in the world (with all song lyrics miraculously memorized), laughter at every opportunity, and spending time with his friends. Jim kept friendships like a collector, like prized possessions he never lost; all those he knew, he loved, and all those who knew him loved him in return.

Jim is survived by his wife, Jennifer Bennett, and his children, Sidney and Zack Bennett; his mother Teresa Bottrell and father Jim (Karen) Bennett; his sister Marnie Bennett and half-brother

JD (Christina) Bennett; his nieces Kelsea Edwards, Jennee (Jordan) Evans, Perrin Chavez, Rayeen, Brooke, Sabrina, and Chloe Bennett; his nephews Riley Edwards, Colton Chavez, and James Patrick Bennett; his sister-in-law Dr. Keri Hill (Frank Chavez); his great-niece Jiana Evans and great-nephew Jayden Evans; as well as numerous aunts, uncles, cousins, extended family, and friends considered family.

Jim is preceded in death by his stepfather, Don Bottrell; his mother-in-law Michelle Reed; his father-in-law Don Reed; and other loved family members.

Funeral services will be held at First Presbyterian Church at 2 p.m. on Saturday, June 6. The Celebration of Life will be held at Billings Hotel And Convention Center following the service. In Jim’s memory, donations can be made to Family Services (https://billingsfamilyservice.org) and Billings High School Baseball (donate through the Education Foundation at https://efbps.org/).

Jimmy, Big Head, Jimmy B, UJ, or I R: No matter how you knew him or what you called him, Jim will be profoundly missed. Please reach out to family, friends, or the Crisis Lifeline (dial 988) in times of darkness.