Remembering Kyle Callaway 

“All of his friends considered him their best friend.” 

“He never knew a stranger.” 

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“He was tougher than anyone.” 

“100 percent cowboy.” 

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“Always super positive, never about losing and always about winning.” 

“He inspired people.” 

“He left us way too soon.” 

Kyle Callaway, a noted PRCA steer wrestler, feedlot owner, and more than anything – son, brother, husband and dad, died February 24, 2025, of brain cancer at age 41. He left behind his wife, Anna, daughters Elsie and Cleah and son, Huckleberry, as well as his parents, Gregg and Debbie Callaway, and brother Cody and sister-in-law Tiffany Callaway and their daughters Mesa and Hazley. His in-laws include Norm Haaland and Norma Haaland and sisters-in-law Jackie Haaland and Bernie Swanson, her husband, Vince, and their girls, Maddie and Grace. 

In addition to family, a network of friends stretching from Canada to Mexico are mourning the loss of a cowboy known for his talent, magnetism, and positivity that remained until his death.  

Kyle grew up in Sterling City, in West Texas, where life was wide open for a young boy. He told stories of how the second school got out he was gone, rabbit hunting. The rabbit bounty was $1 a head, and Kyle and his buddy Slade and would hunt all weekend – his parents wouldn’t see them until it was time to go back to school Monday morning. Hunting, fishing, swimming in the river – it was a boyhood filled with dirt and adventure and Kyle lived it to the fullest. “I’d get a lot of calls about what my boys were doing, but they were mostly just havin’ fun,” said his dad, Gregg Callaway. “Everyone for sure knew those two.”  

Kyle grew up around horses and cattle, but his rodeo interest really came later in life, said his brother, Cody Callaway. As a child he was a “sports guy” with deep talent, even as a small statured, “scrappy little kid.” 

Football is a really, really big deal in West Texas. “When Kyle was in junior high the high school coaches started having him practice with their team, prepping him to be the next quarterback,” said Cody. The Callaways moved to Gillette, where Kyle graduated from high school. That’s when the rodeo bug bit him and he started riding bulls, bulldogging and roping. An injury sidelined him from pursuing broncs and bulls, and he got serious about dogging.  

In 2008, in a bar in Gillette, Kyle met a girl: Anna Haaland, a cowgirl from Billings who was on a college rodeo scholarship. 

“Kyle was such a big personality – always the life of the party, everyone was drawn to him,” said his wife. “I am not. We are such different personalities. I’m an introvert, he’s an extrovert.” 

Kyle called after their first meeting to ask if she would come work chutes with him. “My friend Jacey and I went and worked, then went and ate dinner with him. Kyle and I started dating and never looked back. We always had so much fun together.” 

When Anna finished college they were still dating, and she moved back home to Billings to live and work at her dad, Norm Haaland’s, feedlot, Blue Creek Feedyard, south of Billings. “I asked Dad if he had any work for Kyle too, and he said, ‘Oh sure – he can go haul manure at [the other location],'” Anna said with a laugh. “But he knew exactly what I meant.” 

The two started their lives together – feedlot work, nursing school, rodeo, babies and marriage all intertwined. Anna worked as a nurse full time when their daughter Elsie was a baby, but on the days she would take her to daycare, “Kyle would go ride pens, then go pick her up from the babysitter just as soon as he possibly could.” His family was his life. When their daughter Cleah was born Anna returned to the feedlot full time with Kyle.  

“Even though our personalities were different, we were a good team. He was the one in front talking to people, and I was behind the scenes, trying to make all of his dreams and ideas happen.” 

When the longtime feedlot manager retired Kyle stepped into the role. “He could be good at anything. He grew up around cattle, was always a leader and could step into any role and communicate with anyone so well,” said Anna. “He was easy to talk to, everyone liked him.” In 2020 they purchased the feedyard from her father.  

During his years as a Gold-card member of the Professional Rodeo Cowboy Association as a steer wrestler and team roping header, Kyle qualified for the Mountain State Circuit Finals Rodeo, Montana Circuit Finals Rodeo and Turquoise Circuit Finals Rodeo, and competed in the Dodge National Circuit Finals Rodeo in 2008. Anna, who is a breakaway roper, would often haze for him, and he would push calves for her. 

Not only was Kyle handy in the arena, but he was also a true horseman. “He started a lot of his own horses, and he could make a bad bulldogging horse good in the box. He was just good with them on every level,” said Anna. “Even my good breakaway horse, we raised her and he did all the foundation on her and started her in the breakaway.” 

He loved to rodeo, but more than just competing, he loved the people he rodeoed with.  

“Kyle had so many friends, and all of his friends thought of him as their best friend,” said Anna. “Everyone thinks very highly of him – in the rodeo world, cattle world, kid world – everyone who knew him had a meaningful connection with him.” 

He was highly competitive, yet Kyle was never afraid to pass along his success to others. He was a great teacher, and spent time with many younger kids, teaching them to bulldog and sending them with horses to help them start their rodeo career.  

“There were a lot of young kids that Kyle helped get a rodeo career started, and they all remember it – they know it’s on their shoulders now to pass on that legacy,” said Cody.  

In early 2022 a seizure changed the Callaways’ lives. A diagnosis of a malignant Glioblastoma Astrocytoma brain tumor rocked their world, and led them to Arizona, and later Tijuana, Mexico, for tumor removal and treatment. It was a tough blow, but with Anna on board to administer chemotherapy treatments, two days post-surgery Kyle was back home and at a junior rodeo. “We never even slowed down, and we thought ‘That’s that – we just beat brain cancer,'” said Anna. Kyle worked hard to get back to competition, and in the summer of 2022 started entering again. His life was changed, but they were entirely optimistic the worst was behind them.  

When the cancer came back in the fall of 2024, “We just thought we’d do what we did before and get through it,” said Anna. But this time it was different. They bought a place in Arizona and the lived part time in Billings, part time down south for treatment. Friends and family rallied to keep the feedlot going. They returned to Tijuana for treatments, and Kyle never stopped living large. Cody said, “We’d go fight cancer in the morning, and then in the afternoon we’d go down to the dock and hire a boat captain to take us deep sea fishing. Kyle always told us, ‘I’m glad it’s me that got this, because none of the rest of you are tough enough to handle it.'” And that’s what he did – handled it and kept on. Doctors would ask for him to visit their other patients because his optimism was contagious.  

“His attitude was ‘Yeah, we’re fighting, but you can’t stop living,'” said Cody. “And it became a really big deal for a lot of those other patients there to see that positive attitude.” 

He stayed that way until the very end of his life.  

“It kind of snuck up on all of us around him when he passed because he didn’t let us ever believe that he couldn’t beat it,” said Cody. 

Kyle didn’t leave a lot of specifics on what he wanted to happen after he was gone.  

It was living he was focused on, not dying. 

After his first round of cancer he told his brother and a friend that he had written some notes on what he would like them to do with his kids – hunting, fishing, rodeo … “I can tear that up now, I won’t need it,” he told them. Until the very end, he believed he would beat this again; there was no sense in talking about it. 

But everyone knows what Kyle would want for his kids. 

Elsie, 10, is a “miniature of her father,” said Anna. “She is a leader, a strong personality, all the kids are drawn to her.” Elsie ropes and runs barrels and loves basketball. “She is very talented and super fun,” said Anna. Cleah is 6. “She is loves dresses and makeup and perfume and looking fabulous every day,” said Anna. “She is very sweet and kind; she’ll give you a massage if you’re hurting and doctor you up.” Huckleberry is 3. “He is ALL boy,” said Anna. “He ropes all day long, rides ponies, plays with bulls and works cows. He loves the outdoors.” 

Cody said the memorial service for his brother opened his eyes to a lot of friends Kyle had, that even he didn’t know about. “That group of people there, they are family,” he said. “And every one of them are the same – they’re concerned about Anna and the kids and they are going to be there to help take care of them,” said Cody. 

“Those kids are going to get to do exactly what Kyle wanted them to do and they’re going to know his story.” 

A memorial service was held for Kyle on March 15, 2025, at Miller’s Horse Palace in Billings. The arena was standing room only, with an open bar at the end – in typical Kyle tradition. 

“There was some religion in it, there was some stories in it and when it was over we sat around and drank beer and told Kyle stories and that’s exactly how he would have wanted it,” said Cody. Anna and his family plan to scatter Kyle’s ashes in the Bighorn Mountains, at his wishes. “We will go visit him every summer – our kids love to camp, and that’s how we will spend time with him,” she said.  

Kyle’s dad, Gregg, said they are so thankful for the amount of kindness and support shown to their family during his treatments, and they would like to offer a form of support to other families in need with memorials for Kyle. How that will look will shape out over time.  

Kyle loved adventure – and all of life was an adventure to him, said Gregg. “We’d go on hunting and fishing trips, all sorts of things, and what he really did was make one last good adventure. This is a tough road, but we will go on and there’s a lot of good that is going to come out of it, even if we’re going to miss him a lot. 

“It’s not like he didn’t live a full life. He just had to leave it early.” 

The Kyle Callaway Memorial is scheduled for June 21 at Cottonwood Equestrian Center in Joliet, Montana. Events include an Iron Man (head/heel/steer wrestle), Women’s Triathlon (rope/barrels/goat tie), a 12.5 Slide Team Roping, a 10.5 Slide Team Roping, and Dummy Roping for Kids. For pre-entries, call Cody Callaway: 307-660-3856.