On The Trail with Riley Wakefield

by Siri Stevens

I’ve learned how to win and lose – to deal with adversity – that’s easier said than done. I try to be thankful from the beginning and look failure in the eye.

he first time Riley Wakefield went to the Cinch Timed Event Championships, he and his older brother Brady were star-struck. The next time he attended, 15 years later, he went as a contestant, finishing in fourth place. At the 2023 Cinch TEC, the O’Neill, Neb. cowboy turned in a time of 366 seconds throughout five rounds to finish fourth and win $10,000. After applying for the prestigious event for the past five years, Riley was first on the alternate list this year. He got the call in early February that someone couldn’t make it, and there was a spot for him. He prepared, making four or five runs in each event, every day.
It was in 2008, when Riley was eleven years old, that he and his family, including parents Jim and Susan Wakefield, went to Guthrie’s Lazy E Arena as spectators. “It was a treat,” Riley said. He and Brady saw their heroes among the competitors. “I just remember seeing role models,” he said, “seeing people in places that I wanted to be, people with extreme talent. We had old videotapes of the finals so we knew who guys were, and when they’d walk by us, we’d stare at them. And to see them in person, we were star struck. It was a pretty amazing experience.”
He and Brady, who passed away in a vehicle accident in 2015, got their picture taken with Trevor Brazile.
The CINCH Timed Event Challenge is an invitational event, taking the best twenty cowboys in the world, to compete in five events: steer wrestling, tie-down roping, heading, heeling, and steer roping, in four rounds, with the best fifteen going on to the fifth round. Fastest time in all four events, over five rounds, wins. Riley was leading the average going into the fifth round but a sixty second run in the team roping put him in fourth place for the finish.
A 2020 graduate of Northwestern Oklahoma State in Alva, Riley has been living in Stephenville, Texas. But this winter, he was at home on his parents’ (Jim & Susan) ranch near O’Neill, during what was the worst winter in the last ten years in north-central Nebraska; O’Neill has had 57 inches of snow. The snow and cold weather made everything harder to accomplish. “We had three feet of snow on the ground, and it was an absolute workout to get to the horses. You had to lift each leg through the snow.” All the watering was done by hand, because the tanks would freeze to the bottom by morning. “We hand watered everything,” he said. Riley’s girlfriend Jenna Dallyn helped him, loading cattle, roping with him, until she had to return to High River, Alberta, to work. Then his dad helped. Jim “was out there every day, all day, pushing cattle. When Jenna left, he had to fill in and be the guy to help me. He was a huge part of this.”
Cinch TEC contestants designate “helpers,” who head, heel and haze for them. Cinch TEC contestants cannot head or heel for each other, but they can haze for each other. Riley’s header was CJ DeForest; his heeler was Tanner Braden, and Allen Good was his hazer for three rounds with Mason Couch for the last two rounds. Nerves wore on him for round number one, which showed up in the heading. “That first head loop I threw, it was not a good head loop but a nervous head loop. It was sloppy,” he said. “I was feeling the nerves.” But when the tie-down roping came around, he settled in. “As soon as I tied my first calf, I felt a lot more comfortable. The set-up fit my horse perfectly. He has a lot of run, he’s fairly free, and he doesn’t take my shot away.”
In February, after getting the call that he would be competing at the Cinch TEC, Riley was nervous. The event was so important to him, the concept of being a “true” cowboy and showing skills across four disciplines, had him anxious. So nervous, that he’d never felt this much nerves since he and Brady backed into the box at the 2012 National High School Finals Rodeo, when he was a freshman. The brothers had done some mental training, with one of the pieces of advice being that they should visualize the best thing that could happen and the worst thing that could happen. It worked; he and Brady finished as reserve team roping champions that year.
So Riley applied the same concept to the Cinch TEC. He knew, if he failed, that he’d still have family and friends who still cared about him, and he could still have the chance of being invited to compete at next year’s Cinch TEC. “After I looked failure dead in the eyes,” he said on a Facebook post, “the rest of the Cinch TEC was pretty smooth sailing.”
He grew up on the family ranch south of O’Neill, in the Sandhills of Nebraska, with a dad who was a pro steer wrestler and roper.
When family friends came over to the Wakefields to rope, it was Brady and Riley running the chutes, and looking up with respect to the men who practiced with their dad.
“It was an honor to ride their horses around after practice.”
Like many young cowboys, they fell in love with the sport. Jim and Susan hauled their boys to Little Britches Rodeos and youth events all over the region.
The brothers loved it, Riley said. “We took a liking to it and got small successes along the way, that keep you going, and sooner or later, you get bigger successes, then bigger and bigger, and by that time, we were hooked.”
In junior high, Riley wanted to be a bull rider. He followed the PBR faithfully and got on roping steers at home. But in eighth grade, he realized the timed events were more his thing.
In high school, he qualified for state finals and the National High School Finals all four years, competing at Nationals four times in the team roping and once in the steer wrestling.
In college at Gillette (Wyo.) College, he made it to the College National Finals Rodeo in 2017 in three events, then two years later, won the tie-down in the Central Plains Region while a student at Northwestern Oklahoma State.
Riley rode his horse Gator for the tie-down roping and his horse William for the heeling, borrowing horses for the other three events. Gator has been a long-time project for the cowboy. When Riley’s horse died of colic three years ago, friend Austin Barstow suggested that Riley borrow Gator, who showed potential but was really green. “I knew from the start that Gator had tremendous ability and athleticism,” he said. “But he is extremely playful. He is difficult to catch, he messes around, and he sees how much he can get away with. That’s been the struggle, to get the business attitude out of him.”
At a rodeo in 2021, after Riley roped a calf, Gator misbehaved, stepping away from him as he tried to re-mount. “It took me a full minute to get on him. He was inching away from me in a circle. He wasn’t dragging the calf, but he was moving away.” A few weeks after that, Riley took him to the Badlands Circuit Finals Rodeo, where he worried how the horse would respond to an indoor arena with noise and lots of activity. “I was nervous and had no idea what he would do, but the circuit finals was a turning point. He worked better than he ever had, in a loud and pressure-filled environment.” The twelve-year-old bay has improved. “He’s more business-like now, and I think we’ve both grown up together. I’ve learned how to train one and ride one correctly, and that’s more important than a lot of people understand. A horse is sometimes only as good as his rider.”
For the steer tripping, he rode Todd Eberle’s horse Mississippi, and for the heading, he rode Danielle Wray’s horse, Peanut. Danielle was instrumental in helping him in 2021 when he qualified for the Badlands Circuit Finals Rodeo in three events, and at the Cinch TEC as well. “I couldn’t have done either without her.”
Riley, at age 26, is working at making rodeo his fulltime job. It’s not easy. Last year, he competed across the nation, at times broke and trying to prove himself, not only to the rodeo world, but to himself. “I went through some hard times, really low times,” he said. “I questioned why the heck I was doing this. I have my (college) degree, why am I not at home, working, making for-sure money.” He remembers tough times last summer, traveling in a small trailer with a shower, no bathroom, and two bunk beds, and the time in Caldwell when his traveling partner headed to another rodeo but Riley stayed for the short round. From 6 am, when his buddy got on the road, till 4 pm, when a friend arrived, he sat on the grounds with his lawn chair and phone, while Gator grazed, “taking it all in.”
Rodeoing isn’t cheap, either, with entry fees and fuel bills. “You pull the trigger anyways,” he said. “You can’t be emotional about (spending) the money. You have to trust your talent. If you worry about the money, you’re going to be worried all the time.” During the hard times, he talked to his dad, telling him he was ready to come home. “I remember calling my dad, and he said, ‘you chose to do this, you’re going to stay on the road.”
It can be a game of confidence, Riley said. “When you’re new on the trail, you feel like you have something to prove. You feel like you’re not trying to lose, instead of trying to win, not looking like an idiot, instead of going out there and wining first.
The fourth place finish at the Cinch TEC has boosted his confidence. Now, when backing into the box, “I’m thinking about how fast I can be instead of how not to mess up. I’m thinking of what can go right instead of what can go wrong.”
His parents are behind him one hundred percent. “If I didn’t have my parents helping me out, I would be working a nine-to-five,” he said. “My wins are just as much theirs as they are mine. We’re a team.”
This summer, he will rodeo full time, competing at 80 rodeos, heading to California in April, with a bounce in his step and more confidence under the cowboy hat.
Rodeo hasn’t always come easy to him. “I wasn’t one of those guys that was consistently winning,” he said. “It took some things I needed to work through.”
There were several times he could have quit, but he didn’t. “To me, it’s the fact that I put all the work in and I didn’t want to waste it. I wanted it to pay off somehow.”
“I felt like I could have decided to teach school, forget about rodeo and make some money. I could have, and I’ve had ended up OK. But I had the opportunity (to rodeo) and I have so many people behind me, and it’s what I love to do and what I’ve worked for, so why not let it pay off? And if it doesn’t, that’s fine, but I want to give it the chance.”
His hard work and perseverance is yielding a profit. “I’m so glad it’s paying off now. There’s nothing better than hard work paying off.”
Riley credits his sponsors with helping him stay on the rodeo road. They are Rattler, Wrangler, Wakefield Insurance Agency, Pritchett Twine and Net Wrap, Laursen Chiropractic, Twin Creek Ranches, and Make An Impact.
Cody Doescher won the 2023 Cinch TEC with a time of 312.7 seconds (total on 25 head); Russell Cardoza was second (321.7 seconds); Lane Karney was third (355.3 seconds.)

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