Alma senior Sheppard Osborn perseveres despite the loss of his mom, close friends

By Kevin Taylor

Alma Schools 

The smile never changes. His upbeat, masterclass in kindness, empathy, and quiet power is usually reserved for people twice his age. 

But that doesn’t mean Sheppard Osborn is always having a great day. 

Behind the curtain, the pain sometimes persists. 

Last week, his late mom, Cassie Osborn, would have celebrated her 42nd birthday. The day after, as spring-like temperatures reached 75 on the Alma baseball diamond, Sheppard Osborn’s eyes began to mist. 

"That was devastating," he said. "Growing up as a little kid, you look up to her, and you give her hugs — and then your world gets shattered."

Osborn’s parents, Nathan and Cassie, served in the 188th Wing Air National Guard. Nathan served 18 years and did five tours of duty overseas. Cassie did one as well. 

"My mom and dad were Air National Guard out of the 188th,” Osborn said. “My dad served 18 years; he did five tours overseas at various places. My mom did one in Afghanistan. That takes a toll on a little kid being away from your parents because that's an 18-month tour."

Sheppard was only 9 when Cassie passed away on Jan. 11, 2016. He was a third-grader in Van Buren at the time. “We moved to Alma halfway through my fourth-grade year,” he said. 

He never left. 

But the pain wouldn’t end with Cassie’s passing. 

"I was in third grade when she passed away, and I moved to Alma in fourth grade, and one of my best friends, Blaine Williams, passed away in the fifth grade,” Osborn said. “He was the first friend I ever made at Alma."

A three-year starter for the Airedales’ baseball team, Osborn and Alma teammate Cash Wilson befriended Williams in the spring of 2017. 

A year later, he was gone.

Then last August, Osborn’s best friend, Matthew Carter, passed away suddenly. 

"I give you a view of the world not many kids have," Sheppard said. "You mature so much faster, and you're so much more thankful for what you have. When people get mad at their mom and dad for having to do chores or argue over something stupid, it kind of eats at you a little bit.

"They don't realize some kids don't get to go home to see their parents.”

“Sheppard is a prime example of how to handle adversity,” Alma baseball coach Brian Fry said.”He sliced his finger open (last week), got three stitches, and still made the bus ride to Ozark — all with a smile on his face to be here supporting his team. He can find something positive out of almost any situation, and when you think about those tragic events in his life, you know he was raised right and had a tremendous support staff along the way.” 

Sheppard was expected to be out of action for 10 days; he missed time in 2024 because of a hand injury. 

"It's a give and take," he said. "Sometimes, kids want a break, but when you get that break, you realize how much you miss it. I got hit in the back of the hand in the first inning against Siloam. We had just back-picked the leadoff runner, and that set the tone for the game, but the next pitch, I got too close and got smacked in the back of the hand, and I missed two or three games."

College cheerleader

Four years ago, Osborn likely saw himself playing football and baseball in high school. But nagging injuries cut short his football career, and when one door closed, another opened. 

Trey Bowen became the school’s first ‘Airedale Muscle’ back in the 2019-20 school year while in middle school. It wasn’t until his sophomore year, 2021-22, that more boys signed on. 

Last spring, Osborn and several football and baseball players tried out.  

“From the moment I first saw Sheppard stunt, I knew he had the potential to excel as a collegiate cheerleader,” Alma cheer coach Law said. “His raw talent, exceptional coachability, and relentless drive to improve set him apart. He has attended numerous college recruiting clinics and was highly sought after by many schools. I’m thrilled that he has found a home with UCA, and I can’t wait to see him cheer at UCA football games this fall.”

“I’m not surprised that he is going to UCA to cheer,” Fry said. “When he talked about joining, you knew immediately he had a passion for it and he would always get excited talking about what they are doing now and where they are going next. He had a lot of irons in the fire with both sports, but he had the discipline to make it work and earn himself a Division I scholarship.”

Last week, as the Airedales were wrapping up a quick baseball practice, Sheppard sprinted toward the auxiliary gym to work with incoming cheerleaders. 

“Sheppard is a natural leader who leads by example with kindness, encouragement, and unwavering politeness,” Law said. “He consistently gives 100 percent, and always strives to do the right thing, making him one of the most outstanding students I’ve ever met.”

Playoff drought  

Back in the early 2000s, the Airedales routinely made state playoff appearances, including the 2002 state title team. 

Since 1996, the 5A-West has produced 11 state champions. Currently, seven of the eight 5A-West teams have won at least one state championship (all but Siloam Springs).

After back-to-back 4-10 finishes, Osborn believes the Airedales have the experience to punch their first playoff ticket since 2016. 

The Airedales dropped their opening series to Greenwood but return to conference play March 31 against Siloam Springs. 

"There's pressure for everything," he said. "Every spot is up for grabs. There are so many athletes coming through, and that's a wonderful thing. This program hit a dry spot; you had so many athletes come through, and then it just trickled down. And now, we're in the weight room, we're rehabbing correctly, and we're taking care of the stuff we haven't been great about. We're instilling stuff we couldn't handle last year. 

"This year, we want to be perfect every time."

New format

The Airedales haven’t won six conference games in a season since 2016. The last four seasons have produced just 12 league wins, including four in 2023-24. 

But the roster, and level of play, have steadily improved. 

"My freshman year, you had Logan (Taylor), who took everybody under their wing, but my sophomore year, you had (Noah) Likens, (Derek) Hatcher, (Caden) Nesbitt, (Axl) Spain, and (Nathan) Macken — they all took everybody under their wing," Osborn said. "I was grateful for that; they were selfless and gave up reps for us to be able to learn.

"Last year, we had two (seniors), (Branson) Brogan and (Colby) Kimmons."

Alma dropped its 5A-West opener to Greenwood this week. But playing at home, at least once in every series, may balance things out. 

This year, as opposed to the older format of playing doubleheaders, 5A-West coaches opted for the two-day, home-and-home schedule. 

"As a catcher, I love it," Sheppard said. "As a catcher, as far as being hard on your body, I think seven innings and being able to go home and stretch and just rehabilitate makes it better."