'I know she's watching over me': O'Reilly wrestles to honor late mother

Goodhue graduate and Minnesota standout wrestler Bailee O'Reilly has had a lot thrown at him in his life. But he keeps coming back for more, in honor of his late mother. (Photo courtesy of the University of Minnesota)

MINNEAPOLIS – Bailee O’Reilly remembers that dreary day like yesterday.

Sept. 29, 2008. The day his mom died.

Jamie O’Reilly was just 32 years old when she lost her battle with cancer. She was the lone woman in the O’Reilly house. Jamie and her husband Zach had five boys: Bailee, Kaleb, Kelby, Baxter and Maddox.

Bailee was the oldest, and he was just 9 when Jamie died. Maddox was 4.

Five boys. Separated by just five years.


"It was devastating," Bailee said. "We were all so young."

The O’Reilly’s owned a dairy farm in Goodhue, and unfortunately, life didn’t give them any time to breathe. 

They had to just get back to work.

That meant Bailee had to take on a bigger role in his house. While his dad headed out to the farm to get the work done in the mornings, Bailee’s task was getting all of his brothers ready for school and onto the school bus. 

He made sure that everyone was wearing acceptable clothes, that the cold cereal had been eaten and that the homework was in backpacks. Then, the quintet of O’Reilly brothers would bound into the school bus. 

After school, Bailee would make sure that everyone’s homework was done before they went outside to finish their chores. It was a ton of responsibility for a kid who wasn’t even a teenager.

"I was pretty young, so it was definitely hard," O’Reilly said. "I probably don’t give my dad enough credit. He was a full-time farmer and a full-time dad as well. He did a great job, but it was a lot to handle. I had to step up. I took a bigger role early on to take care of my brothers and be a second role model for them." 



After the death of his mom, O’Reilly had to grow up fast. But he was still a kid, and he needed an outlet. Sports became his obsession. O’Reilly wrestled and played football with his brothers in the backyard after they had finished both their chores and homework.

O’Reilly enjoyed football, but he fell in love with wrestling.

Goodhue varsity wrestling coach Josh Grant remembers coming into the first day of practice and watching O’Reilly begin to warm up. O’Reilly was in seventh grade. 

"I must have had my mouth open at one point," Grant said. "He had such intensity; such a work ethic. I told my assistant coach, ‘I think he’s going to be really special.’ It was just a feeling. It sounds too good to be true. But I’ve never said that about anybody else in seventh grade."

Grant believed that O’Reilly was going to be really good one day. But he wasn’t anything special during middle school. Even as a freshman in high school, O’Reilly was average.

But the work ethic that he owned was something that Grant couldn’t teach. It was special. 

Still, the results didn’t immediately manifest. During his sophomore season at Goodhue, O’Reilly went up against Zumbrota-Mazeppa star Caden Steffen. Despite all of the hard work that O’Reilly had put in, Steffen defeated him in a tough, overtime bout. 

O’Reilly realized that he had to work harder. 


Grant showed O’Reilly a tweet where Steffen was spotted running through the snow at 5 a.m. before school. 

So, O’Reilly decided he was going to work just as hard. 

And when O’Reilly makes a goal, he achieves it.

His goal was to qualify for state. So, every day he would get an extra lift in or an extra practice session. 

In a rematch with Steffen, O’Reilly won and qualified for state as a sophomore. 

The next goal was to win a state title. As a junior, O’Reilly did just that. And then he won another state title as a senior.

"He went from not winning a match to not losing a match in the state tournament the next two years," Grant said. "I mean, who does that?"

In his final high school match, O’Reilly clinched the Class A 160-pound championship by outlasting Jackson County Central’s Dalton Wagner for the crown. He finished his high school career with an outstanding record of 151-24.


"He’s always persevered through the bumps on the road, on and off the mat," Grant said. "To me, he’s the definition of a champion."

O’Reilly’s next goal was to wrestle at the Division I level. In typical O’Reilly fashion, he got that done, too.

O’Reilly not only earned a scholarship to the University of Minnesota, but he’s found his way into the starting lineup. He now teams up with Steffen, the man who opened his eyes as a high school sophomore.

The 165-pound redshirt sophomore has gone from a mediocre wrestler in middle school to a starter at a Big Ten program.

"I’m just so lucky to be able to compete and get in the starting lineup," O’Reilly said. "I feel like each week I’ve tried to progress and build off what I’ve done the week before. I feel like I’ve made a ton of improvements from the first dual to the last weekend."

O’Reilly is 18-6 this season for the Gophers. He’s won seven of his last eight bouts, with his only loss coming to Wisconsin star Evan Wick. 

O’Reilly admitted that he’s surprised himself a bit with his meteoric rise. But Grant isn’t shocked to see his former pupil turning into a Big Ten star. 

"No, I’m not surprised at all," Grant said. "Bailee O’Reilly is a warrior. Coaches tell guys what to do all the time. The difference is Bailee always executes (those instructions)."



O’Reilly’s story is one of toughness, determination and heart. He had to grow up so much faster than most after the death of his mother.

He might only be 20, but his Minnesota teammates sometimes refer to him as a "grandpa" because of his maturity.

Don’t let that nickname deceive you. O’Reilly is the most competitive guy on the mat. His goal-setting technique is still alive and well. This time, his goals are even higher. O'Reilly wants to be a national champion. He wants to become an All-American.

But it’s not for his own gain. O’Reilly decided to go to Minnesota because he wanted to be close to his brothers. Because that’s what big brothers do. He’s watched over them. All four of them have their own wrestling careers, and he’s been a steady guiding presence.

A one-hour drive is all that separates O’Reilly from his brothers. Now, he has a 5-year-old sister, Greta, and O'Reilly wants to be a significant part of her life, too.

O'Reilly is a man who puts others ahead of himself. He returns to Goodhue High School to help out Grant's squad whenever he can.

"His perseverance and his resilience through life’s struggles are truly impressive to me," Grant said. "I’m really proud of him."


O'Reilly chooses to serve.

O'Reilly chooses to wrestle for his mom. 

Sept. 29, 2008, is a day that will forever be seared in O’Reilly’s mind. Jamie O’Reilly isn’t here to see Bailee wrestle. But each time he steps onto the mat, he’s furthering her legacy.

"There have been times where I kind of wish she was here and seeing everything that I’m doing," O’Reilly said. "But in my mind, I know she’s watching over me and my brothers. That’s a comforting thing. Even during the toughest times, I think of what she would want me to do, and it’s motivation to train harder, work harder and be a better person the next day than I was before."

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