Cordial Competition: Friendly Rivalry Encompasses Jockey Brothers

Jordan and Jake Olesiak don’t like to jockey for position.

When it comes to racing at the North Dakota Horse Park, the Olesiak brothers prefer to keep their competition clean, with a hint of family rivalry.

“We just play around,” Jake said. “It’s fun when you’re racing together.”

The jockeys, from Cloquet, Minn., have become familiar faces this summer at the North Dakota Horse Park.

Jake, 18, is in first place on the NDHP’s jockey money leaders list, while 22-year-old Jordan has the most first-place finishes.

Jordan took over the top spot on the wins list this past weekend when his brother left for two days to compete in races at the Carlton County (Minn.) Fair – the place both brothers began their jockey careers.

Did Jake mind that heading into the weekend that his older brother and mentor would take over his spot?

“It doesn’t bother me at all,” he said with a smile.

After all, bitter rivalry isn’t the nature of the Olesiak family.

“They always try and they’ve always got their head on straight,” horse owner Bud Partridge said. “They ride with nerve.”

Laurie Olesiak usually drives her boys to and from the NDHP and Canterbury Park in Shakopee, Minn.

“I probably wouldn’t be here today if my mom wouldn’t drive us around,” Jordan said. “She drives, we sleep.”

Racing is in the Olesiak’s blood. The brothers began horseback riding on their great-grandfather Wilson House’s farm as soon as they could walk. As soon as they were ready, they wanted to race.

“It was totally their choice,” Laurie said. “It’s all they ever talked about.”

According to their mother, Jake was on his first horse when he was one-and-a-half years old. He took to it like a natural, resting his legs in an upward position associated with many jockeys.

“He automatically did it,” Laurie said. “He was ready to go.”

Now, Jake is a full-time jockey and Jordan splits time between riding and training horses. There’s also two Olesiak brothers who stick to the training aspect of the sport.

Justin Olesiak, 20, trains horses at Canterbury Park and the NDHP but is taking time off after breaking his arm during a training accident.

The eldest Olesiak son, 24-year-old Jesse, is an assistant trainer under longtime Canterbury Park trainer Dave VanWinkel.

“It makes me happy,” Laurie said. “They’re all doing something they like to do.”

With the help of his brothers, Jake is competing with some of the best jockeys in the Midwest.

This summer, the Cromwell (Minn.) High School senior has already won more than $30,000 at NDHP and more than $62,000 at Canterbury Park.

“I’ve had it good,” Jake said. “My brother has taught me everything I know.”

Jordan, who measures 5-foot-8 and 124 pounds, is too heavy to jockey at Canterbury Park. However, he can still compete at the NDHP.

Jordan said he’d like to drop a couple of pounds so he can compete at Canterbury again.

“I’ll get it down,” he said.
Jake is about 5-foot-5 and has kept his weight steady at 113. He isn’t too worried about his size.

“He said he’s not going to abuse his body that way,” Laurie said.

Regardless of how they’re jockey careers turn out, both said they’d like to stay involved with horse racing their entire lives.

“If you love what you do it makes it pretty easy,” Jordan said. “I’ll do it forever.”

Author: Dustin Monke

Former newspaper editor. Now I market the best baked goods and donuts in America. But every once in a while, I write a cool story too.

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