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Opening weekend at the horse races

Opening the horse races
The Olesiak brothers carry on a tradition passed down to them
by John Grones  |  May 17, 2005

I’ll have to admit, I’ve never been to a horse race until this past weekend when I attended the opening of the 2005 season at Canterbury Downs in Shakopee. “Come on down, I’m riding three good horses,” said Jake Olesiak earlier in the week.” He was right, but little did I know, that the best race would be on his brother’s horse, Tricky BooBoo. Then to find out, the horse is trained by their other brother, Jordan.

Not to leave anybody out. I must note that the fourth and oldest Olesiak brother, Jesse, is also working at Canterbury. He was not involved with this particular race because he is the assistant trainer for David Van Winkle, one of the top trainers at Canterbury .

My weekend was quite hectic, but not quite to the level of the four Olesiak boys. It turns out that their day begins around 3:30 to 4:00 a.m., which is about the time they clean stalls, before working with the horses to prepare them for race time.

Race time starts around 1:30 and catching up with the boys is nearly impossible. They did, however, find a few moments to share their passion which was instilled in them by their grandpa, Wilson House.

According to all four boys, horse racing goes back to the Barnum Fair. “My grandpa always had horses at the Carlton County Fair,” said Justin, “and he let us ride them.” The memories at the fair were too numerous to mention, but they all had a couple that stood out. For Jesse, Justin and Jake, it was a race they will never forget.

Jesse, who was riding the gray horse, remembers the day. “I came out of the gate and my saddle came off,” said Jesse. “I was falling off and...”

“I tried to give him a push back on the horse,” said Justin who was racing along-side his brother. “He fell off right over the other side.”

They all still laugh about that story and they all felt that another race in which Two Reasons defeated Pilot Boy was also memorable. According to Jake, Pilot Boy had won three years in a row and Jake was the jockey two of those years. Two Reasons, ridden by Jordan, finally defeated the defending champion.

For Jordan, his most vivid memory was his first attempt at racing. “Sitting in the starting gate balling my eyes out,” said Jordan, who was 11 at the time, “and my uncle Larry made me race anyway.”

Jordan didn’t want to race then, and now that he wants to, he can’t. Last year, Jordan was a jockey at Canterbury and won 14 races. This year, he has switched to training because it is too difficult to make weight all the time. When asked if he was okay with this he hesitated, but said that he was ready to try something different.

At the moment, Jordan is training 15 horses and his number one jockey is his little brother Jake.

Jake, a junior at Cromwell High School, has the perfect build for riding thoroughbreds at Canterbury and possibly the big tracks. “I would like to ride at Churchhill Downs, Keenland, or Santa Anita someday,” said Jake. “Santa Anita is where Seabiscuit used to run.”
Churchhill Downs, of course, is where the Kentucky Derby is run. This year, Canterbury Downs owners opened the track the same day as the running of the Kentucky Derby and they were very pleased with the results. The attendance on Saturday, May 7 was 16,237, which was the largest crowd since re-opening in 1995.

With everything that was going on at Canterbury, Jake and I did have the opportunity to watch the Kentucky Derby in between everything else that was going on. We paid a visit to ‘the Kitchen’, which is located near the stables, to watch the main event. ‘The Kitchen’ is where all the stable employees can relax, get something to eat, and watch television.

Before the race, I asked all the boys who they thought was going to win. Justin, Jordan and Jesse all picked Afleet Alex at 9-2 odds while Jake picked High Fly at 7-1 odds. It was quite a surprise when the horse Giacomo, a 50-1 underdog, won the race. “I’m not surprised,” said Jake. “There are so many long shots every year in the Kentucky Derby, one of them was bound to win.”

It turned out that the winning jockey on Giacomo was Mike Smith who rode at Canturbury for three years in the mid-1980s. He was the track’s leading rider in 1985 and, in 1988, earned his 1,000th victory. He is a member of the track’s Hall of Fame.

After all that excitement, the race that took place on Sunday was still the highlight of the weekend. Jake was going to ride his brother’s horse, Tricky BooBoo, in the third race. Justin, who owns four horses, also works for trainer Kevin Danger. Justin gallops ten horses each morning, in addition to a number of other responsibilities. He would also like to become a farrier.

Justin was pretty excited about the big race and had a few pointers for Jake. “I want him to be patient,” said Justin. “I don’t want mine on the engine. I want him to wait for the right moment to make his move.”

Jordan, who is the horse’s trainer, agreed. “Lay fourth until the quarter pole and see if you can catch the top three.”

The end result was pretty exciting and Tricky BooBoo didn’t exactly take the planned route. “He broke inside right away and we laid second to last,” explained Jake. Tricky BooBoo made his move at the 3/8 pole and caught all but three horses. He finished fourth by a nose. “We just didn’t have enough room to catch them all,” Jake added.

“If the race was a little longer, we might have won,” added Jordan.

The funfilled day was enjoyed by family and friends except for the boys’ father Tim Olesiak. Tim stays back at the ranch near Sawyer to care for the horses that aren’t at the track. “I was planting oats that day,” said Tim. “I’m actually retired. I’m just having a good time.”

Tim shared that he enjoys helping out his four sons and he does get down to the track on occasion. He plans on attending the races the weekend of May 20-21. As for betting? “I just bet small. I always pick wrong.”

Tim may not have had much luck betting on the horses yet, but his luck might change if he bets on another Olesiak hot prospect, Minnesota Bound. “That is the horse I’m waiting to see run,” added Tim.

According to Jake, this horse is owned by Jesse and trained by Jordan. The horse is a three-year-old and is 17-2 hands, which Jake assures me is very tall. Who will be riding Minnesota Bound? Of course, it will be Jake.

He expects to race sometime around the end of June or beginning of July. Sounds like another trip to Canterbury for me. Maybe I’ll bet on a horse this time.

This article first appeared in the May 17, 2005 issue of the Voyageur Press.