Dickey Bob, the richest Minnesota-bred quarter horse of all time, will likely make his final start at Canterbury Park on Wednesday in race eight.

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SHAKOPEE, MN–JUNE 17, 2025–Dickey Bob, the richest Minnesota bred quarter horse of all time, will make what is likely his final start at Canterbury Park on Wednesday in race eight.

Trainer Jason Olmstead refers to this as the 10-year-old Dickey Bob’s retirement tour.

"They got this race to go for him," he said of the racing office. "I don’t think there will be anything else for him here this season. I hope he puts on a show and wins."

Dickey Bob was bred in Minnesota by Bruce and Judy Lunderborg who run as Lunderborg LLC. He is by the sire Apollitical Jess out of a mare the couple raced named Paint Or More. Dickey Bob has 14 wins from 22 starts at Canterbury, missing the top three just four times while amassing earnings of $260,695.

He has at least one win and at least one stakes win each season at Canterbury from 2017 through 2023. There were no races for Dickey Bob in Shakopee last year but he ran nine times between Remington Park, Will Rogers Downs and Prairie Meadows, winning twice.

"Last year as a 9-year-old he got out nodded in a Grade 2 at Remington by a hell of a horse," Olmstead said.

In all Dickey Bob has started 68 times with 31 wins, nine seconds and eight thirds with earnings of $512,719. He has won at distances from 110 yards to 400 yards.

"When they don’t lose a step at his age it’s just sheer dumb luck," Olmstead said. "I pride myself in our program and having older horses still running. To have a horse at 10 stay at the same level as when they were 2 and 3 is an accomplishment.

"He takes care of himself around the barn. Doesn’t matter where we took him he always competes."

Paint Or More has produced several full brothers to Dickey Bob including Pyc Jess Bite Mydust who had a stellar career of his own winning seven times and earning $274,662.

For several years the brothers, Bite Mydust is a year older, had epic battles in state bred stakes often taking turns beating each other while running one-two.

Jess Rocket Man, another full brother, was foaled in 2018. He also faced Dickey Bob at Canterbury beating him in the 2022 Bob Morehouse only to have Dickey Bob get the better of him in the Skip Zimmerman later that summer.

When his career does end this year, Dickey Bob will be retired to Olmstead’s Oklahoma farm.

"I’ve got BiteMydust and Rocket Man already," Olmstead said. "There is room in the pasture with them." There is also room in the Canterbury Park Hall of Fame, where Dickey Bob is destined to join his trainer.

Racing begins at 5 p.m. Central on Wednesday.

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