Sixteen-year-old Ryder Olmstead earns his first. stakes victory aboard Sheza A Sugar Momma in the North Star State Futurity at Canterbury Park.

@ Coady Media

By Leann Noguera, StallioneSearch

SHAKOPEE, MN–JUNE 20, 2026–Horse racing careers are often measured in milestones. For 16-year-old Ryder Olmstead, two significant achievements arrived just one week apart.

On June 8 at Prairie Meadows, he celebrated his first victory aboard Flyin Cowgirl 123, a horse trained by his father, former jockey Jason Olmstead. The win came on the same afternoon Cody Smith, one of Ryder's longtime favorite jockeys, recorded the 1,000th victory of his career.

One week later, on June 18 at Canterbury Park, Ryder returned to the winner's circle after guiding Sheza A Sugar Momma to victory in the North Star State Futurity for his first stakes win.

The accomplishment carried added meaning for the family, as the filly is sired by Hes Relentless, a horse connected to some of Ryder's earliest recollections at the racetrack.

Among the family's cherished memories is an image of Ryder, as a three-year-old boy sitting proudly atop the future AQHA Racing Champion and leading sire. Years later, his first stakes victory would come aboard one of the stallion's daughters, creating a connection that felt especially meaningful for those who have watched him grow up around the sport.

Ryder Olmstead earned the first stakes victory of his career aboard Sheza A Sugar Momma in the June 18 North Star State Futurity at Canterbury Park,© Coady Media

Sheza A Sugar Momma wasted little time taking control of the 300-yard futurity. The filly moved to the front shortly after the start and steadily widened her advantage before crossing the finish line two lengths clear of her rivals. Covering the distance in :15.997, she gave Olmstead his first taste of stakes success.

Owned by Tom Maher and Paul Luedemann, Sheza A Sugar Momma improved her record to two starts with a win and a second while increasing her earnings to $18,761. Bred by Summer Run Inc., the filly is out of the PYC Paint Your Wagon mare Candy Coated Paint.

The memorable evening did not end there.

Just one race later, Olmstead added another black-type placing when Sophey finished third in the North Star State Derby.

Also trained by his father, Jason Olmstead, for owner-breeder Lunderborg LLC, Sophey raced prominently throughout and stayed on well to secure the show position.

Out of the Moonin The Eagle mare Sweet Corol Line, the filly has now earned $20,899. Her accomplishments also include a second-place finish in the Minnesota Futurity and a third-place finish in the North Star State Futurity.

For Ryder, the evening served as another reminder of how quickly opportunities can develop in racing. Seven days earlier, he was celebrating the first win of his career. A week later, he was walking into the winner's circle after a futurity victory and adding another stakes placing before the night was over.

Adding another layer to the story is the fact that both victories of Ryder's young career have come aboard horses trained by his father.

Through 31 career mounts, he has recorded two wins, eight top-three finishes, and more than $50,000 in earnings.

The evening also brought things full circle for the Olmstead family.

Ryder Olmstead celebrates his first career stakes victory, joined in the winner's circle by his parents, trainer Jason Olmstead and Amber Olmstead. © Coady Media

Following his first career victory at Prairie Meadows, Ryder said he had hoped his first win would come for his parents because they had always been by his side and encouraged him to be his best. One week later, he was once again celebrating in the winner's circle aboard a horse trained by his father.

Through just 31 career mounts, Olmstead has already recorded two wins, eight top-three finishes, and more than $50,000 in earnings.

Only seven days separated his first trip to the winner's circle from his first stakes victory. For a teenager who has spent much of his life around the racetrack, it was a week filled with milestones and memories, and one that may prove to be only the beginning.

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