James "Jim" Sayler

Jim Sayler perfectly embodied the old-school definition of a true cowboy—a man with a profound, almost intuitive understanding of a horse’s mind and body. A lifelong, prolific horseman, Jim spent his life bridging the gap between horses and humans, serving as a patient mentor infused with genuine cowboy charm and hospitality. Whether at the barn, trackside, or at home, a fresh cup of coffee was always on, and a warm welcome was always guaranteed.

Jim is deeply loved and remembered by many including his daughter, Jennifer Lynn Sayler Berry, Son in law Rob Crites, Grandon Zac Crites and Jim's longtime partner, Dr. Alyson Harper.

A Lifelong Legacy on the Track

Jim was a deeply respected, elite Thoroughbred racehorse trainer who spent six decades working on the nation's major tracks. He made a formidable name for himself on the highly competitive California racing circuit—including Santa Anita, Hollywood Park, and Del Mar—as well as historic Midwestern tracks like Latonia and River Downs.

His deep connection to horses was woven into his DNA. Growing up on a farm in Wetonka, South Dakota, Jim was one of eleven siblings (six brothers and four sisters) who worked the family land. The boys would herd wild horses to train, sell, and work the fields. It was here, alongside his brothers—including Vernon and Bernie, who became jockeys, and Milbert and Ardell, who also trained—that Jim’s real education was formed. From his very first racing start at the age of 13 in Aberdeen, South Dakota, to his passing at age 77, Jim's entire life was anchored to equine performance.

The All-Around Horseman

While in his twenties, Jim spent his weekends riding in rodeos to fund his racing stock, ultimately becoming a Saddle Bronc Champion in 1981 and 1984. Later in life, at his sister Judy's request, he proudly drove a team of horses pulling a Wells Fargo stagecoach to lead the opening ceremonies for the Professional Rodeo Cowboys Association in Oregon.

In his thirties, he expanded his horizons to "hobby" train hunter-jumpers, successfully conditioning horses for competition at Madison Square Garden. Yet, being inherently shy by nature, Jim ultimately chose the quiet, early morning hours of the racetrack over the roaring spotlight of the rodeo and show arenas.

The Ultimate Teacher

In the racing community, Jim was legendary not just for conditioning winners, but for his masterful knowledge of breaking, preparation, and equine psychology. Hall of Fame jockey Steve Cauthen credits Jim with contributing to his early successes, and legendary riders like Vernon Bush credit Jim with teaching them how to truly ride and handle "every rat that there was" early in their careers. Jim emphasized patience, left-hand stick control, and working with the animal rather than against it. Indeed, Jim’s greatest thrills came from working with difficult, temperamental horses—those deemed "untrainable and uncontrollable." His patience, balance, and understanding were a true gift to the animals he healed and the people he mentored.

Decades of Consistency

Operating a public stable while frequently holding an ownership stake in his runners, Jim trained thousands of horses over the years, logging well over 1,500 career starts and hundreds of victories. He was a meticulous student of breeding and conformation, possessing a rare eye for spotting raw potential and the gentle touch required to build a relationship of trust to bring that potential out on the track. When you look at someone who dedicated every single day of a multi-decade career to the care, mechanics, and spirit of Thoroughbreds, you see a man who found his truest calling in the stables. In the quiet company of horses, Jim found a clear, predictable, and beautiful bond—one that defined his life, inspired his peers, and left behind an indelible mark on the American racetrack.

He has crossed his final finish line, but his legacy rides on.

Family 

Mother Emma Obenauer 1912-1987 age 75

Father Fred Sayler 1908-1980 age 72

Siblings

Milbert Gideon Sayler 1936-2025 age 89

Lloyd Sayler 1938-1951 age 13

Betty Jean Sayler Klein 1940-1995 age 55

Shirley Sayler 1941-1941

Donna Mae Sayler Olsen 1951-

Judy Ann Sayler Wittenberg 1947-

James Fred Sayler 1949-2026 age 77

Vernon Otto Jockey Sayler 1950-1971 age 21

Ardell Sayler 1952-2019 age 67

Bernon Sayler 1957-2020 age 63