CV’s Robert Hess, the Original Horse Whisperer

Robert Hess, Jr.

Growing up, Robert Hess, Jr. had two ambitions: to play baseball as long as he could and then become a racehorse trainer like his father. 

He played baseball—and played it well—until a shoulder injury cut short his career after one season at Stanford.  But he’s still training thoroughbreds, and his accomplishments at the track have earned him election into the Castro Valley Sports Hall of Fame. 

Hess idolized his father, the late Robert Hess, Sr., who was still training horses at 86 years old when the COVID-19 epidemic spread through Golden Gate Fields and took his life in 2020. 

“When other kids were going out, I’d go to bed early so I could get up at 4:30 a.m. and go to the track with my dad,” Hess said by phone from Santa Anita, where most of his horses reside.  “The best part was just being with my dad, learning from him.  Being with the horses, learning what makes them tick.” 

Beginning in the summer of 1983, when he graduated from Moreau High, the younger Hess took a few of his father’s horses to race at Del Mar, near San Diego.  His father would stay in Northern California to run horses on the summer fair circuit.

“I got to meet people, get my feet wet,” Hess said. “[My father] wouldn’t tell me anything. If I had a question, I’d call him. Otherwise, he’d leave me alone.  It was baptism by fire.”

Those summers at Del Mar soon paid dividends.  The day after his graduation from Stanford in 1987 and just $700 cash in his pocket, Hess drove his truck and trailer to Hollywood Park and began training under his own name. 

“My first two starters were at Hollywood Park on July 4, 1987,” Hess recalled.  “One finished last, and the other didn’t finish the race.  Not an auspicious beginning.” 

However, his fortunes soon changed; by the 1990s, he was winning leading trainer titles at Hollywood and Del Mar, and his horses were regularly earning more than $1 million per year, often more than $2 million. He had made it in the big leagues of thoroughbred horse racing. 

Many of Hess’s victories have come in partnership with Hall of Fame jockey Kent Desormeaux, a union that began early in their careers on a tip by a racetrack character named Tad Dowd.  “Tad was a character from right out of old-school racetrack movies,” Hess said.  “He always wore seersucker suits and a straw hat—a real character.” 

Dowd told the young Hess about Desormeaux, who was riding in Maryland at the time.  The two met when Desormeaux came to California and struck up an immediate friendship.  Desormeaux has been aboard almost 40 percent of Hess’s winners. 

A multiple graded stakes winning trainer, Hess has developed many outstanding horses, including Grade One stakes winners River Special and D’wildcat. But perhaps his favorite was a $40,000 claimer named Slerp, who went on to earn more than $600,000.   

“He only lost one photo finish,” Hess said. “He had a great brain and a heart of gold.  He loved his job. He reminded me of (San Francisco 49er running back) Christian McCaffrey.” 

With almost 1,500 trips to the Winner’s Circle and nearly $52 million in career earnings, Hess still remembers his Castro Valley roots and the lessons he learned from his father.

“My dad was a man of integrity in a sport where there can be question marks,” he said.  “He was always true to himself and true to the athlete.”  Then he added, “And my mom doesn’t get enough credit.  She was always there in the trenches with us.”

Hess’s stable currently includes 35 horses at Santa Anita and 20 at Gulfstream in Florida.  He frequently travels back and forth but keeps his home in Arcadia.  Hess has two adult sons, Garrison and Christian. 

This is the ninth in a series of 16 articles profiling the 2024 inductees into the Castro Valley Sports Hall of Fame.  The Hall of Fame ceremonies and banquet will be held Sunday, April 21, at Redwood Canyon Golf Course.  For tickets, go to castrovalleysportsfoundation.org and click on “Events, Hall of Fame Banquet.”