Former Trainer Chuck Simon Passes Away At 57

Chuck Simon, who retired from training in 2019 after a 20-year run in which he won 359 races, passed away Sunday at Saratoga Hospital after a bout with cancer. He was 57-years-old.

Before going out on his own, Simon worked for Wayne Lukas, Pete Ferriola, Nick Zito and Tom Skiffington. His mentors included Allen Jerkens. He spent six years with Jerkens working as one of his assistants. He went out on his own in 1999 and five years later gave a job to a young newcomer to the track, Cherie DeVaux.

“Chuck is the whole reason that I am where I'm at this point in my life,” DeVaux said.  “I worked for him early on and I was definitely a crazy early-20 something.  He saw that I was going down the wrong path. He didn't force me to do anything I didn't want to do but he gave me direction and really took me under his wing and gave me guidance. He was almost like a big brother. He has known my family for along time. He got his start in racing working with the harness horses in Saratoga. I really do owe everything in my life with him. He put me on the right path.”

Once news of Simon's illness became public owner Carlo Vaccarezza started a Gofundme page to help cover his medical costs and raised $101,270.

“It's very sad,” Vaccarezza said. “I won the first race today at Kentucky Downs and I dedicated it to Chuck. He was a very dear friend to a lot of people. I had been really good friends with Chuck for many years and we spent a lot of time together. He had been suffering lately.”

Simon grew up in Saratoga Springs and, as a teenager, started working with both the thoroughbreds and standardbreds. He attended the Racetrack Industry Program at the University of Arizona, where he got a BS in Animal Science.  One of his first jobs was at Yonkers Raceway, where he was the assistant racing secretary.

In 1999, he opened a public stable and won 15 races that year. By 2019, Simon was down to just a couple of horses and found it difficult to compete against the super trainers and only won two races that year. He left training and began to host the Going In Circles Podcast. He was also a regular on X, where he wasn't afraid to express his views and never worried about who he might have offended. On the Going In Circles website, there was a section that summed up Simon's attitude and his willingness to go after the types of stories that might have made some people uncomfortable.  “There is no topic too hot for us to handle and no issue that we won't cover,” it read

“He was outspoken,” DeVaux said. “He wasn't afraid to be the bad guy or share a negative opinion. What he ultimately wanted was to make the whole sport better.”

After he left training, he was also hired to oversee the newly created Gulfstream Horsemen's Purchasing Association, a for-profit subsidiary of the Florida Horsemen's Benevolent and Protective Association.

Simon's stable amassed over $11 million in earnings. He trained 19 stakes winners, including two graded winners, Grade III winner Sabellina (Langfuhr) and Grade II winner Battle Won (Honour and Glory).