Chuck Simon, a former trainer who was perhaps best known for his outsized and unsparing presence on social media, died on Sunday at a hospital in Saratoga. Simon, who had recently been diagnosed with cancer, was 57. A former assistant to several Hall of Fame trainers, including D. Wayne Lukas and Nick Zito, Simon carved out a decent career as a trainer from 1999-2019, winning 359 races from 2,679 starts, with purse earnings of $11.2 million. His best years were in the early stages of his career, when he often topped the $1 million mark for earnings, while also dabbling in side projects like a horse lay-up and rehabilitation property in Kentucky. Although his training operation struggled in the 2010s, Simon found a new calling at that time in social media, where he became an outspoken commentator on racing issues. He then launched a podcast, Going in Circles, that discussed racing history and racing controversy in equal measures, often advocating for the issues that most affected workaday horsemen. Simon was a frequent guest on the “At The Races” radio show hosted by Steve Byk. The Monday morning edition of the show had a tribute segment to Simon. “He was a kind and caring guy who cared about the different people involved in racing who loved it and worked hard trying to make a living out of it,” said Jimmy Jerkens, a trainer and the son of one of Simon’s mentors, the Hall of Famer Allen Jerkens, during the tribute. “His beliefs and observations were spot-on in today’s lopsided world of racing.” Byk, who had been friends with Simon for decades, said that Simon could “see around corners” when discussing issues important to racing. “What he understood best were the societal and financial forces facing racing,” Byk said. “He was prescient in so many things we are just now trying to figure out.” Cherie DeVaux, a Kentucky-based trainer who worked for Simon from 2004-2010, said that Simon had put her on the proper path after first coming to the track as an exercise rider in Saratoga Springs. DeVaux went on to become an assistant to Chad Brown before going out on her own in 2018. “I was in my early 20s, and I was a party girl,” DeVaux said. “Chuck put me on the right path. He taught me what to do and how to handle myself and put me on the right path. If it wasn’t for him I wouldn’t be where I am right now, and it probably wouldn’t have been a good path if it wasn’t for him.” DeVaux also credited Simon with teaching her the proper way to manage lower class horses. “We had to really be careful with those horses, because that was all we had,” DeVaux said. “You had to know how to be a horseman, how to manage all the little things.” Simon grew up in Saratoga Springs, where a job in the racing industry is literally just around the corner. Following early work as a teenager at Saratoga’s Thoroughbred and harness tracks, he attended the University of Arizona Race Track Industry Program in Tucson. After working as an assistant in several high-profile New York barns, he went out on his own in 1999. He relocated to Kentucky in the early 2000s. His best horse was Battle Won, a gelding who won the Grade 2 Churchill Downs Handicap in 2005. Simon was diagnosed with metastatic cancer earlier this summer. Carlo Vaccarezza, a horse owner and friend of Simon, led fundraising efforts that raised more than $100,000 for his care. “You were the most amazing person that most of us ever met,” Vaccarezza said in a Sunday social-media post. “You will be forever alive in our hearts and we will miss you more than words can say.” Four tracks are currently planning races this Sunday named in Simon’s honor, according to Byk. The tracks are Aqueduct, Churchill Downs, Gulfstream Park, and Monmouth Park, Byk said. :: Want to learn more about handicapping and wagering? Check out DRF's Handicapping 101 and Wagering 101 pages.