Carlton "Jerry" Cunningham's storybook start to his training career, which began on Saturday, May 13, 2023 as one of 39 new licensed trainers, was shattered when his first starter Duke of Springs won but was later disqualified by the race day stewards.

The stewards found that the Duke of Springs interfered with Devonte. The race was awarded to second by the post Master of Hall at odds of 28-1.

Putting the obvious disappointment behind him, Cunningham smiled again, as on May 22 jockey Anthony Thomas produced one of his notable performances in the saddle atop Nina Dorada to win the second of nine races on the day, giving Cunningham his first official winner.

From three furlongs (600m) out of the five-and-a-half furlong (1,100m) contest, Nina Dorada was embroiled in a heated duel with Sir Frederick (Dane Dawkins). In a thrilling, straight battle, Thomas prevailed by a head over Sir Frederick on Nina Dorada.

"I wasn't perturbed by the disqualification. I felt a bit justified because I did have some programmes coming up, which is now, and I know we'll be back in the winners' enclosure in a week, so I wasn't bothered by it. I simply accepted it [disqualification] with humility and moved on. It feels great to have won my first race with Nina Dorada," Cunningham said.

Cunningham stated that now that his win is over and done with, he expects to continue and win additional races because of the mindset he has for the job ahead.

"I currently have eight horses and expect to acquire more. With God's help, I expect to win a lot more races because I know the hard effort you put in will pay off, and I am a person with a strong work ethic when it comes to my horses, so you can expect wonderful things from me in the future.

Cunningham then spoke about his entry into the racing industry.

"From a young age, my father used to take me to the racetrack, and it was there that I fell in love with horses, and I haven't looked back since. My mother would tell my father to stop transporting me to the racetrack, but he continued to do so. When my father said, son, get in the car," he added, "I was in the car before he could say car, and whenever we were about to leave the stables, I cried because I didn't want to leave the horses."