The first time around, the Melbourne jockey’s two-day licence was a whirlwind visit where everything happened in a blur, and the next thing he knew, he was flying back home with his first ‘black type’ winner under the belt, Mister Yeoh in the Group 2 EW Barker Trophy (1400m) for trainer Cliff Brown.
Short, sweet and definitely career-defining would sum up the hit-and-run. Besides also finishing second aboard Mo Almighty (also trained by Brown) in the Group 3 Saas Fee Stakes (1200m), Thompson also rode at the Dester Singapore Gold Cup meeting two days later, but was less lucky.
The pitstop visit in a country which, like most Australian jockeys, he was widely exposed to, but which was not necessarily a goal on his immediate career path, had suddenly whetted his appetite for more.
And that’s why the second stint is hugely different – the 300-odd race winner had more time to sit back and weigh up his options, and the nod that came is for one year.
“I had only three days to give an answer when Mr Brown rang me the last time,” said Thompson.
“It all happened so quickly. It was a very good opportunity and I had to make the most of it.
“It was all very exciting, very surreal. I came here with an open mind, not knowing what to expect, and it was a lot different to what I’m used to, but it was a very good experience.
“If I had missed that opportunity, I would have regretted it. That’s why I believe everything happens for a reason, and I’m very glad that I came up.
“I came into the unknown, and I can’t believe how lucky I was. The first Group win was a real bonus and a memorable chapter of my riding career.”
At 22, such sudden fame and success at his very first offshore stint could have given him the often deceptive impression Singapore was easy pickings, but the son of champion greyhound trainer Jason Thompson is aware it will be a different ball game this time.
“It was a tough decision to make. On one hand, trainers back home have supported me for four and a half years, and at this stage of my riding career, the next five years are important step-ups,” said Thompson.
“I’ve only been a senior jockey for 10 months. I’ll also be away from my girlfriend Stephanie Thornton, who is also a jockey.
“But I’m sure I’ll be able to fly back home when I get the chance. This was an opportunity I couldn’t possibly miss as I’m sure it will greatly benefit my career.”
The lightweight jockey (he weighs in at 49kgs) only landed in Singapore for his longer-term stay last week, and rode at his first meeting on Sunday. Unfortunately, in five rides, he did not enjoy the same success (all unplaced) as at his flying November debut, but he intends to catch up quickly.
“I’m riding freelance this time. As I already knew Cliff Brown and trainers like Shane Baertschiger who gave me rides last year, they’ve helped me get rides,” said Thompson, who interestingly, was once indentured to former Kranji-based trainer Mick Kent.
“I will be spreading myself around. I’ve got seven or eight different trainers who have supported me so far.
“I’m all up for chasing rides. Back home, I believed in doing things properly and that’s the way it will be here.
“Obviously, I’m still learning about the set-up, the ratings and the way handicaps work here, but I’m confident I will pick them up.
“I’ve got seven rides on Friday and three on Sunday. Hopefully, I can ride a winner this week.”
Thompson is booked on Runminderbinderrun (Stephen Gray), Lucky Master and Special Rain (Alwin Tan), Neo’s Classic (David Kok), Chief Clerk and O’Reilly’s Dancer (Baertschiger) and Black Jade (James Peters) on Friday, and Paparazzi (Tan Kah Soon), Oliver (Baertschiger) and Magnificent Gold (Brown) on Sunday.