“I think he was hanging on for one more go up here in Cairns, if he had of come to the Amatuers this year, that would have been it for him,” Massingham said.
“He loved doing it, he loved coming here as he would ride and then go crabbing and fishing.”
While he was a regular in the north, Thompson also made appearances in South East Queensland, including partnering the Mareeba marvel Paniagua in the 2020 Country Cups Challenge.
The New South Welshman had not ridden the Cairns Cup winner before Mareeba trainer Alex Malliff brought the gun gelding south for the assignment at Doomben, but the stable and connections had their eyes set on one rider.
When contacting the champion hoop to see if he would take the ride on Paniagua in Brisbane, Malliff admits he got a little nervous to ask the legend.
“I am just a bush trainer from North Queensland and I was ringing the most winning jockey in Australian history,” Malliff recalled.
“I was a bit star struck if I am honest but he made me feel at ease as soon as I started talking to him, he is one of us - he is a country boy.
“He is one of the nicest blokes I have met in racing.”
Thompson and Paniagua got the job done in the 2020 Country Cups Challenge Final, winning by two lengths as the favourite.
Malliff, alongside his crew of mates and connections, quickly went from being nervous to chat to the respected hoop to rubbing shoulders together at the Doomben bar.
“It was a good bunch of blokes after we won that race and he fitted right in,” Malliff said.
“He told me later that he enjoyed spending time with the owners and our mates, he said he would love to ride for us again.
“We had plans for him to come up to the Cairns carnival this year but sadly COVID knocked us around a bit, he was pencilled in to ride a few for us.
“He will be sorely missed in the north, he never made mistakes and was so cool.
“He was ferociously competitive as well.”
Having a well-recognised rider like Thompson visit NQ most years developed buzz and excitement within the racing industry and participants loved his presence and guidance.
“He was a champion bloke to deal with, he was a gentleman, that is what he was and still is,” Massingham said.
“When he rode one for you, you knew he would give them every hope.
“You would also get a good guide when he got back from riding for you – he was sometimes telling you something you did not want to hear but he was upfront with and that is what you need.
“Over the years he had a great association with us, he rode a lot of winners for us and then in the latter years, he got on the good horse of ours – Big H.”
In his first few working holidays to NQ, Massingham helped Thompson book his rides before the legend rider struck up a close bond and friendship with the Ryan stable of Ronnie and Janel on the Atherton Tablelands.
The Ryan and Thompson team combined to secure the 2015 Cairns Cup with Seafight and in 2018 they made it two together as We Just Love It stormed down the outside to pinch the crown.
“He has been great for us as a jockey but more so as a person, full stop,” Janel said at the time.
“It is extra special to share this with him and I am sure he feels the same way.”
Ronnie, who is married to trainer Janel after previously riding against Thompson, would often split their time between racing and fishing during his NQ visits.
“Me and Robbie are from our own era,” Ronnie said.
“There are only 12 months between us in age and he is just a special person. He has ridden so many winners for us but he is a gentleman too.”