It was the 2001 derby where he and his pit crew (dad) picked up the big spot prize of the day as well as the overall win.
"I got $250 which was pretty amazing when you're only eight," he said.
"Mum made me put it into my primary school bank account."
And the following year, with only minor tweaks to the kart made simply of wood, with four basic wheels, no brakes and ropes to steer it, triumphed again ... and the following year.
"It was all pretty basic back then - no brakes or anything so you had five or six people at the end of the stretch who'd jump in to stop you ... and if they didn't you'd smash into the hay bales."
It was his dad's idea to build the kart for the derby but when it came to hiring the driver his initial choice backed off ... for sartorial reasons.
"My older brother refused to dress up in art deco so I said 'sweet ... I'll do it'."
And the rest was soap box derby history.
A hat-trick of wins for the three years.
He was modest about his ability, given he almost ran into a roadside cone in his first race because he was so nervous.
"Dad was a good push-starter."
He said that since hanging up the racing helmet he had continued to watch the derbies with interest, and particularly how sophisticated some of the karts had become.
"But there are still the basic ones - it's a great mix and no wonder it pulls in a big crowd."
Mr Pickering said there would be a slight change to the start of this year's event with the three main sponsors, Tremains, Gemco and Brebner Print all competing in a special donation race.
Each, along with the Art Deco Trust, had put $500 into the winning kitty, and the three sponsors had all picked a cause to donate the resulting $2000 to should they win.
Tremains have nominated the U-Turn Trust, Gemco the Project Prima Volta and Brebner Print the Hawke's Bay Rescue Helicopter.
After that opening race the competition would be on for one and all, and Mr Pickering was confident the entry list would echo last year's when about 40 karts fronted up.
People wanting to put a kart and young driver on to the traditional sloping Tennyson St grid on the Sunday of the festival weekend can check out the details on the trust's website.
Mr Jackson would not be entering again but was delighted to be part of the organising and promoting team.
"I don't think I could fit in a kart anymore."