A well-known Sydney transport veteran is set to retire after 46 years behind the wheel, putting his full fleet to auction through Pickles.
After nearly half a century as a truck driver and operator, Ashley O’Connor is calling time on his career and putting his multi-million-dollar fleet under the hammer.
Ashley’s story is one deeply woven into Australia’s transport industry. The son of a truck driver, he was behind the wheel from the age of eight, hauling hay on the family farm.
By 18 he’d bought his first truck, and within two decades he’d grown from subcontracting runs to running one of Sydney’s largest family fleets. At its peak, the business boasted 42 trucks and 73 trailers.
“I just loved driving – seeing the country, building up the fleet and having good people around me,” Ashley says.
“Over the years I’ve been fortunate to give a lot of drivers and their families a good living, and that’s what I’m most proud of.”
The full fleet from O’Connor Haulage will be sold through Pickles, with the sale set to go live in September before the official auction on October 14-16.
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“Ashley’s fleet is one of the most comprehensive packages we’ve seen in recent years, and it’s a rare opportunity for buyers to secure well-maintained transport assets in one go,” Pickles sales executive Peter Best says.
“We’re proud to be helping him mark the next chapter after such a significant career.”
Ashley admits stepping back won’t be easy. He knows every truck in his fleet by heart – from kilometres to VIN numbers – and plans to keep one truck and trailer to restore and drive for fun.
“I’ll never stop loving trucks,” he says.
“I’ll tinker with one, bling it up, maybe do the odd run, but mostly I’ll spend more time with mates and go fishing with my brother down at Batemans Bay.”
Reflecting on nearly five decades in transport, Ashley has seen sweeping change – from over-regulation to trucks becoming too complicated to fix without computers.
But he says the simple pleasures have stayed the same: the road, the country, and the people.
The fleet auction will be hosted online at Pickles.com.au, with inspections available by appointment.
For trucks and trailers, the auction will start at 10am AEDT on October 14 and close at 6.30pm AEDT on October 16.
For workshop and general good equipment, the auction gets underway at 9am AEDT on October 14 and closes at 7pm on October 16.
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