The next day, he was back and in more audacious mood.
Macgregor put four more bottles of the top-end alcohol into a bag, placed his jacket over the bag and slipped out again.
Church Road chief wine maker Chris Scott described the vintage in glowing terms.
"Merlot takes the lead in the blend this year with its plush mid-palate texture anchoring the wine and defining the character, while the cabernet sauvignon brings it complex aromatics and framework that reins the merlot in and keeping the blend serious and structured."
According to websites, it is advisable to drink it any time between 2020 and 2034.
But Macgregor was not planning to stow it in the cellar.
He told police he had taken that particular wine "as he knew they were expensive and that he could on-sell to make easy money".
It was not just alcohol the defendant targeted.
Macgregor stole a pack of pregnancy vitamin tablets priced at $90, a speaker priced at $279 and two pairs of prescription spectacles priced at $828.
All were taken from downtown Dunedin shops from April to June.
When Macgregor pleaded guilty, he convinced the court he could be trusted on bail.
But more charges arose.
He was caught stealing "a personal groomer" from Farmers while trespassed from the store and even managed to outdo himself at the supermarket.
It emerged that on June 12, Macgregor had swiped a $270 bottle of Dom Perignon before he had turned his attention to red wine.
Judge Kevin Phillips described the man as "a recidivist thief".
"This is what you do ... and you do it badly because you keep getting caught," he said.
Considering the variety of items, the judge said he believed Macgregor was stealing to order.
The defendant had been to jail in the past but his thieving had been "relentless", Judge Phillips said.
Macgregor was sentenced to 11 months imprisonment and ordered to repay $1362.
