Mana Thaugland waited until the women were at their most vulnerable - alone and unaware - then he struck, catching them by surprise to snatch their bags.
The five women were stunned, unable to respond and lost priceless possessions among the thousands of dollars worth of other items.
But the 23-year-old man didn't care, he just tossed the precious belongings out because they weren't valuable to him and he needed money for motels because he was homeless, a court has heard.
On December 16 at the North Shore District Court, Thaugland was jailed for 24 months and ordered to pay $10,000 in reparations after his release for his spate of bag snatches from women shopping at a mall.
He admitted the offending at an earlier appearance.
After reading a summary of events, Judge Lawrence Hinton said "it was absolutely outrageous offending".
"Your targets were deliberately chosen as, and they were, vulnerable. You wanted no opposition. You had to surprise. You chose women on their own.
"They were unsuspecting and stunned by your actions. They were unable to respond. Your offending was planned and deliberate. There was significant loss - you did not care that you might be taking precious personal items and destroying memories.
"You cast away as worthless items that constituted priceless personal history in some cases."
The court heard how in May, Thaugland's first victim had got into her car in the carpark at Glenfield Mall and placed her bag on the back seat of the car before he opened the door, grabbed the bag and ran off.
Then, not 45 minutes later, he used the woman's Eftpos card to buy cigarettes.
That woman estimated she lost $5606 in valuables.
Over the next week, Thaugland targeted three other women - first snatching a bag from a trolley, then grabbing another handbag when it was placed it on the ground.
He later waited until his fourth victim got into her car and placed the bag on the passenger seat - then he opened the door and grabbed the bag.
On June 18, another woman was sitting in her car outside Glenfield Leisure Centre with her handbag on her lap.
Thaugland opened the passenger-side door, reached over and grabbed the bag and ran off.
The victim, a Chinese woman who's been living in Auckland for 15 years, said she'd lost $7400, including a $5000 precious gift "and I loved it dearly".
"I love this beautiful country and always believed it was safe here but I do not feel the same any more. The daylight robbery has changed my life in a bad way," she said in her victim impact statement.
Another woman said she still woke up at night, remembering what happened, because she was also suffering post-traumatic stress disorder from an accident.
"I'm scared of entering any public carparks. I feel not safe living in Auckland any more which is very sad. When the doorbell rings I panic - I'm afraid of theft coming to my house," she said in her statement.
A different woman described losing a special memento of her grandfather and a charm bracelet, while one woman said she'd saved $800 for her son and was set to deposit it the day her bag was taken.
Thaugland's explanation was that he was homeless and needed money for motels.
Hinton called it "outrageous offending".
"This is a very serious business. These were women you preyed upon and stung when they were going about their shopping.
"These people were all surprised whilst they had their shopping baskets, in some cases some of your targets have put their bag down beside them on the seat [of their car] and you reached in and taken it and run off."
The court also heard how Thaugland was caught on his third drink-driving offence after he crashed into another car, writing it off.
Thaugland was sentenced to 24 months imprisonment for the bag snatches, two months for the excessive breath alcohol charge, one month for breaching community work and one month for wilful damage - all to be served concurrently.
He was also ordered to pay $10,000 to his victims over three years after his release.
A spate of bag snatches:
May 23 - a woman placed her handbag on the back seat of her car at the mall. Thaugland opened the door, grabbed the handbag and ran away. Amount lost: $5600.
May 25 - a woman placed her handbag in her trolley as she unloaded her shopping. Thaugland ran up and took the bag. Amount lost: $1000.
May 29 - a woman placed her handbag down on the ground, Thaugland ran up behind her, snatched it and ran away. Amount lost: $1040.
June 1 - a woman got into driver's seat of her car, placed handbag in the front passenger seat next to her. Thaugland came up to the car, opened the door, grabbed the handbag and ran off. Amount lost: $7400.
June 18 - a woman was sitting in her car outside Glenfield leisure centre with her handbag on her lap, Thaugland opened the passenger-side door, reached over and grabbed the bag and ran off. Amount lost: $2820.