He went from jobless to a winner to a weeper - in six months.
He was down when he was retrenched, soared when he won almost $390,000 in the Toto lottery, and is now down again with less than $200 left in his bank account.
Has the curse of the lottery windfall found another victim in Mr Chew?
For an unusually high number of lottery winners around the world, quick money has not brought them sudden happiness.
Mr Chew was in the dumps when he was retrenched from his job as a warehouse supervisor last November, after 10 years on the job.
He was earning $3,000 a month, and received $34,000 on retrenchment.
Barely a month later, Lady Luck smiled on him - he struck big, scoring with an own entry 'system roll' Toto bet.
His winnings: $383,945.
Now, fast forward barely six months later and he is almost broke.
How did he blow it all so quickly?
He was ecstatic when he first hit the jackpot. He doled out large chunks of cash of up to $100,000 to his family and relatives.
Another big-ticket item was a five-day family vacation to Thailand in January. This set him back by about $10,000.
Another $120,000 was lavished on items such as expensive meals at posh restaurants for his family and friends, and pricey exotic health products such as bird's nest.
Then there was greed: Extravagant, perhaps reckless bets on horse racing and soccer.
Perhaps the only wise move he made was to pay off the $78,000 mortgage on his four-room Housing Board flat in Choa Chu Kang.
While Mr Chew isn't exactly a pauper now, he had 'about $200 or less' in his bank account at the end of last month.
He now does some part-time work in a transportation company, which will earn him up to $1,000 a month, but is on the lookout for a full-time job.
He falls back financially on his wife, 50, a part-time sales person who has some savings. And he hopes to get back a $50,000 debt that he claims to have lent a friend.
His friend, however, disputes this.
Mr Chew and his wife have two daughters - an undergraduate, 25, who lives on her own, and a clerk, 23, who lives with them.
His wife, he said, is angry with him for lending the friend the money.
Does he feel he was too quick to hand out the dough in general?
Mr Chew rationalised in Mandarin: 'Money comes easy and goes easy.'
Was he reckless, especially in gambling on horses and soccer? He insisted: 'I don't think I spent my money carelessly.
'I spent it on my family, so I don't regret that. I also paid up my flat, so now I wouldn't have to worry about that too. It's money well-spent.'
Now he's hitting the lean streets again.
He takes pains to avoid taking taxis during peak hours and eats at coffee shops instead of at restaurants.
He also has no plans to go on holidays anytime soon because, as he put it, 'money is not enough' now.
Mr Chew said: 'When you have money, spending $1,000 or $2,000 seems like a small matter. Now I have to be more careful when I spend.'
He is still grateful to have experienced the good times even though it was for only a few months.
If lightning strikes again, if he is lucky enough to enjoy another windfall, would he do things differently?
Yes, he would, he said.
But then, he would also entrust a large portion of the winnings from Lady Luck to the other woman in his life - his wife - for safekeeping.
He said: 'I will spend my money more carefully if I win again and I will not trust people so easily again.'
This article was first published in The New Paper on June 22, 2008.