His eyes might as well have a vacancy sign hanging outside them. They stare ahead, unblinking even on a hot day when the heat swirls off the nearby bitumen, mixing with the traffic fumes and leaving everyone else squinting and holding their breath. But you know what? Even with those empty eyes, he can always see you coming.
I've seen him often enough, too, to know how he works. He goes after the softer targets; older women fumbling with their change as they leave the 7-Eleven store he always hangs outside, women with children pleading for an ice cream, old men with their pants hitched high, pockets jingling with change and a limp that slows their progress – all of them giving him enough time to move in and ask for money.
Not me, though. I've given him plenty of opportunities over the years. He always sees me coming from half a block away. But as I near he turns away, those vacant eyes looking down, avoiding my glare. I can't help it. I get aggressive around him. He's one of those beggars I can't stand that seem to be filling our streets in increasing numbers. The tactical type. The hunter of easy prey.
In my mind I've often worked out the conversation I'd like to have: "What do you need the money for, mate? What are you really going to spend it on? I already give to you every fortnight. My taxes pay for your welfare cheque. So stop hassling and pressuring every little old lady who doesn't know how to deal with you."
It's not as though I haven't given to beggars. He has a girlfriend of sorts who works the next block, a frumpy, red-faced woman always wearing a stained dress that barely covers her belly, a short blond bob on top of her puffy face that looks like it was styled with a salad bowl. She's far more aggressive than he is, in your face all the time. Thing is, unlike her boyfriend, she's never sly or calculating. It's a business model that works for her.
Further down the street, an old guy with a nicotine beard and piss-stained pants simply squats outside a shopfront, hand extended. All day. With not much return.
So what side do you choose when it comes to that growing horde of beggars who are taking over the streets of Sydney? Do you give to the army of the broken and the busted or not? Do you give to make yourself feel a little better, to ease that gnawing conscience of yours? Or do you keep walking, staring straight ahead, showing them that you, too, can have a pair of vacant eyes.
A big row erupted in England a few months ago when Nottingham council put up signs advising people not to give to beggars because the money would be used for drugs, alcohol or fraud. The posters were quickly ordered to be taken down by the UK's advertising standards bureau because they were likely to cause offence and reinforced "negative stereotypes".
But some charities supported the council's move, saying there were now enough services for homeless people, and those asking for money on streets should be making better use of their services.
Sydney's charities would beg to differ. This city has the biggest homeless population in the country – at the last census almost 20,000 people were without a home. And that was five years ago. The numbers are soaring – check out your local park or train station. And if you were one of the many all those years ago who successfully waged that war against placing our mentally ill in institutions, saying they would be far better off being "integrated into normal society"; (which the bureaucrats believed was shorthand for releasing them on to the streets), then maybe you're not feeling so smug any more.
All I know is that I'm giving less to beggars these days than I used to. Too many of them operate in well-organised rings, franchising out busy street corners, perfecting the wording on their cardboard signs with the panache and style of marketing research executives. Too many have honed their tactics, blunting the empathy levels of a city where kindness is already in short supply. Oh, look. Another large man with a bushy unkempt beard lying prostrate on the pavement, hand extended, small dog sitting loyally by his side ...
And yes, it would be nice if we could solve this problem by increasing the funding of already overworked charities. Or building more affordable housing. But really, that's not going to happen, is it?
What is going to happen is we'll give less. Our hearts will grow more calloused. And begging will become just another business story where the big guys squeeze out the small strugglers.
Garry Linnell is co-presenter of The Breakfast Show on 2UE Talking Lifestyle.