To understand where I’m coming from with today’s post you first need to understand why I no longer give change to homeless people…

Back in a previous life a bunch of my friends came to see me perform at The Second City, and on our way to drinks afterwards through the quiet streets of Toronto’s financial district we were suddenly besieged by a rather distraught man in suit and tie, freaking out because he had locked his wallet in his car and had no way of getting home. Now with this being the era preceding the ubiquity of mobile phones it seemed like a plausible enough story, so we all dug deep and between the five or so of us the guy made off with at least twenty bucks.

I say “made off with” because later that same week I witnessed the very same man in the very same suit spinning the very same bullshit tale to passers-by in broad daylight. Instantly realizing that my friends and I had been duped, I ran up to the guy and tore a strip off of him — verbally, of course. And ever since that day I’ve been wary of anyone asking for change.

So…

Earlier today on the way to Yorkdale for cheap T-shirts I stopped off at the St. Clair West subway station to check out a new local fashion phenom — which would have been a total waste of time, if not for the scruffy-looking dude at the top of the escalator asking for money to get on the train.

On my way back into the station I witnessed a kind-hearted soul dump a pile of coins into his outstretched hand, and judging by his repeated thank-yous it seemed to me that the guy had scored enough cash for an adult TTC fare — no small feat these days, I might add! Further evidence that the gentlemen was now subway-bound: he started down the escalator directly behind me, waving thanks again to his benefactor as he stepped onto the moving staircase.

But a funny thing happened when I got to the turnstile… Buddy was no longer behind me! Acting on a hunch, I retraced my steps back to the top of the escalator leading to the north side of St. Clair Avenue, then underground to the other entrance on the south side of the street. And lo and behold, here was the man of the hour, soliciting change for subway with the same sob story. He even had the nerve to ask me for some. Again!

Instead I politely asked him why he wasn’t on the platform, since it seemed to me from his last transaction that he had everything he needed to be there. He held out his hand with a sad menagerie of pennies and nickels, clearly not the booty I had seen bestowed upon him a minute before. Plus, if he didn’t have enough cash for a subway fare, why pick that exact moment to switch locations? Logic would dictate that his first perch was the lucky one, so he should stay there, right?

Of course in the heat of the moment I wasn’t at all clever enough to articulate any of this. Instead I mustered up my best Clint Eastwood voice and told him it would be an unfortunate thing if he was scamming people.

At this moment he easily could’ve taken a swing at me or worse, something I really must remember when I put myself into these situations; instead he says to me: “I bet this makes your day, doesn’t it… Wandering around subway stations, harassing people.”

This would be an example of irony, perhaps?

I offered to pay his full fare, provided that he accompany me through the turnstile. He agreed, and we shared a bit of an awkward walk back to the fare box. And the thank-you I got as we parted ways somehow didn’t seem as heartfelt as the one I’d seem him dole out earlier.

As I got on the subway myself (in the opposite direction, thankfully) I gave a lot of thought to exactly what I had accomplished here. Here’s my best attempt at an explanation:

For me, there’s certainly nothing wrong with charity — and I speak from some experience here. But I have a big, big problem with any unscrupulous soul who flat-out lies to unsuspecting citizens and rewards their charity with robbery. I also think that I’m within my rights to do some occasional fact-checking should a situation arise that deserves it. Just knowing that nosy people like me are out there might give one of these scam-artists pause for thought before putting hat in hand to rip people off.

Or maybe I’m way out of line, sticking my nose into business that’s clearly not mine, or as the saying goes “kicking people when they’re already down”.

What do you think?