I’m meandering down a rural road on the Caribbean island of Grenada, and a Black man on crutches is slowly heading toward me. He’s thin, rheumy and raggedy, like the increasing numbers of homeless people in Chicago.

I decide to do what I do back home: make minimal eye contact so I don’t seem like a jerk and slip past before he can ask for money. It’s Grenada, a poor country, so I’ll give him something when he asks, though I wish one of us were invisible.

Maimonides wrote that the second highest level of generosity is to give anonymously, without seeing the effects of your giving. His highest level is to anonymously give before someone needs it, before they have to ask for it. With the homeless when I give at all, I’m usually at Maimonides’s lowest level--giving, when asked, while feeling guilty, resentful or condescending.

When we’re within yards of each other, he smiles broadly, so now I can’t just slip past him with a quick eye contact. Then he holds his hand up in a friendly hi, compelling me to do the same. I’m trapped.

“Good morning!” he says.

I tell him hi, thinking here comes the gimme.

Then he sticks out his hand, so I have to shake, the physical contact setting me up for the money touch.

“My name’s Tony,” he says.

“I’m Garry.”

“Glad to meet you,” he says, “Beautiful morning beautiful morning.”

He swings past me on his crutches, leaving me feeling bad about myself.


— Garry Cooper, MSW

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