For many years, I worked in the River North area.  I’d take the train in, then walk about 20 minutes to work.  Along the way, I heard every street sob story you can think of.  Nice-shirt-and-tie white guys are juicy targets.

Here’s how I viewed it:  if you’re out on the streets of Chicago bothering people for money, you must really need money.  I understand, times are tough.

But, like everybody who passes you by, I also want you to work for your money.  So here are my simple rules:

Don’t stop me.  If I’m walking, I need to get somewhere.  If you want to do an Aaron Sorkin walk-and-talk, that’s fine.  I mean, you’re probably going to do it anyway.

BE ORIGINAL.  If you at least put some effort into it, and have a sunny disposition, and can ad-lib pretty well, and amuse me at least somewhat, I’ll give you a buck.

If you haven’t memorized your material and have no confidence whatsoever, scram.  No soup for you.  Clean your desk out immediately.

Appearances don’t matter to me, but if you reek to high heaven, just move along quickly.

P.S. I have a finite amount of cigarettes.  They’re expensive.  I think giving 70% of my pack to you people is quite generous.  And quit trying to pocket my lighter.



One of the more popular scams was the “out-of-gas” bit.  A guy would stand there with a gas can, then say something about needing money for gas, his car’s down the road, his wife’s in labor, he’s trying desperately to stop an assassination attempt, etc.

One day I saw one of those guys.  I had to take action.  He started his rap and I said, “look, man, if you’re going to scam people, at least be original.  I’ve seen this about a dozen times.”  Then I walked away happy, knowing I’d given sound business advice to an upstart American entrepreneur.



On my last visit to the city not long ago, I met up with family members for drinks on a weeknight.  Many hours later, about midnight, I was walking down Wacker Drive from the subway to the train station.  Then a very lively old dude approached and chatted me up.  There was no one else on the streets.

He was a hoot.  For about five blocks – and we were walking at a slow inebriated pace — he was going on about his ex-wives.  And, of course, he needed money, but the guy had some material.  I was playing the straight man.  He loved it.  We were like Redd Foxx and Dean Martin (I was Dean Martin).  We both laughed a lot.


I ended up giving him my wallet.  I was really drunk that night.