The Homeless Philosopher

DALEY PLAZA, CHICAGO — I pulled out my wallet to give money to the homeless guy who accosted us the other day while we were in the southeast corner of the plaza. He approached us quickly and began babbling about needing train fare to visit some family for the upcoming Thanksgiving holiday.

I was intrigued. I wanted to hear his story; as a newspaper guy, I spend most of my days asking questions of people, gleaning tidbits of information and observations from them to compile stories. This was an opportunity to get a behind-the-scenes look at the man's plight and how he got into his situation; a front row seat to one of society's issues.

So I took out the wallet.

And that was a really stupid move akin to opening a can of tuna fish in a cat shelter, or throwing one chunk of steak into the lion's den, or telling a horde of Black Friday shoppers that whoever can get to the huge flat screen television first can buy it at 80 percent off cost.

I had returned to the area last week to visit the Illinois girl who has changed my world. We decided to take the Metra commuter train into the city and spend the day walking around the Loop. She, since having lived there for years, acted the normal urban person. Me, on the other hand, gawked and pointed at buildings and came across like some southern hayseed. A rube ripe for the takings.

We had difficulty finding the Plaza. A street map app on my phone kept misleading us in different directions and by the time we ended up there, we were a bit worn out. Also, we couldn't actually get into the plaza because vendors were setting up for a large event there and instead, we had to sit on the perimeter. And that's where the man found us.

I handed the guy $10. But that wasn't enough. The train ticket, he said, cost something like $14.95. My Illinois girl gave him $1, thinking it was a $10 bill, in an effort to get rid of him. He became adamant, wanting more money. She gave him a $10 of her own.

“I don't have any family,” he said, welling up fake tears and beginning to whine. He needed the money. Needed it desperately. I didn't think at the time to question his contradiction. No family? Just moments ago he said he needed a ticket to visit family.

Instead, I reasoned with him. “I don't have any family, either,” I said.

“You got a wife,” he pointed.

“Not yet,” I countered.

“Well, you got love,” he replied.

And, by gosh, blurting out of the mouth of an obvious guy with some mental issues came forth an observation I couldn't contest. I paused, almost stunned by the beauty of it.

But then he snapped me back into reality. He offered to trade places with me and made an exaggerated high-stepping motion, like he was becoming me, taking over my role. In my mind I wanted to tell him to be careful what he wished for. He wanted to be me? With a career in newspaper — one of the worst financial forms of employment — and a home mortgage with Wells Fargo? I was tempted to make the switch with him merely for economic reasons.

But then it got weird.

He made kissing faces and said he would marry my Illinois girl. He stepped toward her, but never got too close and I got between them, acting as buffer for her safety and to deflect any marriage proposals. I mean, I've known her for only a few months and never got that aggressive. If this homeless guy who probably lives in an Amana refrigerator box somewhere by the Chicago River could sweep her off her feet and away from me, I may have to change my strategies.

We left quickly; he remained in the Plaza, talking about having love and all.

The Chicago Coalition of the Homeless estimates there are close to 90,000 people living in the streets of Chicago. It's hard to get an accurate count because of the transient nature of the homeless. But of those 90,000 or so, we came across the philosopher who espouses love, all the while pleading for cash.

So, was it worth it? Maybe. We saw something different, got an insight into homelessness and received a memory. Although I kicked myself for putting my Illinois girl into any harm's way by being stupid and country.

Later, as we sat in the Ogilvie Transportation Center and waited for our train out, a young guy approached us and asked for $10 to “stay in a hostel.” I started to say something, but my Illinois girl, who opted to stay with me rather than fall for the Plaza guy's advances, quickly took over and told him we had already been hit up on by another guy and we didn't have the cash.

This time, I knew to keep my mouth shut and forego getting any story.