And I couldn’t stop laughing.

Down some water. Laugh. Dip among traffic. Laugh. Cram an energy bar and stop by the tampon boxes, fast food wrappers and museum-pimping statuary that pool along the spot the Roosevelt Road bridge overlooks both river and the vacant Rezkoville and I laugh laugh laugh.

July. Bike ride. Entire length of the city just for funsies and to end the site on a high note. I’ve been posting about it for a week and a half in stories I wrote between August and early October. You’re all caught up.

This is story #1,000. This site will end on Friday. I will miss it greatly. But I’m not ending, nor is Chicago.

I found crime here. I found death and sex and sin and kiddos playing piggy on summer days in the park. I wept and shook here and I laughed and shook here. I got drunk and kissed girls and took boat rides and played croquet. I wore spiked leather bracelets in one life and neckties in another. This town rattled and made me.

North through the skyscrapers, north through the trendy bars, north through gay neighborhoods and wealthy ones and ones where the poverty bleeds and bubbles from the soil itself. North.

The stories, by god the stories. The people I met! The people I didn’t meet! I’ve talked to dancers and magicians, politicians and thugs and drunks. I hit this city with all I had and at the end I told so, so few of its tales. This city threw itself at me and I gave it a pittance, my thousand stories trickle and tinkle against the ocean this Chicago throws back each moment.

In June 1921, Chicago Daily News reporter Ben Hecht debuted “1001 Afternoons in Chicago,” a daily column slicing life in the first quarter of the 20th century. In the preface to the book version, editor Henry Justin Smith recalled the “haggard but very happy” Hecht turning in the first few columns.

“It was clear that he had sat up nights with those stories. He thumbed them over as though he hated to let them go. They were the first fruits of his Big Idea — the idea that just under the edge of the news as commonly understood, the news often flatly and unimaginatively told, lay life; that in this urban life there dwelt the stuff of literature, not hidden in remote places, either, but walking the downtown streets, peering from the windows of sky scrapers, sunning itself in parks and boulevards. He was going to be its interpreter. His was to be the lens throwing city life into new colors, his the microscope revealing its contortions in life and death. It was no newspaper dream at all, in fact. It was an artist’s dream. And it had begun to come true. Here were the stories. … Hoped I’d like ‘em.”

By 1925, Hecht was sick of it. He had written a deliberately smutty novel called “Fantazius Mallare” as a test case on American obscenity law, and American obscenity law won.

He was fired from the Daily News in 1923 but had with a group of friends from the Dil Pickle Club arthouse scene started the Chicago Literary Times, an inspiring, brilliant drain on time and funding. Writer pals were calling about easy money and literary fortune in New York, and Hecht was ready to submit.

These are the final lines of the last 1001 Afternoons in Chicago story, “My Last Park Bench,” in which an older, weary Hecht stumbles across the younger version of himself.

“I catch a glimpse of him following me with his eyes, excited, damn him, over the mystery and romance which lurk in every corner of the city, even on a cinder-covered bench in Grant Park. Let him sit till doom’s day on this bench; he will never see me again. I have more important things to do than to collect cinders under my collar.”

I didn’t know when I started that Hecht was a liar and fabricator, a newsman conman of the era for whom Truth and Fact formed a Venn diagram, and none of it mattered so long as the words sang. He ended up in Hollywood, his gift for witty lies finding a more appropriate setting than a newspaper page.

I just knew I wanted to try what he claimed he was doing.

Since April 2012, I never missed a scheduled post day and, aside from some clearly satirical stories about mascots, Santa Claus and the brainstorming session for “tronc,” I never made up a word. What you read from me over these last six years is Chicago in the 20-tens as seen through my lens and microscope.

Hope you liked ‘em.

I was laughing when I hit the graveyard.

I made it. I made it through my self-assigned task. I made it through Chicago and I made it through, Chicago. My throat was dry and my legs burned white like charcoal ready for meat. But I was laughing.

My side trips and roundabouts added almost 20 miles to the route. Had I stuck to the path, I could have gotten there at 30. Instead the app tolds me I took 49.86 miles to get from Burnham to Evanston, plowing through that town between.

I’m not done yet. Not with my 1,001 stories, not with my half-century ride. Just a touch more to go.

I turned the bike around and headed back into the city, aiming my aching bones, burning legs and slightly chafed uppity bits toward the Howard Red Line stop. Nothing left in me, I slouched toward Bethlehem to be born.

A CTA worker came out of her glass cage to greet me.

“No bikes on the train,” she said.

And I laughed.

…

Read a few of my favorites:

The Rabbi’s Machine is Missing — Whatever happened to Chicago’s last typewriter repairman?

The Human Addict — A begging addict talks about being treated like a person.

Old Joe of Canaryville — Joe sits in his shop waiting for customers, as he’s done for 68 years.

Nuns in a Cash Register Store — Another bit of Chicago is lost.

The Nut Hut — Over soup, a woman recalls her role as a professional tease in a prostitution scam.

Party at Uncle Fun — Customers, staff and Uncle Fun himself say goodbye to the well-loved Belmont gag shop.

The Murderess Down the Block — I find out a 1920s lady gunner lived a few houses over from me.

The Most Sarcastic Child in Chicago Watches a Clown Show — Clowns from Theater Oobleck and El Circo Nacional de Puerto Rico win over a very sarcastic child.

The Steelworker’s Mermaid — How four sculptors hid a seven-foot mermaid for 14 years.

Mama Olaf — An immigrant tale of love and tripe soup.

Miss Sweetfeet Breaks — A breakdancer talks about the need for more B-Girls.

Light and the Rocket — A child I knew just killed a man.

The 16th Artist — One man’s arts center aims to revive Englewood.

The Rabbi, Harry Potter and Too Many Corpses — A rabbi has to tell a little boy some bad news.

Whatever Happened to the High Priestess of the Flappers? — In 2016, I wrote about the head of a 1920s clique of teen glamour girls. In 2018, her granddaughter reached out.

The valley is a small recess in the pavement, a tree-ringed micropark marked with stone tables and stone chairs inlaid with chessboards. They’re meant for passersby, to aggregate a collection of charming old men who toddle to the neighborhood park to stretch minds and capture bishops. A statue of two children play in and are a water-spraying fountain among the black-and-white battlefields.

But there were no chessmen. Just a ton of dogs.

Big dogs, little dogs. Dogs on leash and a pair of doggie pals wandering leashless circling the fountain. Kids ran and scampered and neighbors chattered as, near to a one, every chess table was topped with dog.

I asked a man holding the leash of a large brown fluffball standing on queen’s rook 8 if this was a dog park or not. He pretended not to hear me, but a woman holding the leash of the dog one board over responded.

“Yes,” she called to me.

Cover blown, the man smirked sheepishly and responded to my initial question.

“Well, not sanctioned, but we do,” the man said as his companion, unnerved by the sudden pause in petting, attempted a Falkbeer Countergambit right on the table.

I left charmed by the odd little enclave of tables with dogs standing on them. Kids — both statue and otherwise — played in the fountain. Friendships were made among dog and man. Handshakes were extended. Butts were sniffed.

And the chess tables intended to bring together a community did, just with fewer rooks than intended.

Read about a chess space used for chess

Read about a woman who tours Chess Records

Read about an imprisoned politician who owned “Chess” by Murray Head

The distance and the scream of cars rushing over the avenue make it an oddly silent game, little marionettes stepping forward to underhand bean bags into the sky, hoping their loft comes ka-thunking down near the board set up on the game’s other side. One man makes an odd wooting call that cuts through the traffic for a moment. Wha-ooo, not wha-hoo. Wha-ooo.

You’re standing by an empty lot that used to house a corrupt alderman’s bar.

…

A friend had included me on a group email a few weeks back, looking for the exact location of Paddy Bauler’s old saloon. This was where the Old Town alderman from the ’30s to the ’60s took bribes, made connections, held court before his crowd and once shot two police officers who called him a fat Dutch pig.

The officers survived and Paddy was let go — that’s the kind of pull he had.

I didn’t/don’t know much of anything about Ald. Bauler, but did enough online digging to proudly and confidently declare the exact wrong location to the group. But an old photo I found, coupled with Google Street View, helped my friend discover the actual location.

It’s an empty gravel lot next to a “European Wax Center” on North and Sedgwick. The waxing salon is a fun find to describe — photos of smiling and presumably hairless blonde models in the window and “Walk In, Strut Out” static-stickered on the door — but the lot that actually held Bauler’s liquor-laden HQ was just a lot. Gravel. Security lights. A threatening Lincoln Towing sign below a Corona billboard. And commuters streaming by every few minutes as the Brown Line deposited them home, oblivious as to why a man is leaning on a metal fence to stare at a gravel lot.

They say those who don’t learn from history or study history are condemned or damned or doomed to repeat it — the idiom has multiple forms, all of which are nonsense.

It’s one of those emergent expressions that doesn’t mean a damn thing what it originally did. Exceptions don’t prove rules, raising a question isn’t begging it and “Those who cannot remember the past are condemned to repeat it” was originally describing early childhood mental development, complete with a 1905 slam against “savages” and “barbarians.”

In its modern interpretation — that not studying Nazis is how you get Nazis — is equally wrong. We study Nazis all the time, yet currently seem to be infested with them. There must be a nest under the floorboards.

But it’s not just that the phrase isn’t true. It’s that the opposite is what’s true.

People who don’t know history live in a perpetual now. They walk by and see an empty lot of rocks, gravel and some potential parking for when they get their bikini lines done the European Wax way.

People who learn from history are the ones destined to repeat it. They’re condemned to repeat it over and over every day, to know just enough about the world to be distracting and to see the ghosts of bars and streetcars where others see rocks and parking.

God bless.

God damn.

I spent way too long trying to find out the exact location of the Second Precinct of the 18th Ward in the 1884 presidential election, working myself into a lather of old maps from names like Mitchell, Cram, O.W. Gray & Son and something called “Rand McNally” before realizing it didn’t matter.

On Nov. 18, 1884, somewhere south of Division, west of Franklin and east of the river, election canvassers opened an envelope containing the returns from the recent state senatorial race in the Sixth District and found the lousiest election fraud in American history.

“The word ‘four’ in the sentence ‘Henry W. Leman had four hundred and twenty votes for State Senator,’ as it was originally written, had been erased, and the word ‘two’ had been written in its place. And the word ‘two’ opposite the name of Rudolph Brand, as originally written, had been erased, and the word ‘four’ written in its place, making the vote to appear to be four hundred and seventy-four instead of two hundred and seventy-four,” a later history of Chicago would recall.

The Chicago Tribune from the next day concurred with the memory, adding the even sadder detail that the new numbers were written “in a peculiar shade of ink differently colored from the rest of the writing.”

Maybe today it’s in the offices and yupscale bars of River North, or in that big community garden along Chicago Ave. Maybe it’s where the condos bloom by the former Cabrini-Green or in the last industrial holdouts on the southern half of Goose Island — it doesn’t matter. Wherever it was, someone committed a fraud parents would laugh at a grade schooler for pulling on a report card. They scribbled a two to a four and a four to a two in the wrong color.

If you know anything about American politics in 1884, you’re probably congratulating yourself for remembering Grover Cleveland had two non-consecutive terms. But elections were nasty affairs at the time.

A far cry from today’s grade-school gyms manned by sticker-dealing old ladies, elections were semi-secret, sometimes violent affairs held at saloons and other spots voters could be easily spotted and bullied into submission by poll-watchers and marshalls the parties picked for intimidation factor.

Down at State and Harrison the same election two became four, the race turned bloody after two poll watchers — one with the awesomely 1884 name of Black Jack Yattaw — drew guns after each tried to arrest the other for trying to sneak in the room where the ballots were kept. En route to the jail with a mob cheering murder, those guns went off and an election constable named Curran ended up dead.

“He may be a very bad man but he was not on trial for that,” his lawyer told the press after Black Jack was cleared of the killing.

Back in the 18th Ward, the sketchy con of two and four got sketchier. The Daily News found out that a few days after the two and four were spotted, the ballot box was taken to a saloon nearby the old courthouse at Dearborn and Hubbard to be stuffed with hastily added ballots to confirm the hastily scribbled numbers. They were all new and clean, recently printed and folded in the exact same manner.

The forgers even put down Leman’s father-in-law and brother-in-law as having voted for Brand.

The race was vital in setting the razor-thin party majority down in Springfield, and the precinct was vital in the race since, overall, Brand had “won” by 10 votes. The legislature and the governor later flopped the results, giving Leman his likely rightful seat. The printer who forged the hasty ballots flipped on the conspirators, there was a trial, jail, fines and a later pardon.

“He is not as pretty as he once was, but he knows a heap more,” the Trib wrote of one pardonee.

And that is the sum of American political history. All it’s ever been, from bloodshed by Black Jack to the modern fiddling and finagling with district boundaries, is a battle to switch two to four and four to two.

They used to scribble twos into fours and get all Black Jack gunplay if someone deigned to stop them. Nooses were brandished and often used against black voters to make sure those fours never got to a polling place. Political hacks would slip beers and bribes to rum bums to add to columns early and often, just so the lesser candidate would get the nod, four and office.

Then we grew up and got all fancy about it. We screamed over hanging chads and electronic voting machines that maybe are hackable I’m not sure. We learned to rig the game on a macro level so we didn’t even have to bother with stuffing ballots. We even learned to use fraud to create fraud, harnessing the specter of the bad old days to invalidate reforms that would allow millions more low- and moderate-income citizens of color to access democracy.

A president who lost his way into office now screams three million to five million of the votes he didn’t get were super phonyfake. Some believe him. Some will just capitalize on his jeers to force-feed the nation new voter ID laws, tighter restrictions on polling tech, locations and hours, other new methods of disenfranchising voters and turning that four into a two that I’m neither clever nor evil enough to concoct.

At its core, all this statistical, technological and legislative hugger-mugger amounts to fancy modern ways to swap a two and a four to get the race to come out how you like.

You have to use the past imperfect a lot when writing about history, because it was. They used to do this. They used to do that. But don’t think the game has changed that much, that we’ve somehow gotten more clever or noble.

They’re still swapping twos and fours, and we’re still here, watching, waiting and fighting tooth and nail to stop them.

Read about more bloody 1800s politics (including Black Jack)

In the wake of Trump, can a good person support the Chicago Cubs?

Cubs/Trump, part two

It’s the type that starts in a comedy club with a curtain over the door so the comic doesn’t get a blast of light in the face every time someone has to go to the bathroom.

It’s the type of story that starts with wait staff filing and shuffling people into seats, taking drink orders, bringing up napkins and plates of fries for table to split, gliding around with pitchers and smiles as others file more hungry, thirsty faces in.

It’s the type of story where a man you’ve only seen on TV comes up wearing cloth reindeer antlers, casually shakes your hand and says, “Hi, I’m Greg” before moving on to do the same at the next table.

But none of this is the part that makes you sound old. That comes when you say something silly like “Huh. A live podcast.”

Old man.

Podcasts, for that small subset of people who read a tri-weekly lit blog but might not know much about iTunes (Hi, Mom!), are downloadable radio shows people make available for free online. From guys goofing with a recorder in basements to national obsessions like Serial, podcasts are radio without the economic pressures that turned a vibrant medium into wacky morning zoo crew DJs hitting play on pre-approved autotuned pop hits.

Explaining podcasts like they’re something no one has heard of also makes you feel old.

The Greg who shook your hand is older than you are. It’s Greg Proops, 55, former star of both the American and British versions of 1990s improv comedy show “Whose Line Is It Anyway?” He’s a mid-career standup, versed in a style of comedy that peaked with the third most-popular TV show Drew Carey ever fronted.

The room filled. Proops wandered the club, chatting with and getting gifts from the fans who packed the place for the live taping of “The Smartest Man in the World,” the podcast.

Drinks came. Plates clattered. The lights dimmed.

Music played and Proops came on stage, dancing to the crowd’s deafening cheer. The show, this show by a man you had only seen riffing on suggestions shouted by pastel-clad 1990s audiences, was astounding.

Sitting behind a tiny, black-draped desk in the middle of a wide, empty stage and never taking off the reindeer antlers, Proops stunned. He improvised lovingly for an hour on the audience gifts, then thundered on Ferguson and the CIA torture reports. He quoted the sacred texts of a half-dozen religions in the same two-hour set where he made a little cardboard cutout of a kitten talk — and it worked.

More personal than a stand-up set, more timely than spoken word, less FCC-ed than radio, this was Mort Sahl at the hungry i. This was an improvised Spalding Gray.

This was one of a rising tide of performers cut loose from 22-minute formats and sponsor-approved wackiness. This was a performer freed.

Most of the people who will laugh at that weren’t in the club with the clinking glasses and curtained door. They’re on trains or listening to car radios. They’re sitting at work with earbuds in or walking down the street trying not to be harassed.

That moment of freedom in a Chicago comedy club lives online now. And, barring magnets in a server room or the entire planet giving up the Internet as a fad, that moment will live forever.

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Download Proops’ podcast

Two new appearances coming up in January

It was wrapped around, as lines should be. The perfect length to show that, yes, what’s happening in this small storefront in Old Town is worth seeing, worth waiting for, worth wrapping around a building for.

“I don’t know how clear your conscience needs to be, but the line starts back there,” a man in line snipped as I walked in the doors.

I shot him a look somewhere between obsequious smile and a 14-year-old girl’s interpretation of withering.

“We’re heading up to will-call on the second floor,” I said. “My conscience is fine.”

Over the previous 24 hours, I had eaten deep dish pizza, gone to the Bean and Marshall Fields, brunched, dined, talked about buildings, made plans then broke plans to go up the Sears, walked Michigan Avenue and done all the other things you do when family is in town.

And now Second City.

The Second City theater in Old Town is:

• the global hub of a comedy empire with offshoots in other cities, through touring companies, on cruise ships and at any other place aspiring improv comedians flock for the sheer love of asking audience members to name a profession, a celebrity and maybe a type of plant.
• the training ground for pretty much everyone who has made you laugh in the last six decades, from Nichols and May to Keegan-Michael Key.
• a machine that produces comedy, one clockwork in its precision.

Before you’re even inside the doors, the signage reminds you how much you owe them. John Candy, Gilda Radner, Bill Murray, Stephen Colbert, Tina Fey, pre-nosedive Mike Myers — every square inch is plastered with the faces you know and love.

The nostalgia buttons pressed, the logistics come into play.

There’s a man with an earpiece answering questions outside, a coat check guy waiting inside, will-call, check-in times, a line that happened to meander by the souvenirs and a staff with the sureness of a collegiate marching band on the field spreading to exact spots to answer questions, direct traffic, intercept strays and guide them back on the path to the room where the funny ha ha was about to go.

Then, the room, where smiling people in black T-shirts played human Tetris, shifting and shuffling the milling herd into crisp perfection. It was row after row, tile after tile of fan lodged in a room snug up against each other, all with a view of the stage and a table for drinks.

Then you’re told you’re going to see some wacky.

As for the act, it was good. Funny. Two hours of sketch followed by some improv I ducked out on because 1 a.m. passes my threshold for watching people make stuff up.

They did funny accents, they really sold their characters and they threw in a few topical references, just like SNL, SCTV and any other place where Second City alumni did funny accents, sold their characters and threw in topical references.

It followed all the rules for looking like it was breaking the rules.

I don’t know why I’m being so harsh to people who just wanted to make me laugh. The cowboy sketch was brilliant and the coma sketch touching and deft. Every performer was on. If I had seen this same show with the same actors in a dingy little theater, I would never stop telling people how brilliant it was.

There’s a Second City way of doing comedy. The wackiness has become codified and being marched past six decades of photos of identical reaction shots and wacky mime scenes didn’t make me excited for what I was about to see. It made me excited for Bill Murray’s past or these actors’ future.

The biggest laugh of the night came for me when my family and I tried to cram in for a selfie. Since we were all Tetris-wedged, it was hard to get the five of us in one shot. One cut off everything of my uncle but his hair. Another squooshed my cousin and his girlfriend together in a sort of weird way.

And I laughed and laughed and laughed.

It was a small moment — all my favorites are — but it was real. For me and probably no one else, that’s the moment I would have waited in line for.

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Read about a show I loved a whole lot more

Just down the street from a storefront just marked “BEER,” no one was interested in the best margaritas in Wrigleyville.

The windows and doors had been thrown open to let the spring warm patrons who would hopefully come in to watch the Cubs lose badly on the many, many TVs stationed around the bar.

It wasn’t working. I was alone with my Victoria.

The bartender, a short, muscular Hispanic man with a military cut and a tight black T-shirt, was telling me how no one was cheering the game. I was listening because when I asked for “A bag of chips or something,” he went over to the restaurant section and brought me warmed tortillas with a red salsa I just wanted to drink.

“Sometimes you can hear people cheering on TV and cheering from outside,” he said, gesturing at the screen.

Some radio announcers gave a lackluster “Take Me Out to the Ballgame.”

“Not this game,” the bartender said.

People would wander by, occasionally peek through the opened windows to check the score. Men and women in Cubbie blue, mostly. The women were blonde, mostly. The men were tall, mostly.

I did recognize one of the wanderers. He was a short, dreadlocked man who had tried to bum money off me when I was walking under the ‘L’ tracks before finding the bar. I disliked him because he called me “Boss-Man,” which I’m pretty sure was an attempt to play off white guilt.

He also asked for “a couple of bucks” instead of change and he wore a blue button-up shirt with a white collar like an investment banker in a movie.

I just don’t give money to anyone dressed nicer than me.

The bartender started a story as the man walked off.

“This guy came by, he was talking to these women through the windows. He started to bother the customers,” the bartender said.

“I mean, they were beautiful. I would like to have a conversation with them. But when you’re bothering the customers, it’s a whole ‘nother thing. I go out there and tell him to get out of there. But he won’t go. And then he shoves me.”

The bartender glared out the open window, then turned back to me.

“So I punched him.”

2. Old Town

He had a red and black doo-rag split down the middle like Harley Quinn. He had an all-black track suit. He smoked the roach of a cigarette in thick, flamboyant drags.

He asked me for money.

I checked my pockets.

“I’m just checking,” I cautioned.

On a warm spring night by one of the seedier gates of Old Town, where the crowds off the Red Line Clark/Jackson stop have to make their way through a tunnel of drug deals to get past the Division construction. Past this streak of all-night fast food, cell phone stores and questionable financial service storefronts of neon, there’s LaSalle traffic, Planned Parenthood and a walk through an instantly gentrified slip of bars before getting to the bus stop where a man with bright colors split like a comic book character asks for money.

I checked my pockets. The man was nice. I forget what he said, but I liked his patter. Something about it seemed more pleasant than the usual panhandle sell.

I didn’t have change, so I offered a dollar. It was dark and no bus had come past in quite a while. I took the bill and reached over to him, it nearly brushing his fingers.

At the last moment, he held a hand up and refused the money.

“Can you buy me something to eat instead?” he said.

3. Noble Square

The man in plaid took the plastic bottle he had been drinking from and whipped it across Milwaukee like he was skipping a stone. He watched it skid across the road, listened to the long, strict scraaaaaape as it skidded skidded skidded and finally hit the curb on the other side with a small clear bounce.

He made a “nailed it” gesture with his fist and continued his stumble down the road.

He wore plaid. He wore many plaids. He had cut the sleeves off the large, tan flannel so you could see the snugger red flannel sleeves underneath. His baseball cap and the shorts that stopped above his knees were bright red, but extending from under them were tan flannel pajama pants pulled tight by the socks and shoes they were tucked into.

He was drunk and homeless, stumbling past the stores and bars of the stretch of Milwaukee between Ashland and the highway.

A group of buxom 20-somethings with Lennon glasses and peace sign necklaces filed out of a restaurant and headed single file down the sidewalk, cutting ahead of me.

In a row we walked, the patchwork man of many plaids, four slutty hippies and me. We neared the packed outdoor patio of the bar where ’60s night raged.

1. Wrigleyville

“He shoved me first, right? And these two officers, they were walking across the street. They were getting pizza and they see that. So they come running over and I’m like, ‘Officers, he touched me first.’ And they’re like, ‘We know. We saw. We were just coming over to help.’”

The bartender chuckled.

“He went down like ‘Aah!’” he said, miming a man putting his hands straight up and falling backward.

The bartender rolled his eyes as he “fell.”

“The cops are like, ‘What do you want to do with him?’ And I don’t want to press charges, I don’t want nothing to happen to him. I just want him out of here. So they took him a few blocks away and let him go.

“And now the guy keeps coming back around,” he said, nodding at the window.

I looked out the open windows onto the Cub-garbed drunks and flashing lights of Clark Street.

“What guy?” I asked.

“The black guy!” he said.

“The guy with the shirt?” I asked, quickly tugging my own collar for emphasis.

The bartender nodded.

“He asked me for a couple of bucks,” I said.

The bartender shrugged.

“I just don’t give money to anyone dressed nicer than me,” I said, shaking my head and taking another warmed chip.

2. Old Town

“Look, I’m just going to get one of these cabs and go,” I said. “Just take the dollar.”

“We can just go down there and get me something. I’m hungry. I’ll wait outside.”

“I’m just going to get one of these cabs and go,” I said as two cabs that had been waiting at a light passed by me.

“We can just go down there, you get me something to eat. I’m hungry.”

“Just take the money,” I said.

He stopped and looked down at the bill I was holding out to him.

“If I do, can I have a couple more. I’m hungry”

“Sure,” I said, opening my wallet. “I’ve got to get one of these cabs though.”

I was now holding two dollars to the man. He looked at them, then back up at me.

“If we could just go down there and get-”

“It’s not the money — it’s the time,” I said. “I’ve got to get one of these cabs and go home.”

“I’m hungry,” he said. “I know you don’t believe me-”

“No, I believe you,” I cut in, annoyed as I eyed another cab go by. “I wouldn’t have given you $2 if I didn’t believe you.”

He stopped and looked at me. I looked back at him. Emboldened a little (and maybe that white guilt from earlier), I repeated, adding a bit.

“I believe you,” I said. “You asked me to buy you food.”

He stood a little sideways, at that standoff angle people do when eyeing someone suspicious.

“Thank you,” he said, taking the money, then holding out his hand for me to shake.

3. Noble Square

Nothing happened. The man in plaid stumbled by the den of sprawling young drunks in ’60s gear. We lost the girls to the bar. I realized I was catching up to the man, so I slowed down, eventually turning down a street I didn’t want to just so I didn’t get near him. He scared me a bit.

I left the man in plaid stumbling under the hazy amber of a streetlight as he headed toward a highway he would never take.

Something true just happened on Chicago’s North Side.

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Now read something true from the South Side

Since I don’t give Stanford-Binets to every panhandler who’s crossed my path in the City That Mostly Works, I just think he was the smartest bum I ever met, just like I think it was in Old Town, I think it was 2009 and I think it was one of those clear, hot summer days with that tang of humidity that just makes everything irresistible.

And by “bum,” I don’t mean “homeless person.” This guy was a bum. You’ll soon see.

I was on a sweat-laden bike ride when I saw a store and decided I needed peanuts.

Outside the store was the world’s cleverest hobo. I didn’t know it at the time, but there he was: not smiling, not talking, just looking forward and holding up a StreetWise. I was in a good mood, so I said I would get him on the way out. He didn’t say a word, just sort of grumbleshrug looked away. That’s the important bit.

The store was an organic, healthy, artsy-fartsy sort of place, so I ended up spending too much time looking at cruelty-free wines and cheeses I probably shouldn’t be buying. So I bought my peanuts and clutched two one-dollar bills from the change to purchase the rarest commodity of all — liberal righteousness.

I did not plan to buy the StreetWise (which, for the uninitiated, is a Chicago magazine/social service group notable for giving homeless people gainful work as magazine street vendors). I, like most people who “buy” StreetWise, planned to give the vendor my money and then say in a loud voice, “No, keep the magazine.” Then I get thanks from the vendor for allowing him to sell the magazine at least twice (probably more — lots of liberals on the North Side).

I handed the man the $2 and waited to decline his offer.

Then, nothing. He just took my money, put it in his pocket and looked away.

I looked at him. I looked at the pocket holding my $2. I looked at the StreetWise he was holding out. And then I looked at his neck, which was notably absent of the ID lanyard all official StreetWise vendors wear. The dude was just a bum with a StreetWise.

I was peeved. I was pissed. The two bucks was nothing — I should report this jackass for taking advantage of a good organization helping people in his situation.

Then it hit me.

Remember how I said him not saying a word was the important bit? He had never claimed to be a licensed StreetWise vendor. He never claimed to be anything other than a guy who holds magazines weird. I couldn’t do a damn thing.

“No, officer. I was just sitting here sunning my magazine when this guy hands me two dollars and just stares at me. He said he wants my magazine? Wait, he wants me to offer him my magazine so he can tell me to keep my magazine? And then he called the cops to report me for holding my magazine misleadingly? Yes, officer, I will press charges. Can’t be too safe — lots of weirdos in this town.”

I moved on, leaving my money with the cleverest hobo. He sort of earned it.

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