Lester Cherry – Streetwise!

Lester Cherry is a middle aged black man wearing a wide rimmed black hat, recently shined black shoes, blue slacks, and clean white colored shirt.  He spoke clearly and articulately, but with a bit of a drawl, a sort of Southern accent like many Chicagoans whose families migrated from the American south.  He was selling streetwise in Chicago’s loop in the beginning of August, 2019.

Streetwise is a great newspaper, he told me, that helps the homeless work by employing them to sell the paper.  Rather than beg for change, people sell streetwise; it’s a 27 year old organization.  The paper is $2.00, and a dollar and ten cents goes to the vendor for each magazine sold.   Lester wore a laminated badge with his picture; he was a certified vendor.

I bought a copy of the weekly magazine, which emblazoned in a bright yellow sun above the white hands of concert goers read, “Changing the Way We Fest.”  This issue featured an events calendar, a profile of three music-industry non-profits—the Lollapalooza festival was coming up this weekend in the city’s grant park.  Streetwise profiled MusiCares, which provides healthcare, mental health, and financial assistance for the low wage musicians, artists, and concert workers in the industry, Our Music My Body, a non-profit raising awareness to prevent sexual harassment and assault amidst the sex and adrenaline charged climate selling pop songs, sex, drugs, rock & roll, along with each season’s fast fashion, and Rock the Earth, an environmental non-profit.

Another article, copied from a grant to the John D. and Catherine T. MacArthur foundation, profiled the civil rights and black lives matter youth organization, BYP100, founded in 2013 after the killing of Trayvon Martin when youth, along with buses from the west and south side chapters of the NACCP, St. Sabina’s Catholic Church and the Trinity United Church of Christ flooded Federal Plaza, holding hands and singing demanding justice for the youth shot by Fred Zimmerman who stood his ground, a youth wearing a hoodie and holding a snickers bar.  BYP100, along with Black Lives Matter, had packed the Police Oversight Board chaired by now Mayor Lori Lightfoot, calling the committee a toothless sham, and demanding justice for the police officers who killed Rekia Boyd.

The name of Laquan McDonald, the foster child and Chicago Public Schools diverse learner murdered by Chicago Police whose murder, and the video evidence was covered up until after Rahm Emanuel’s re-election when civil rights and Better Government Association lawyer Matt Topic prevailed in a lawsuit to forcing the City to release video evidence, was absent from the two page spread, which interviewed University of Chicago political science and African-American studies professor Cathy Cohen.  BYP100, the article stated, was “building on Chicago’s long, rich, and varied tradition of community organization, stretching from Jane Adams, Saul Alinksy, and the Black Panthers to Barak Obama..”

I began to talk to Lester, amidst the bustle of street traffic on that busy loop corner on Tuesday afternoon.  He was in a job counseling step program that streetwise offered folks to help get a job, and get on your feet.  Streetwise has been around 27 years.  It was 27 years ago, on January 3rd, that Lester became homeless; his house burned down, 21 people burned alive.  He also lost his job that cold winter.  He was a parking attendant.  And Chicago closed the parking lot he worked at to put up the shell and bean, that big shiny metal monument in Millennium Park.  “The parking lot was bulldozed to build the bean, and I lost my job there.”

“They said it cost $450 million to complete.” I mentioned.

“I was staying at the Paxton Hotel, I jumped out of a window from the 2nd floor.  Saved one person, she jumped out of the 3rd floor. Broke an arm and leg, I saved her, dragged her to the perimeter, cut the chain link gate to get her further away from the fire, and smoke. The fire department when they came got her to the hospital.”  The Paxton hotel was at 1432 N LaSalle, near where the Cabrini Green projects used to be.

“That neighborhood’s changed, huh?” I interrupted.

“Shoot, that’s right.  Now it’s upscale baby! ” Lester exclaimed.  “There’s probably a big condo there now.  It was probably a set fire.  They had to get us out first.  We were just an eye sore to the community; prostitution, drugs.  So they thought, we’ll smoke ‘em out like rabbits.  God be my witness 27 years later.  It was 1993.”

“I heard how that happens.  Arson.  Someone burns the place, they get the insurance money, and can sell the land to developers.”  I replied.

“Yeah, it was a set up.”  He paused.  “But I’ve got a job interview!”  Lester exclaimed smiling, giddy.  “It’s insurance sales, on Harlem and Van Buren.  I’ve got a job interview Friday.  I got an outfit together.  I’m going to get my shoes shined, wear a suit.  I have to look my best, it all has to be perfect, because I’m missing teeth.  Let them be the judge.  This man, look, they are going to look at me, like I’m a child of god.  He’s got a good resume, bachelor in business, experience in sales, they’ll have a meeting, talking amongst themselves, starting he’s been in the league.  Well let’s check him out, give him a chance!  If it works, well, great, if not well kick him to the curb.  I got a haircut, my hat, “He raised the brim of his hat to show his clean cut hair, “I won’t be wearing that to the interview.”

“I’ve got my resume, some grey paper, I’ll stop at staples, get a faded color, grey copy.”  Lester continued explaining his vision.  “Make it so professional, that they will have to give me that job.  I’ll put it on colored paper.  If they ask me what I do, I’ll say, well, I sell streetwise.  I’m not ashamed of streetwise; counselors say don’t tell them.  But they’re going to ask what I’ve been doing all these years.  Are you a dope dealer?  You’re probably selling drugs.  No sir I sell Streetwise.  Some of them like Streetwise.  And if they do, whoopy, I’ve got an in.  If not, well, they’ll probably just not even give me a chance.”

“Good luck,” I said, turning to leave.

“Hey you should probably check out the Writers Association.  It’s at 185 N Michigan avenue,” he called out, before returning to the corner. ” Streetwise!  Streetwise!”  The words echoed off the blue glass windows through the busy streets like a summer breeze.

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