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These Vigilante Night Watchmen Are On The Prowl in Bridgeport

By Ed Komenda | November 23, 2015 6:52am | Updated on November 23, 2015 11:20am

BRIDGEPORT — On a recent Friday at 8:30 p.m., a black SUV rolls to the stoplight at 31st and Morgan.

Inside sit three men, neighborhood guys who live on the same block east of Halsted: Preston Breunig, Tom Bailey and John Jaramillo.

Armed with nothing more than cell phones, a police scanner, clipboard and coffee, they are here to keep the neighborhood safe.

Meet Bridgeport’s night watchmen.

Their mission is to rove the neighborhood, looking for everything from burnt-out streetlights to trouble buildings to gangbangers hanging out, dealing drugs and flashing signs in Bridgeport's darkest corners.

These unarmed men carry another name in these parts — one you might be familiar with: Neighborhood Watch.

“We’ve got contacts in every part of the neighborhood,” said Bailey, a 59-year-old help desk technician for the City of Chicago, sitting in the SUV’s passenger seat. “We do all of Bridgeport.”

It’s a campaign Chicago Police want in the neighborhood — as long as watchmen stay out of harm’s way.

“We don’t condone where they’re actually getting themselves involved in the problem: If gangbangers are around the corner, we don’t want them jumping out of the car and grabbing a gangbanger,” said Chicago Police Sgt. Martin Loughney, a CAPS officer in the city’s Deering District. “You’re just watching. ... You see something and you call police.”

In 2008, the U.S. Justice Department released a study that found citizen policing programs like neighborhood watch contributed to a significant reduction in crime: a 16 percent decrease in communities where residents took to the streets.

Bailey heads up the watch and drives through the neighborhood with a revolving cast of Bridgeport residents about four nights a week for two hours at a time. He fills out a log book with dates, times and sightings to share with police and city officials.

You’ll find him at every CAPS meeting for Beats 913 and 915, updating the public on what’s happening on the streets.

A towering man in glasses, Bailey has a mathematical brain capable of conjuring up addresses tied to crimes and shady landlords. If there’s a police report somewhere in the world sporting a Bridgeport address, Bailey probably knows about it.

And he's keeping a close watch.


“Look at the boys coming through the alley,” Bailey says.

The SUV is rolling down Poplar Avenue, near 30th Street, when the watchmen spot a group of teenagers hanging out under the yellowed streetlights with their hoods pulled up.

“That’s the SDs," Bailey says.

He’s talking about Satan’s Disciples — one of the two street gangs that roam the neighborhood selling dope. The boys are lumbering some place fast.

According to Breunig, a stock pro and president of the McGuane Park Advisory Council, there are two kinds of kids in the neighborhood:

The younger kids who don’t do much more than hang out near the parks, smoking dope and flashing signs.

“The wannabes,” Bailey says.

They're the kids who are on their way to a life of trouble, Breunig says.

“And then you have full-fledged gang members who are recruiting, who are dealing, who operate through the park,” he says.

You might catch the full-blooded gangbangers dealing on the basketball courts and shooting.

Since the neighborhood watch set up in the area, Breunig says, it seems gang members aren’t as confident when they roll through the parks on foot.

“The park is not a place where they feel welcome anymore,” Breunig said. “Not that they won’t pass through the park … They just don’t set up shop here.”

From Poplar, the watchmen spot the boys heading toward the west edge of the park.

Just after 9 p.m., the boys flash gang signs at the SUV.

“Call the police,” Breunig says.

Bailey pulls out his cell phone and dials 911.

“Yes, sir. I’m driving on 29th and Poplar Avenue — actually 30th and Poplar — on the south end of McGuane Park, and there’s around eight to ten young Hispanic, white and black males. They were flashing gang signs."

“We'll send someone,” the officer says.

“Thank you,” Bailey says.


At 9:05 p.m., the scanner buzzes to life.

Dispatch is sending police to two locations: a house in the 3500 block of South Wallace — and 30th and Poplar, where the boys are hanging.

“They look like they’re meeting there for something, doesn’t it?” Breunig asks.

“Yep,” Bailey says. “Something's gonna be going down.”


Before the night begins, first things first: Caffeine.

The watchmen pull up to the Dunkin Donuts at 749 W. 31st St. Inside the shop, Bailey waves to some neighborhood guys he recognizes. They sit in the corner over cups.

A towering man, Bailey is kind of neighbor that’s makes you consider two things: 1.) He’s a good guy to have on your side, and 2.) If he wanted to, he could snap you in half like a stiff board.

His friends claim he’s the neighborhood’s friendly giant, though.

“I’ve never seen him mad,” said Jaramillo, a 60-year-old truck worker at Budweiser.

Bailey got into the watch game not long after he experienced what it was like to live next door to a rowdy pack of gangbangers blasting music all night and dragging trouble home.

Things got better when they left the block.

“They moved,” Bailey said. “One of them got arrested for attempted murder. Another got arrested for murder.”

Today, Bailey is a gangbanger's worst nightmare.

"They know my car from a mile away, man," Bailey said.

The watchmen order up their fuel: a medium black coffee for Breunig, a large ice coffee for Bailey, and medium pumpkin spice for Jaramillo, who also orders a donut — glazed double chocolate.

Outside Dunkin Donuts, Breunig walks next door to CVS, a place known for vagrants loitering outside and gangbangers preying on the store's shorthanded security.

“When they don’t have police, gangbangers have a tendency to go into the store and just help themselves,” Bailey says.

Breunig peeks inside. All seems well.

Cups in hand, the watchmen hop in the SUV and hit the road.

Bailey tunes a police scanner to the Deering District’s frequency. The scanner tells the watchmen where cops are patrolling in the area.

Sometimes, the watchmen find themselves on location when crime strikes.

“Last Friday, we come to a burglary at 35th and Emerald,” Bailey says. “We beat the police.”

The watchmen did what they call a “drive-by” — just in case any suspicious characters stuck around.

“It’s not like you’re going to stop and get out and chase,” Breunig says. “But if you see something, you can call it in… That’s the last thing you want to do is get in the middle of something.”

The watchmen once stumbled into some undercover officers near a drug house in the 3700 block of South Wallace.

Bailey and the boys pulled up and gabbed.

“Told them, 'We’re the neighborhood watch,' ” Bailey remembers. “He said, ‘We know… we’ve been watching you watch this house.’”

Just before 9 p.m. the watchmen roll into the 3100 block of South Princeton — where families have been worried about a house where shots have been fired — to check for any unusual activity.

The block looks quiet tonight. A few people stroll past houses with neighborhood watch signs in the windows. One neighbor tracks the SUV with his eyes.

“I don’t mind getting the stink eye,” Breunig says.

The watchmen turn down 33rd Street and head toward Armour Park to make sure there’s no trouble brewing.

In the parking lot across the street from U.S. Cellular Field sits a Chicago Police wagon.

A man is standing in the park alone. It’s unclear what he’s doing.

“Are they throwing a boomerang?” Breunig asks.

No. The man’s doing a yoga-style exercise, outstretching his arms as if he’s throwing something.

The watchmen roll past Turtle's and Cork and Kerry and to make sure people aren’t stumbling out of the joints and getting into their cars.

It’s a slow night at the taverns. “I’ve never seen it that empty,” Bailey says.  

“That place is usually packed,” Breunig says.

In the 3800 block of South Emerald, Jaramillo shines the beam of a flashlight on an abandoned building to make sure nothing’s stirring inside.

In the alley of the 3900 block of South Emerald, the watchmen discover fresh gang graffiti on a garbage can: a pitchfork.

Bailey writes a note in the log. He’ll inform the city next week.

Breunig soon points the nose of the SUV toward the west side of the neighborhood.

Near Armour School, in the 900 block of West 32nd Place, the watchmen check out a house with a pitchfork spray-painted on its satellite dish.

This awkwardly narrow block is known for gang problems and violence. This is where, in June, a 17-year-old boy named Jeremy Salinas stood on the corner with a group of friends before he was fatally shot in his chest.

This night seems quiet enough. 

The watchmen spot a burnt-out streetlight. Bailey makes another note in the log book.

Since the neighborhood watch started five years ago, more than 500 broken streetlights have been repaired throughout this storied slice of the 11th Ward.

“Last count,” Bailey says, “I think it was 582 lights.”

Near 27th Street and Senour Avenue, the watchmen check on a fence behind Henry Palmisano Park. Bailey put a lock on the fence to stop neighborhood kids from trespassing onto city property to party in the woods near the fishing pond.

“Looks like they tried to get at it again,” Bailey says.

The watchmen drive down Halsted, past the front of the park, a large hill called Mt. Bridgeport, where decorative Buddha heads dot the grounds.

“There’s only two of them left,” Bailey says.

Someone snatched one of the Buddha heads.

“I don’t know what you could do with those,” Bailey says.


In an alley near the southern edge of McGuane Park, it appears the group of boys has grown.

“Something’s going down tonight,” Bailey says.

“Yeah," Breunig says. "They’re meeting in the park for something."

The police aren’t too far away. The watchmen soon pass an unmarked police SUV sitting on West 29th Street — the other side of the park.

“Stop him,” Bailey says.

Bailey gets out of the car and tells the police officer about the boys in the alley on the other side.

“He thought they were on this end,” Bailey says.

The cop turns the SUV around and drives down Poplar. As he closes in on the boys, he flips on his police spotlight, illuminating the troublemakers.

The boys scatter.

“They’re running!” Breunig says. “Yeah!”

“There ya go!” Bailey says, watching the boys run and hide. “All right, I salute you officer.”

It's 9:44 p.m. when the watchmen end their volunteer night shift.

This neighborhood watch is a successful one. There is a busted streetlight and fresh graffiti in the log book and the boys are running scared.

“Shook ‘em up a little bit,” Bailey says.

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