"Jack" and "Abby"

"Jack" and "Abby" are a homeless couple who live on Lower Wacker Dr.

The Chicago Police Department’s Homeless Outreach Team maintains more than just law and order on the streets underneath New Eastside. Visiting the dark thoroughfares at least once a day, the four-person squad mixes compassion, counsel and respect to pursue a mission that is unlike any police effort in the country.

“We try to all work together,” says officer Bob Bullington, a man of exceptional kindness who has been on the Chicago Police Department’s Homeless Outreach Team for nearly a decade. “The whole thing is to make it a happy medium between, you know, respecting the homeless’ rights, but yet the residents’ rights and the tourists’ rights, too.”

While the team looks for and responds to evidence or allegations of illegal activity on the lower streets, their regular efforts are part of a community-driven wellness campaign.

“We are here to assist various city agencies, church groups, condo associations, merchants associations, businesses, residents,” he says.

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The CPD's Homeless Outreach Team (left to right: officer Bob Bullington, Officer Jeannette O'Brien)

Equipped with the power to summon welfare shelters, rehab facilities and charity organizations in a single phone call, the team offers street-dwellers a way out that does not involve going to jail or visiting the emergency room.

“We try to figure out what their situation is without prying too much and ask them, you know, if they’re staying, if they want help,” Officer Bullington continues. “We can to talk to Family Services or find out where a shelter’s at or how to get some clothing or food or even how to get into rehab. If they want the advice, they take it. If not, they walk away.”

On Thursday mornings, the team joins the Department of Family Services & Support and the Department of Streets & Sanitation in a subsection of their beat officially known as the “Lower Wacker Drive Area (LWDA),” which is more or less the subterranean New Eastside.

Together, they conduct the weekly “Off-Street Cleaning” process, a checkup to make sure that all homeless in the area adhere to rules specifying exactly what items they may possess and where they may store them.

The LWDA and Off-Street Cleaning process are part of the 2015 Bryant Settlement Agreement. Crafted and signed by lawyers representing the City of Chicago as well as 16 homeless people who claimed that the city had illegally seized and destroyed their property, the Bryant Agreement includes a commitment to “respecting and protecting the rights of homeless persons.” Its sole exhibit — titled, “City Policy and Procedures Governing Off-Street Cleaning” — is the foundation of Chicago’s unique approach to homelessness in New Eastside.

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The exhibit states that “homeless persons” are entitled to “keep only ‘portable personal possessions,’” including a sleeping bag or bedroll, two coats, two pairs of shoes, not more than five blankets, and not more than three bags.

“From October through April,” it adds, “homeless persons may have up to five additional blankets and one additional sleeping bag or bedroll.”

“Every Thursday morning they come out here and tell us what we can have, how we can have it, and where we can be,” explains Jack, who lived on the 300 block of E. Lower Wacker Dr. with his wife, Abby, for most of the summer. “As long as it looks good, they’ll keep moving.”

Jack and Abby are 20-somethings who met in the high school of an upscale western suburb where they both used to live. He is the adopted son of a successful professional couple. She is the only child of a mother and a stepfather who, she says, took them “on his journey across the country to hide from every law enforcement agency possible.”

Jack works for a bicycle courier service and stores his transport across the street. Abby panhandles at the intersection where Wacker Dr. meets Lake Shore Dr. and does her best to sell her paintings of “bubbles and polka dots and landscapes.” They store their savings in a bank safety deposit box and hope to move into an apartment before winter. 

According to Officer Bullington, Jack and Abby are “nice people” who are “just passing through, trying to get (their) lives together.” They are also typical of a national trend, he continues, that makes today’s homeless population different from the one he encountered nearly a decade ago.

“What we’re seeing down here, it’s not the chronic homeless person,” he explains. “The people are in their mid-20s, you know, and already been through every family member and burned every bridge. For some reason or another they end up in downtown Chicago. A lot of them have families. That’s the sad thing. A lot of them have children.”

Although the team still encounters mentally ill people and arranges for them to be transferred to the proper facilities if they appear likely to cause harm to themselves or others, he believes that “most of them are really down on their luck… Bad choices in life, bad relationships, bad career moves.”

This benefit-of-the-doubt approach has helped the team achieve positive results. Officer Jeannette O’Brien, a 20-year veteran, recalls a day last spring when a homeless person they visited regularly asked for help getting into a rehab program.

“He was ready to go,” she remembers. “He actually approached me because one of the other homeless had told him, ‘You should talk to homeless officers because they can get you in.’ I said, ‘We can make it happen today, if you’re ready to go today.’”

A few weeks ago — when she saw the man at a convenience store and learned that he had kicked his drug habit, moved in with his girlfriend’s parents and is enthusiastically seeking employment — the incident became one of her greatest achievements on the job.

“He said, ‘I woulda been dead or in prison if you didn’t get me in rehab that day.’”

Note: the names of the homeless persons described and quoted in this story have been changed to protect their privacy.

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