Joshua Gray, a South Shore resident with a background in municipal politics, education and activism, is running for alderman of the 5th Ward, saying his professional experiences position him well to perform alderperson's roles in policy and constituent services.
He is a former aide to South Side Ald. David Moore (17th) and is particularly interested in legislating on council, proposing reforms to the local governance and community relations of police districts and the city's rules regarding developers' set-asides for affordable housing.
Gray said he had been getting calls from others when Ald. Leslie Hairston (5th) announced her retirement. "Me assessing the situation and the people I was talking to, I felt like no one's better for this position than me, because of my experience," he said.
Outside of formal politics, Gray has worked as an anti-violence community organizer for the Rev. Michael Pfleger, the priest and longtime social activist of Saint Sabina Church in Auburn Gresham, working in event and protest action logistics and planning. After the birth of his first child, he pivoted to working in education, beginning as a dean at the charter school Chicago Bulls College Prep, 2040 W. Adams St., and then as an assistant principal at the Chicago Public School Sarah E. Goode STEM Academy, 7651 S. Homan Ave.
"It turned out I didn't want to be a principal," he said. So he went into educational advocacy for the KIPP Chicago charter school network, which gave him experience in lobbying legislators.
In 2018, Gray made a first run for public office upon the retirement of longtime Cook County Commissioner Jerry Butler (D-3rd), placing fourth in a field of seven candidates with 9.61% of the vote. (Now-Commissioner Bill Lowry won with 33.29%.)
After the loss, he took a job as Moore's assistant. He was a body man, accompanying the Englewood alderman to community and government events.
"He taught me a lot," Gray said, calling Moore an alderman who got things done in council and in terms of constituent service. He said Moore "shows up to everything" in his ward and said he would should he be elected alderman, too.
"Father Pfleger used to tell me 'a shepherd needs to smell like sheep.' If you're a community person and people don't see you, you're not around, you're not at meetings, you don't have anything to add on, then you don't smell like sheep," Gray said.
Gray eventually became Moore's ward organization political director and ran his 2019 reelection campaign. (Gray was also 2019 mayoral candidate Amara Enyia's campaign manager.)
He has been doing political consulting ever since; his clients have included Ald. Leslie Hairston (5th), state Sen. Jacqueline Collins (D-16th), state Rep. Mary E. Flowers (D-31st) and former Cook County Commissioner Richard Boykin (D-1st) during his 2020 race for clerk of the county Circuit Court.
During this time, he also worked for community organization South Shore Works on COVID-19 vaccine outreach, planning regular events where people could get shots and informational canvassing.
Gray said his experience in education gives him charisma and good managerial experience, the latter of which comes in handy when staffing a ward office. He said working at a ward office is a customer service job — answering the phone, connecting with city departments, following up — and said he would make his hiring decisions based on those skills as well as their commitments to the ward.
Noting that an alderperson and their staff can’t fix things like the roads alone, he said he has made a career out of being a people person who can work with people with whom he doesn't agree. He wants to find middle ground and thinks he can, but added that if an alderman isn’t getting services constituents need from the city, “then you need to ruffle some feathers.”
A former chairman of the controversial Cook County Juvenile Temporary Detention Center, Gray said the most prominent issue he will face if elected is public safety, calling violence a result of poor municipal policies in education and job creation. He said Chicago Police Department commanders are not accountable to alderpersons who represent their districts and would like to change policy to allow alderpersons to hire commanders.
"That would give them accountability to aldermen, because if something happens in our ward, it's our fault," he said.
He would also like commanders to have a minimum period of service in their districts, noting the revolving door in leadership in some police districts as commanders get promoted or transferred.
Gray said the Chicago Alternative Policing Strategy, or CAPS — the district's foremost community engagement strategy, in which police liaisons, beat officers and commanders hold regular community meetings in precincts — needs a "facelift." Police could do a better job knowing the blocks they patrol and form more genuine personal relationships with civilians.
As a former renter, Gray said "quick price hikes are ridiculous" and that big developers need accountability, which he suggested he could do with a bully pulpit.
"You not saying nothing is you allowing (developers) to do whatever they want to do," he said. "As an alderman, you have a loud voice. … I can be loud so you have to address me."
He said Chicago's Affordable Requirements Ordinance, which requires developments with 10 or more units that get council approval for entitlement, city land purchase or financial assistance set aside a portion of units as affordable housing. In lieu of the set-aside, however, developers can (and often do) pay a small fee into the city’s Affordable Housing Opportunity Fund.
"These people are filthy rich," Gray said of developers. “We need to stop giving them the easy way out."
Gray is interested, however, in courting commercial interests and entrepreneurs to finance new developments in the ward, noting that aldermen should be trying to attract these entities to the ward at meetings, networking events and other functions.
"You have to get them to understand: they only see the bad side (of the South Side) on the news in terms of crime. But there are a lot of good people in these neighborhoods that have great jobs," he said. "And they need services."
"We don't have the basics in South Shore," he said. "I think Hyde Park, 53rd Street, is a great example, but Hyde Park is not South Shore, is not Kenwood, is not Woodlawn. There's different needs in different neighborhoods. I would not be a unilateral alderman; I would have to talk to the people and figure out what they want and how to work together to bring it here."
Gray grew up in Hyde Parker and attended St. Thomas the Apostle School, Kenwood Academy and Sam Houston State University in Huntsville, Texas. He's a father of four, all of whom attend Chicago Public Schools, and lives in the Jackson Park Highlands.