The newest ward in Chicago — encompassing a good portion of the Loop, as well as Greektown, Fulton Market and a large swath of the Near West Side — is primed to become one of the most influential as it stands ready to become the center of the next wave of development.
But the two men vying to become the 34th Ward’s new alderman are unproven in the world of politics and government. One is a real estate developer who has twice lost bids for Congress and the other a well-known Navy veteran, former county prosecutor and son of a billionaire who failed to defeat Cook County State’s Attorney Kim Foxx two years ago in the Democratic primary.
The candidates — commercial real estate broker James Ascot and lawyer Bill Conway — are both pro-development and rank public safety high on their priority list.
Many of the similarities end there.
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At 73, Ascot says becoming alderman will be the culmination of his career, while some political insiders think the 44-year-old Conway, whose aldermanic bid is being partly funded by some of the biggest names in Chicago’s business community, aspires to use the City Council seat to climb to higher office. In addition to running for state’s attorney, Conway mulled a bid for mayor this year at the urging of some in the labor and business community, he told the Sun-Times last summer.
Regardless of what the future holds for the two men personally, development and how they’d tackle it is the main issue on the Feb. 28 ballot.
Downtown’s future — including along key corridors such as State Street, Michigan Avenue and LaSalle Street — is top of mind for both candidates as the area continues its rebound from COVID-19. Even major projects on the new ward’s fringes, including the Thompson Center’s transformation into a Google headquarters in the 42nd Ward and a first-ever Chicago casino in the 27th Ward, are likely to have an impact on the 34th in the coming years.
“I guarantee there will be no shortage of work” negotiating complex and large-scale zoning deals, said neighboring Ald. Brendan Reilly, 42nd, who has long been the Loop’s alderman but gave up some of his ward to form the 34th. He previously endorsed Conway for state’s attorney.
The areas between Van Buren and Kinzie and from the Chicago River to the Kennedy Expressway are the next rumored “hot spot” for development, Reilly said, because of its proximity to the Loop and Fulton Market.
Somewhat lost amid the excitement of the new 34th Ward is the fact that it was carved out of the Far South Side, as many Black residents who live in the neighborhoods have moved out of the city.
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As Chicago aldermen were redrawing the city’s maps, as they do every 10 years following the U.S. census, the 34th Ward was moved because incumbent Ald. Carrie Austin was not going to run for reelection as she faces federal fraud charges. She described her exit as a “sacrifice” for the rest of the city’s Black Caucus during the contentious remap process. For more than 35 years, the 34th was represented by the Austins: first, Ald. Lemuel Austin and, after his death, by his wife, Carrie.
[ Ald. Carrie Austin and chief of staff indicted on bribery charges for allegedly accepting home improvements from developer ]
Indeed, the new ward is unrecognizable compared with the last. The old 34th — overwhelmingly Black, with a median income lower than the city’s average — covered the Far South Side neighborhoods of West Pullman, Washington Heights, Morgan Park and Roseland.
The new 34th is majority white, wealthier than the city average, and centered around Greektown, as well as much of the University of Illinois at Chicago campus and Little Italy. It also has appendages stretching eastward into the Loop to include the west side of Michigan Avenue and as far north as Millennium Station. It also covers landmarks such as the Rookery Building and the Chicago Board of Trade.
As he campaigns across the ward, Ascot said he thinks Conway’s running for alderman to use the seat on the City Council as a steppingstone to higher political office.
“For me, this is a commitment,” he said. “… I’m not looking to be mayor, I’m not looking to be congressman. This is it.”
“I think a big part of Chicago’s future will be the 34th Ward, and that’s what I’m focused on in the present and the future,” Conway told the Tribune in response.
While both broadly agree on the ward’s major challenges and opportunities, their differences also emerge in their personal trajectories.
After his parents’ divorce at a young age, Conway grew up near the corner of Wellington and Sheffield avenues in Lakeview where, during campaign season, he recalled shaking hands with then-44th Ward Ald. Bernie Hansen. As a teen, he attended the prestigious Latin School, and worked at Tower Records and at the Securities and Exchange Commission, sorting microfiche. He went on to attend the Wharton School of Business at the University of Pennsylvania for his bachelor’s in accounting, Georgetown University for a law degree and then got his master’s in business from the University of Chicago, he said. He joined the Navy Reserve in 2012.
Shortly after his primary loss to Foxx in March of 2020, Conway was asked to be senior intelligence director at European Command Headquarters in Germany, where he stayed until December 2021, he said. During the pandemic, he also launched Green Street Renewables, a company he said helps downstate schools build solar arrays. He’s also taught finance classes at DePaul University, and is active in several investment ventures. If elected, he said, he would continue teaching but turn over the energy company to his partner.
Ascot emigrated from Greece with his family at age 9, and after graduating from Lane Tech, he studied psychology and went on to work as a therapist in Des Plaines after college and later at Loretto Hospital on the West Side. He told the Tribune he left the profession after about six years out of frustration because patients were being recommitted repeatedly. His sister got him into real estate, and he launched Ascot Realty in 1986.
He became president of the Chicago Association of Realtors in the mid-1990s and was a liaison with the National Association of Realtors in Washington, which he said spurred his unsuccessful congressional runs versus U.S. Rep. Danny Davis. He and Davis, he said, are on good enough terms that the congressman rented office space from him.
If elected, Ascot said, he plans to pass the real estate firm to his son Denis. The company mainly serves as a commercial brokerage, including in the West Loop. Ascot said he would recuse himself from voting on council matters that involve the firm and pledged real estate interests would have the “same access” as other constituents.
Ascot has received a $10,000 contribution from the Realtor Political Action Committee and thousands from others in the real estate world, including commercial firm Blue Star Properties, Michigan Avenue Real Estate Group founders Robert Judelson and Thomas Meador, and Vivify Construction, which has an active West Loop project. But he’s raised just $56,000 between September and mid-January, according to state campaign finance records. That sum includes a $12,000 loan from himself.
He has campaigned on governing with compassion, citing his mental health background and belief that housing is a human right. But he said there’s little room in the 34th Ward for fresh affordable housing developments, and argues the city’s affordable requirements ordinance, which regulates the construction of new residential projects, is too restrictive for developers.
Conway, meanwhile, has raised $425,000 since August. So far, he has not logged any contributions from his father, billionaire William Conway. The founder of the D.C.-based investment firm the Carlyle Group gave $10.5 million to his son’s unsuccessful state’s attorney bid, drawing accusations from Foxx’s camp that he was trying to buy the seat. Conway also had to answer for Carlyle’s ties to the military-industrial complex and a controversial for-profit nursing home chain.
The elder Conway is supportive of the campaign, but is focused on his work as interim CEO of his firm, the younger Conway said.
The rest of Chicagoland’s investment world has stepped up. Madison Dearborn Partners Chairman John Canning and his wife, Rita, each contributed $6,000 to Conway, as did MDP co-CEO Paul Finnegan and other partners. Grosvenor Capital Management CEO Michael Sacks, who was a close outside adviser to former Mayor Rahm Emanuel, gave $6,000, as did leaders at Citadel investment firm, the Duchossois Group’s Craig Duchossois, DRW Trading founder Donald Wilson, Jr., and investor Matthew Pritzker, a cousin of Gov. J.B. Pritzker. The governor last week also endorsed Conway.
While he says he’s “pro-economic development,” Conway said he would not be beholden to the business community.
“I don’t know why certain people give me money or don’t give me money,” he said. “I will say it would not affect my ability to say no to them.”
The Building Owners and Managers Association of Chicago, which represents big office buildings, has also backed Conway.
Its executive director, Farzin Parang, said Conway demonstrates that he “understands the importance of that revitalization of downtown,” in terms of addressing crime, convincing workers to return to the office, and “block and tackle things” that an alderman with so many business constituents have to deal with, such as permitting and regulation.
More broadly, “folks in the business community are looking for public servants who are reasonable, who understand you can’t have a well-functioning city without a thriving business environment, and are problem solvers willing to listen to folks” rather than lobbing “bombs,” Parang said.
Alongside money from the business community, Conway also has earned endorsements from progressive labor organizations, including SEIU locals and the Chicago Federation of Labor, and trade unions such as IUOE Local 150, which traditionally backs pro-development candidates. Recently retired Illinois Secretary of State Jesse White also endorsed Conway.
Both Ascot and Conway said they want to see more police presence in the ward, with officers who know and patrol the district regularly, and the two candidates argue a shortage of cops is contributing to crime.
The increase in homicides and shootings in the new ward’s police districts — the 1st and the 12th — were higher than the citywide average: The number of homicide victims rose from 20 in 2019 to 50 in 2022, a 150% increase. Citywide, the number of homicides climbed 40% in the same span, according to the city’s violence reduction dashboard. The percentage of shooting victims nearly doubled in the two police districts compared with 33% citywide, according to city statistics.
Those districts have 131 fewer officers compared with January 2019, according to staffing data tracked by the city’s inspector general. Neither Conway nor Ascot supports a broader “defund the police” movement, and both pledged to address the root causes of crime and support nonpolice responses to mental health emergency calls.
Both are opposed to raising the real estate transfer tax to create a dedicated funding stream for homeless services, arguing the tax could deter sorely needed development.
Ascot said he wouldn’t support a hike until he understood the city’s current spending priorities. Conway said he wanted it to be easy for redevelopers to work in the Loop when it comes to “permitting, zoning,” and “potentially,” incentives such as tax increment financing. Asked whether adding affordable housing to the Loop is a priority, he said, “We have to see how individual projects pencil out.”
One standout proposal from Conway is to create a new high school to serve West Loop families who will have children graduating from Skinner West Elementary.
“Not everybody can go to Whitney Young and St. Ignatius,” he said, and the feeder high school — Wells Community Academy at 936 N. Ashland Ave. — is not close and needs improvement. CPS statistics show Wells’ graduation and college enrollment rates are below district averages.
“I really want to make sure that I, my family and the folks in this area are living in a stronger, safer community,” Conway said.