Updated: 6:18 p.m.
For more than two decades, Chester Wilson Jr. has been the top aide to powerful Chicago Ald. Carrie Austin, a position that pays a six-figure salary and often brings him into close contact with many of the most important people in the city’s Democratic politics.
In addition to his job as Austin’s chief of staff, Wilson also became something of a player in his own right — in real estate on the far South Side. At one time, he listed ownership of nine properties in or near Austin’s 34th Ward.
But Wilson fell far behind on his property taxes for some of his buildings. He came to owe tens of thousands of dollars in taxes, interest and fees for just one dilapidated building at the corner of 103rd Street and Corliss Avenue, having skipped property-tax payments for every year from 2008 through 2013.
Then a businessman named Boris Nitchoff stepped up and bought the unpaid taxes for a few hundred dollars at Cook County’s scavenger tax sale in 2016. That gave Wilson three years to pay his tax debt, or he could have lost the building to Nitchoff.
Instead, Wilson was able to hand the building over to a county agency, in a move that wiped clean more than $150,000 in unpaid taxes for the property, according to documents obtained by WBEZ.
Now, both Wilson and Nitchoff have drawn the attention of the federal authorities who raided Austin’s ward office three months ago. A grand jury subpoena in the ongoing, wide-ranging probe shows investigators wanted to see “all items related to” not only Austin but also Wilson, Nitchoff, three Nitchoff relatives and five Nitchoff family companies.
Nobody has been charged with a crime, and Austin has denied any wrongdoing, continuing her 25-year tenure as one of the most influential African American members of the City Council.
Nor is it known what suspicions drove FBI agents to get the search warrant used to raid Austin’s office on 111th Street on June 19, when they dramatically hauled away boxes of documents and computers in the middle of a weekday.
At City Hall recently, Wilson declined to comment on either the investigation or his problems with the property on Corliss, saying, “You know I can’t answer that.”
Austin did not respond to messages seeking comment, and neither did Boris Nitchoff.
But a WBEZ investigation found the connection between Wilson’s private property dealings and Nitchoff, whose family’s company has been among the top contractors in Austin’s ward for many years.
And public records also detail how Wilson, 53, steadily and quietly rose from criminal convict who could not get hired as a cop to one of the highest-paid aides in the Chicago City Council.
"Perfect place for Chester"
Known to many at City Hall as a quiet but influential behind-the-scenes figure, Wilson was called upon to lead orientation sessions for the chiefs of staff of other, newly elected aldermen.
A lifelong South Sider, Wilson graduated from Corliss High School in 1984 and was working as a security guard at the Wrigley Building and the Chicago Sun-Times building in his early 20s, according to state Prisoner Review Board documents. He dreamed of becoming a Cook County sheriff’s deputy, even taking the hiring exam.
“But a one-time mistake would derail his dream of joining law enforcement,” his lawyer wrote in Wilson’s successful petition for executive clemency in 2013.
That mistake? A guilty plea in Cook County court in 1993 to a felony count for allegedly helping cover up the theft of a car.
According to his clemency petition, Wilson agreed to keep a car at his home at the request of his cousin. The car had been reported stolen, and Wilson put different license plates on the car. Wilson later argued that he did not know the car was stolen and had changed the plates to keep his landlord from reporting an unknown vehicle on his property.
“Concerned that he would lose his job if he kept missing days from work, Chester simply agreed to plead guilty to (one count) to put an end to the case,” his lawyer wrote in the clemency petition.
He was sentenced to 18 months probation, and the conviction frustrated Wilson’s plans of becoming a sheriff’s deputy. So he took another path that would prove fruitful.
“He started volunteering with the office of 34th Ward Ald. Carrie M. Austin,” his lawyer wrote. “Recognizing his dedicated spirit, they soon hired him as a part-time employee.”
Wilson became a full-time city worker in 1995 and was promoted to chief of staff within a few years.
“It turned out that politics was the perfect place for Chester,” his lawyer wrote.
Posing with Daley, other big Democrats
Wilson’s petition for clemency — which was granted in 2014 by then-Illinois Gov. Patrick Quinn, a Democrat — is heavy on references to Wilson’s political connections.
The petition included photos of Wilson with former Chicago Mayor Richard M. Daley, former Illinois Senate President Emil Jones (D-Chicago), Illinois Secretary of State Jesse White and Austin. Wilson also got letters in support of his clemency petition from two Illinois lawmakers, state Sen. Emil Jones III (D-Chicago) and state Rep. Bob Rita (D-Blue Island).
Austin effusively praised Wilson in a character letter to Quinn, referring to him as her “first line of defense ensuring my safe insulations when dealing with the general public.” The alderman also spoke on Wilson’s behalf before the Prisoner Review Board.
“I can substantially attest to Chester Wilson’s rehabilitation,” Austin wrote to the governor. “Mr. Wilson’s position allows him direct interaction with many elected officials, dignitaries, business and community leadership, and constituents.”
Wilson was Austin’s top aide during her 12 years in charge of the City Council’s important Budget Committee, which approves the city government’s annual, multi-billion dollar spending plans. Austin lost that coveted spot after Lori Lightfoot became mayor earlier this year.
Lightfoot gave Austin a consolation prize, appointing the veteran alderman to lead the new Committee on Contract Oversight. Wilson moved with Austin to the new committee three months ago, for an annual salary of a little more than $118,000, records in his city personnel file show.
But the Lightfoot administration blacked-out a section titled “references” in Wilson’s application for the new committee job. City officials argue that releasing his references would be “an unwarranted violation of the personal privacy of those individuals.”
WBEZ has filed a pending lawsuit against the city seeking the deleted parts of Wilson’s personnel file, alleging violations of the state’s open-records law.
"Prudent financial manager"
Besides the support of Democratic politicians, Wilson benefited from another letter for his clemency case from John Powen, a lawyer and real-estate developer from Deerfield. Powen’s company built a new house that Austin bought last year. Federal investigators had sought documents relating to the construction and sale of the house.
Powen did not return messages seeking comment for this story.
Wilson also boasted in his clemency petition of success in the real estate field: “As a prudent financial manager, Chester now owns several properties.” The petition included copies of some property-tax bills that Wilson had paid.
What his lawyer did not describe, though, was how Wilson often struggled with keeping up with the property taxes for some of his other buildings. The city of Chicago also cited Wilson repeatedly for code violations, including locking out tenants, letting dumpsters overflow and doing construction without permits.
One of the longest and most complicated sagas involved Wilson’s two-story brick building at 10300-02 S. Corliss Ave.
Wilson had paid $200,000 for the property in 2005, taking out a mortgage. But he filed for bankruptcy protection, listing that mortgage among his debts, in 2010.
He also got out of paying the property taxes there. For the years 2008 through 2013, the tax debt on the Corliss building amounted to more than $94,000 when officials finally offered the building at the county’s scavenger sale in 2016.
A company called B. Hartman Group LLC bought the taxes for the Corliss building for $500, the minimum bid, at the county’s scavenger sale. The owner of B. Hartman Group is Boris Nitchoff, records show.
Still, Wilson had to pay the back taxes, plus interest and fees, to Nitchoff within three years, or Nitchoff could have taken the property.
But Nitchoff would never acquire the building, which included ground-floor retail space and second-story apartments.
Nitchoff’s move instead gave Wilson time to come up with a different solution to his problem on Corliss Avenue.
A "donation" wipes away tax debt
This path involved the Cook County Land Bank Authority. The county created the agency and gave it the power to take tax-delinquent properties and give them to new owners, who are supposed to improve them and put the land back on the tax rolls.
As Austin’s chief of staff, Wilson had frequent contact with the land bank, according to emails obtained by WBEZ, about a variety of properties. Much of the land bank’s work is done in the 34th Ward, which includes parts of West Pullman, Roseland and other economically challenged neighborhoods on the far South Side.
In the case of the Corliss property, Wilson offered a “donation” of his own building to the land bank, according to one email from an official of the land bank to Wilson in 2017.
The land bank’s acquisition of the building from Wilson wiped out the property’s huge and growing tax debt. By that point, the back taxes, interest and fees on the Corliss building topped $150,000, according to WBEZ’s analysis of county records.
Wilson not only gave the land bank the property — he also identified a potential buyer. In an email from his official city account, Wilson told an official with the bank that it could sell his building to Lisa Livingston. She’s the owner of a day care center in the south suburbs.
And records show Wilson had done business with Livingston before the Corliss deal with the land bank. Wilson and Livingston bought a house together in the 9700 block of South Emerald Avenue in 2016, and the rehabbed house was flipped for a tidy profit the following year. Powen, the developer who built Austin’s house, notarized documents related to the Emerald deal, according to public records.
In May 2018, two months after Wilson gave the building on Corliss to the land bank, the county sold it to Livingston for $20,000.
The land bank’s executive director, Robert Rose, did not return calls seeking comment. But in a statement sent to WBEZ after publication of this story, Rose said the land bank does not allow deals if there is a "prior relationship or affiliation" between the previous owner of the property and the prospective buyer.
"In the event that fraud is detected, the Cook County Land Bank Authority can reclaim the property, and any back taxes that were extinguished may be reinstated as due payable from the original owner," Rose said.
Livingston said she has a business relationship with Wilson but was unaware that Wilson previously owned the building on Corliss — or that Wilson recommended her to the land bank — until a reporter told her that this week.
The land bank gave Livingston a year to fix up the building. But on a recent visit, it remained boarded-up and in obvious disrepair.
In February, the city sued Livingston in Cook County Circuit Court because, officials said, they wanted to fix “dangerous and unsafe conditions at the property” on Corliss.
But land bank officials granted Livingston’s request for an extension until December to wrap up the repair work on the building.