American Express Sues Chikoo Patel as CKO Real Estate Unravels

Chikoo Patel is drowning in debt.

American Express is the latest among a slew of lenders going after the embattled Chicago landlord in Cook County court, citing an unpaid credit card balance of over $63,000 following a missed minimum payment earlier this summer, according to a lawsuit filed last week.

It’s a small dollar figure compared to the scale of his real estate collapse, which so far includes about $20 million in alleged debts or broken contracts across Illinois. But the new lawsuit shows how deep of a financial hole Patel has dug along his journey from up-and-coming investor to embattled defendant.

Patel’s profile was rising for years as a landlord and large-scale property manager in Chicago’s South Side apartment market. Through his company, CKO Real Estate, he acquired and took on management for dozens of rental buildings in neighborhoods like South Shore. He brought in outside investors to help bankroll acquisitions, promising steady returns, while positioning himself as a key player in affordable housing. For a while, the strategy worked, until tenants, and then lenders, began to see the cracks.

Now, at least one of Patel’s frequent investment partners, Shai Wolkowicki, is distancing himself from the financial turmoil.

“We have not been associated with Chikoo Patel or CKO Real Estate since the beginning of February, when we parted ways. We have had new management in place since that time,” Wolkowicki said in an email. He didn’t provide an interview or respond to follow-up questions about the path to recovery for his investments or the size of his and CKO’s real estate portfolio.

Patel didn’t return multiple requests for an interview.

Buildings under CKO’s control deteriorated, and financial woes followed. Wolkowicki has been named a defendant along with Patel in a $16 million lawsuit brought by Old National Bank over a Springfield multifamily deal that has sunk into distress. Wolkowicki also took over decision-making authority from Patel for Rockford properties as they were sold off earlier this year, according to a person familiar with the transactions.

At CKO’s Chicago buildings, maintenance requests went unanswered. Mold, pests, broken heating systems and unsafe stairwells became common complaints. This spring, tenants organized and took their fight public. South Shore renters pleaded with city officials to be released from their leases, saying they felt scammed out of rent and deposits while Patel’s team ignored basic repairs. One resident told Block Club that living in a CKO building felt like being “trapped,” with no way out short of legal intervention.

The city eventually stepped in. In April, Chicago officials sued the owners of a South Shore courtyard building formerly managed by CKO, citing hazardous, slum-like conditions that posed an “imminent threat” to tenants. The city sought a court-appointed receiver to take over management and make repairs at 6952-58 South Paxton Avenue, where residents had gone without heat and hot water after CKO shuttered operations. Patel was summoned to court alongside the property owners and lenders, though he told the Triibe he hadn’t been associated with the buildings for “some months.”

As property conditions worsened, Patel’s financial troubles multiplied. Lender Itria Ventures, which provides small-businesses capital in exchange for pledging their future revenues toward repayment, sued CKO and Patel earlier this year seeking over $115,000 in alleged debt that fell into default, according to documents obtained by The Real Deal. CKO and its affiliates borrowed $150,000 a year ago in exchange for pledging to repay $192,000, but began missing payments by February, public records show.

Itria dismissed its lawsuit but appears to have plans to re-file it; an attorney for securitized mortgage lenders appeared in the case on behalf of entities that own property set to be seized from borrowers with ties to Patel. The loans on those properties, at 541 East 80th and 8100 South May streets in Chicago, totaled over $1 million and were originated by locally based lender Renovo Financial.

The revelations painted a picture of a multifamily operator stretched thin, using other people’s money to chase scale without the capacity to deliver.

By late summer, some of Patel’s investors and lenders joined the revolt. Last month The Real Deal reported that unpaid debts and broken promises soured once-supportive financial backers. Some had put significant capital into Patel’s ventures expecting reliable returns; instead, they ended up damaging a relationship with the Department of Housing and Urban Development and got left holding buildings that were bleeding cash, with tenants unwilling to pay rent under unlivable conditions.

Whether buyers step in with the capital and competence to stabilize the properties remains an open question. For lenders and investors, the cautionary tale is clear: chasing yield through lightly capitalized operators can backfire spectacularly.