Billionaire hedge fund manager Ken Griffin, founder of Citadel and Citadel Securities, has faced significant financial setbacks in Chicago’s luxury real estate market, with losses nearing $30 million from the sale of his high-end condominium holdings.
The most recent transaction, a $15.9 million sale of the 35th and 36th floors at No. 9 Walton Street, marks the completion of his divestment from a once-record-breaking $58.75 million purchase in 2017.
These real estate losses, combined with mounting regulatory pressure and allegations of illegal market practices from retail investors and public figures, including criticism from Trump Media, paint a complex picture of Griffin’s current financial and reputational challenges.
Chicago Real Estate: A String of Multimillion-Dollar Losses
Griffin’s exit from Chicago’s luxury real estate market has been marked by steep financial losses, reflecting both personal strategic shifts and broader market dynamics.
His relocation to Miami in 2022, along with Citadel’s headquarters, prompted a sell-off of his Chicago properties, many of which were sold at significant discounts compared to their purchase prices.
Below is a detailed breakdown of his documented real estate losses in Chicago:
- No. 9 Walton Street Condos: In 2017, Griffin purchased the top four floors (35th through 38th) of the No. 9 Walton Street condo tower for $58.75 million, setting a record for Chicago’s most expensive home sale. These units, purchased unfinished, were never occupied by Griffin. His subsequent sales have resulted in substantial losses:
- 37th and 38th Floors: Sold in November 2024 to Illinois Governor J.B. Pritzker and his wife, MK Pritzker, for $19 million, a $14.65 million loss from the $33.65 million purchase price. This transaction was Chicago’s priciest residential sale of 2024.
- 35th and 36th Floors: Sold in April 2025 for a combined $15.9 million ($7.4 million for the 35th floor and $8.5 million for the 36th floor), down from the $24.6 million Griffin paid, resulting in an additional $8.7 million loss.
- Total Loss at No. 9 Walton: Approximately $23.35 million.
- Waldorf Astoria (37th Floor): In October 2022, Griffin sold a 7,400-square-foot unit for $10.225 million, a $3.075 million loss from the $13.3 million he paid in 2014.
- Park Tower (66th Floor): In January 2023, Griffin sold an 8,000-square-foot condo for $11.2 million, incurring a $3.8 million loss from the $15 million purchase price in 2012. The buyers were filmmaker George Lucas and his wife, Mellody Hobson.
- Cumulative Chicago Losses: With the No. 9 Walton, Waldorf Astoria, and Park Tower sales, Griffin’s total documented losses in Chicago’s real estate market approach $30 million.
These losses are part of a broader trend in Chicago’s high-end condo market, which has faced declining valuations due to economic pressures, shifting demand, and safety concerns.
For instance, a downtown Chicago condo sold in 2024 for $900,000, down from its 1989 price of $1.1 million, and billionaire Michael Krasny reduced the asking price for his Park Tower condo from $9.8 million to $6.9 million.
Griffin’s losses, while significant, are a minor dent in his estimated $46.5 billion net worth, as reported by Forbes in 2025.
Broader Real Estate Strategy: Shifting Focus to South Florida
Griffin’s Chicago sell-off aligns with his relocation to South Florida, where he has invested heavily in residential and commercial real estate.
Since 2022, he has spent over $1 billion in the region, including:
- Residential Purchases: A $106.9 million Coconut Grove estate from philanthropist Adrienne Arsht and a $157.5 million, 6.5-acre waterfront assemblage on Miami Beach’s Star Island.
- Commercial Ventures: A 4.2-acre assemblage in Miami’s Brickell neighborhood for Citadel’s new $1 billion headquarters, designed by Norman Foster, and two office buildings in downtown Palm Beach.
- Condo Buyout Speculation: In 2024, Griffin was linked to a potential condo takeover at Solaris at Brickell Bay, adjacent to his planned supertall headquarters, with nearly half the units sold to Delaware LLCs sharing the same manager.
Griffin’s South Florida investments contrast sharply with his Chicago losses, suggesting a strategic pivot to a market with stronger demand for ultra-luxury properties.
Miami saw 55 properties over $10 million sold in Q2 2024 alone, compared to Chicago’s more affordable luxury market.
Regulatory Pressure and Allegations of Illegal Market Practices
Beyond real estate, Griffin and his firms, Citadel (a hedge fund) and Citadel Securities (a market maker), face significant scrutiny from regulators and retail investors.
These pressures add a layer of complexity to Griffin’s financial narrative, as allegations of market manipulation threaten his reputation and operations.
Regulatory Actions and Fines
Citadel Securities has faced multiple regulatory penalties for trading violations, particularly related to its role as a market maker and its operation of a dark pool, a private trading venue that allows large investors to trade anonymously.
Notable incidents include:
- 2020 FINRA Censures: Citadel Securities was censured 19 times by the Financial Industry Regulatory Authority (FINRA) for violations including failure to close out fails-to-deliver (FTDs), naked short selling, inaccurate reporting, and executing trades during a market halt.
- 2023 SEC Settlement: The Securities and Exchange Commission (SEC) charged Citadel Securities for mismarking short sales as long sales between 2015 and 2020, leading to inaccurate trade reporting. The firm paid a $7 million penalty to settle the charges without admitting or denying guilt. [Source: SEC Press Release, September 2023]
- 2024 Cboe Fine: Citadel Securities was fined $3.5 million by Cboe Global Markets for failing to report certain options trades accurately, highlighting ongoing compliance issues. [Source: Reuters, March 2024]
These penalties, while relatively small compared to Citadel Securities’ revenue (estimated at $7.5 billion in 2024), underscore persistent regulatory concerns about the firm’s trading practices.
Critics argue that the fines are insufficient to deter misconduct, given Griffin’s wealth and the firm’s market dominance.
Retail Investor Allegations and Social Media Backlash
Retail investors, particularly those active on platforms like Reddit’s r/GME community, have accused Griffin and Citadel of systemic market manipulation, including naked short selling, spoofing, front-running, and misreporting trades.
These allegations gained traction during the 2021 GameStop short squeeze, where Citadel Securities’ role as a market maker for retail brokers like Robinhood drew scrutiny.
Posts on X have amplified these claims, labeling Griffin a “financial terrorist” and alleging that Citadel’s practices harm retail investors and pension funds.
Naked short selling, a practice where shares are sold short without first borrowing them, is a focal point of these accusations.
While naked short selling is illegal in the U.S. except in ‘limited circumstances’, retail investors claim Citadel exploits regulatory loopholes to depress stock prices, particularly for meme stocks like GameStop and AMC.
These allegations have fueled a vocal online movement against Griffin and his firms.
Also Read: Citadel’s motion to dismiss has now been denied in NWBO case
Trump Media’s Criticism
In 2024, Trump Media & Technology Group, the parent company of Truth Social, publicly criticized Citadel Securities for alleged naked short selling of its stock (ticker: DJT).
The company’s CEO, Devin Nunes, accused market makers, including Citadel, of engaging in “unlawful” trading practices that artificially suppressed the stock price.
Trump Media filed a complaint with the SEC, calling for an investigation into short-selling activities. [Source: Bloomberg, August 2024]
Citadel Securities denied the allegations, stating that its trading practices comply with all applicable regulations.
The SEC has not publicly confirmed an investigation, but the high-profile nature of Trump Media, backed by President-elect Donald Trump, has intensified scrutiny on Griffin’s operations.
The controversy aligns with Griffin’s political activities, including a $10 million donation to the Congressional Leadership Fund in July 2024, though he has not directly donated to Trump’s campaigns.
Also Read: Trump Is Now Taking on Illegal Short Selling After Threat
Chicago’s Market Challenges and Griffin’s Exit
Griffin’s real estate losses in Chicago reflect broader challenges in the city’s luxury condo market.
Since 2021, high-end properties have faced declining values, driven by:
- Crime Concerns: Griffin cited rising crime, including a colleague being robbed at gunpoint, as a reason for relocating Citadel to Miami. Chicago’s violent crime rate, while down from its 2016 peak, remains a concern for affluent buyers.
- Economic Pressures: Illinois’ pension crisis, with $37.2 billion in unfunded liabilities, and high property taxes deter investment.
- Limited Buyer Pool: Unlike Miami or New York, Chicago lacks a robust international buyer base for ultra-luxury properties, and Midwest buyers are less inclined toward lavish spending.
Griffin’s decision to list properties at below-purchase prices signaled his intent to exit Chicago, even at a hefty loss.
Real estate agent Nancy Tassone noted that price reductions are necessary to attract buyers in the ultra-high-end market, where demand is limited.
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Also Read: Investors now urge President Trump to investigate naked short selling in formal letter
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Griffin is up or down $30 million every hour of every investing day. He won’t be brought down until the federal gov’t starts investigating his companies’ violations of existing laws, like illegal naked shorting and spoofing, and then fine him 10’s of Billions of $$$, not the piddly $7M so far, and throw his ass in jail. let’s hope the new SEC Chair has the balls to do it, plus close FINRA down. It’s corrupt. Let the SEC do what FINRA is supposed to do, but never does, Ex. MMTLP.
Thanks for sharing your thoughts. I agree, time will tell if the new SEC is competent.