Ken Griffin takes a 44% loss selling 2 Chicago penthouses he never lived in as he moves to Florida

• Ken Griffin has sold two Chicago penthouses for about 44% less than he paid.
• A representative for Griffin has said that his real-estate investments in Florida make up for the loss.
• Like Griffin, other wealthy people have left Chicago, due in part to hefty taxes and crime rates.

Ken Griffin, the billionaire founder of the hedge fund Citadel, has found buyers for two of his four luxury apartments in Chicago.

Griffin sold the top two floors at a condo building in the wealthy Gold Coast neighborhood near Lake Michigan for a total of $19 million, The Wall Street Journal reported, citing property records.

Cook County records show that Griffin paid about $34 million for both units in 2017: $21 million for the 7,500-square-foot, six-bedroom top floor and $12.7 million for the one below, which has five bedrooms. That means he took about a 44% loss on the sale.

Both units, located atop the No. 9 Walton building, are unfinished, and Griffin has never lived in them.

The move comes as Griffin moves both Citadel and his own personal residence to South Florida.

A Citadel spokesperson told Bloomberg in October that the loss was a minor setback in the context of his other real-estate purchases.

"While the value of Ken's properties in his former hometown may have declined, thankfully it is only a small loss compared to the appreciation he's enjoyed on his property investments in Florida," Zia Ahmed, the spokesperson, said.

Griffin spent about $169 million on properties in Miami Beach's exclusive Star Island neighborhood between 2020 and 2023. In 2022, he spent over $100 million on two bayfront houses in Coconut Grove, an affluent Miami area. He has also amassed 27 acres in Palm Beach over a decade for about $450 million.

Griffin and the listing agents for the Chicago property did not respond to requests for comment sent by Business Insider last month.

Brokers said Chicago's luxury-real-estate market has flagged

The relatively lower sale price for Griffin's Chicago property is somewhat unsurprising, area real-estate agents said.

Michael LaFido, a broker, said superprime properties, which he described as $10 million or more, were a rarity in Chicagoland. In 2023, he added, only four properties sold for that amount.

Meanwhile, in Miami, 55 properties over $10 million were sold in the second quarter of 2024 alone, said the real-estate-consulting company Knight Frank's global report on superprime properties.

Rafael Murillo, a Compass agent in Chicago, said properties that cost eight figures were not a regular occurrence.

"We're just a much more affordable luxury market compared to Miami or New York," he said.

Murillo cited another luxury property that sold at a loss this year: a 6,100-square-foot condo in the city's St. Regis tower that was purchased for $8.2 million in 2021 and sold for $7 million in April.

Marquee listings in the suburbs have also seen price cuts. Basketball star Michael Jordan's mansion in Highland Park finally sold in September after going on the market in 2012, per its Zillow listing. Jordan listed the property for $29 million in 2012. It was most recently priced at $14.9 million.

Other wealthy homeowners are selling their Chicago properties

Griffin is one of several wealthy Chicago homeowners offloading their luxury properties at a loss this year, Bloomberg reported in March.

It said the city's hefty taxes and high crime rates had driven many of Chicago's richest residents to sell and relocate to other cities, including Miami and New York.

"The decline in value of Chicago real estate is representative of the failed political leadership in Illinois which is a loss ultimately borne by the people of the state," Griffin said in a statement to the Journal.

In 2017, Griffin purchased the Chicago penthouse, along with three other units in the same building, for a total of almost $59 million — the biggest real-estate purchase in the city's history, the Chicago Tribune reported.

The two remaining units in the record-breaking buy are still available for sale.

Many wealthy residents first fled Chicago to its suburbs during the COVID-19 pandemic, then left Illinois altogether, LaFido told BI.

He said that many homebuyers who can afford a property over $10 million aren't in Chicago anymore — leaving sellers like Griffin to take the financial hit.

"If you're going to build something $5 million or more in Chicago," LaFido said, "you're going to take a loss."

This story was originally published on October 21 and updated on November 13.

Correction: October 22, 2024 — A reference to Chicago's "mansion tax" has been removed from this story. Chicago voters in March rejected a proposal for a one-time real-estate tax on properties valued at over $1 million.