Billionaire Sells Off Entire Chicago Portfolio and Relocates to Florida

Billionaire Completes Three-Year Exit

Ken Griffin is finally done with Chicago. The billionaire founder of Citadel just found a buyer for his last property in the city, a 67th-floor penthouse he has owned for 25 years.

He moved his hedge fund to Miami in 2022, citing crime that included bullet holes in his building and colleagues robbed at gunpoint.

Since then, he has been selling off his Chicago real estate piece by piece, mostly at a loss. The timing of his exit is hard to ignore, because the city he left behind is now staring down a $1.19 billion budget deficit and floating the idea of charging residents $1. 25 for every package that lands on their doorstep.

The Penthouse Sells for $12.5 Million

Griffin’s condo at 800 North Michigan Avenue has gone under contract for $12. 5 million.

The six-bedroom, seven-bathroom unit spans 9,250 square feet on the top floor of Park Tower, one of the most recognizable buildings on the Magnificent Mile.

He bought it in 2000 for $6.9 million when the building was new. The listing price is about 20% lower than the $15.75 million he was asking in July.

If the sale closes at that number, it would be the most expensive single condo sale in downtown Chicago in at least three years.

Bullet Holes and Colleagues Robbed

Griffin did not leave quietly. In November 2025, he told an interviewer that 25 bullet holes were found in the front of his Chicago building. Two colleagues had bullets fly through their cars.

Another was robbed at gunpoint. One was punched in the head by a stranger while waiting for a ride.

Griffin compared Chicago to Afghanistan and said he could no longer tell recruits it was a great place to raise a family.

Dinner conversations in Chicago, he said, had become about crime and failed policies instead of the future.

Sold to George Lucas and the Governor

Griffin lost money on almost every Chicago property he sold.

He paid $15 million for the 66th floor of Park Tower in 2012 and sold it to Star Wars creator George Lucas and his wife Mellody Hobson in 2023 for $11. 2 million.

He paid $58. 75 million for four floors at 9 West Walton Street in 2017 and never finished the space.

Two of those floors went to Governor J. B. Pritzker for $19 million in late 2024. The other two sold this year for $15.9 million combined. His total losses on Chicago condos approach $30 million.

Citadel Shrinks From 1,300 to Hundreds

When Griffin announced the move to Miami in 2022, Citadel had about 1,300 employees in Chicago. That number has dropped to a few hundred.

The company still maintains a small office in the city, but it moved out of the tower that once bore its name. Griffin said asking employees to leave Chicago for Miami or New York was not hard.

The sad part, he added, was how many people who had built lives in Chicago were willing to walk away. Citadel now manages about $65 billion in assets and is one of the most successful hedge funds in history.

Boeing and Caterpillar Left Too

Griffin was not alone. Boeing announced in May 2022 that it would move its headquarters from Chicago to Arlington, Virginia.

Caterpillar followed a month later, relocating from the Chicago suburb of Deerfield to Irving, Texas. Tyson Foods closed its downtown Chicago office and consolidated in Arkansas.

TTX, a freight company, left for North Carolina. PEAK6 Investments moved to Austin.

McDonald’s CEO publicly warned that the departures were not good news for the city.

The Chicago Mercantile Exchange has threatened to leave if the city or state enacts what it called ill-conceived tax policies.

Chicago Faces $1.19 Billion Deficit

The city Griffin left behind is in deep financial trouble. Chicago’s 2026 budget deficit stands at $1.19 billion, the largest since the pandemic. City expenses have risen 64% over the past decade while revenues grew only 54%.

Federal relief money that kept things afloat has dried up. Mayor Brandon Johnson proposed a $16.6 billion budget that relies on new taxes, a record $1 billion surplus from special development funds, and $449 million in borrowing just to cover day-to-day operations.

Aldermen rejected his initial plan that included a $300 million property tax hike.

Credit Rating Sinks Toward Junk

S&P Global Ratings downgraded Chicago in January 2025 from BBB+ to BBB, just two notches above junk status.

In November, the agency revised its outlook to negative again, warning that another downgrade is likely if the city does not find structural solutions.

The downgrade matters because it makes borrowing more expensive.

Chicago has been on a borrowing binge for infrastructure, and the administration plans to put about $365 million on the city’s credit card next year to cover firefighter back pay and legal settlements tied to police misconduct.

Alderman Wants $1.25 Per Package

Alderman Gilbert Villegas introduced an ordinance to charge $1. 25 on every package delivered by ground transportation in Chicago.

He estimates the city receives between 110 million and 220 million packages per year, which could generate between $137. 5 million and $275 million annually.

Groceries, medicine, and food delivery apps would be exempt. The goal is to target retail shipments from Amazon, Walmart, and other online stores.

Villegas said residents who do not want to pay can shop at local brick-and-mortar stores instead. The mayor’s office says the tax would require state approval.

Head Tax Rejected by Council

Johnson also proposed a $21 per employee monthly tax on companies with 100 or more employees, which he called a way to make corporations pay their fair share.

The idea drew opposition from Governor Pritzker, aldermen, and business leaders. The Finance Committee refused to advance the spending plan in November.

A group of moderate and conservative aldermen are now working on an alternative that would double the city’s garbage fee to $20 per month and swap the head tax for the delivery fee.

Johnson has threatened to veto any budget that raises fees on working families.

Griffin Builds $2.5 Billion Miami Tower

While Chicago struggles, Griffin is building a monument in Miami. His planned 54-story headquarters tower at 1201 Brickell Bay Drive will cost about $2.5 billion and become Florida’s tallest building at 1,032 feet.

The project includes 1.3 million square feet of office space and a 212-room hotel on the upper floors. Construction was expected to begin in late 2025 but has been delayed.

Griffin has partnered with Related Companies to co-develop the project.

He has also spent more than $170 million assembling properties on Star Island for a personal compound.

Miami Leads the World in Wealth Growth

Griffin believes Miami could eventually overtake New York as a financial center.

A 2025 report found that both West Palm Beach and Miami surpassed New York City as the world’s fastest-growing wealth hubs.

West Palm Beach saw a 112% jump in millionaire residents over the past decade, while Miami saw a 94% increase. Florida’s population is projected to surpass 24 million by 2027.

Griffin, whose net worth now exceeds $50 billion, said South Florida offers oceanfront property, safe streets, great schools, and a strong sense of community.

New York, he joked, might someday be known as Brickell Bay North.

This article was created with AI assistance and human editing.

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