Ken Griffin has officially closed the book on Chicago.
After more than 30 years, the Citadel founder — once the state’s single largest taxpayer — is now fully divested from Chicago real estate. His final property went under contract on December 3, 2025, marking the billionaire’s complete retreat from a city he now portrays as unsafe, overtaxed, and mismanaged into decline.

What began as a corporate relocation in 2022 has evolved into a total personal departure, punctuated by steep real-estate losses and increasingly sharp public criticism of Illinois leadership.

Below is the definitive timeline of Griffin’s Chicago disinvestment and the political fallout surrounding it.

Key Events in Griffin’s Departure

🔹 2022 — Citadel HQ Leaves Chicago for Miami

Griffin stunned the financial world by moving Citadel’s global headquarters from downtown Chicago to Miami.
His explanation:

rising violent crime

“woke” governance

dysfunctional state politics

He said employees were “begging” for the move.

🔹 April 2024 — Griffin Begins Selling High-End Chicago Holdings

He sold two penthouses at 9 West Walton for $15.9 million, far below the roughly $59 million he’d invested in the building in 2017.

A spokesperson blamed “years of failed leadership in Illinois.”

🔹 Late 2024 — More Sales, More Losses

Griffin unloaded a Waldorf Astoria unit for $10.2 million, about $3 million below what he paid.
A month later, he accepted $19 million for the top two floors of his signature 9 West Walton penthouse — a staggering 44% loss on the $34 million he paid in 2017.

The penthouse included:

an unfinished pool

two massive terraces

bespoke luxury interiors that never made it to completion

Griffin called the price collapse “a small portion of the bill for failed political leadership.”

🔹 October 2025 — Griffin Goes Public Again

Speaking at Citadel’s Future of Global Markets summit in New York, Griffin said Chicago had become a city defined by:

“crime, cronyism, and failed policies.”

He revealed Citadel’s Chicago headcount had collapsed from 1,300 employees to a few hundred, calling it “a real-time case study in what bad governance does.”

🔹 November 2025 — The “Bullet Holes” Interview

In a Fox News interview, Griffin claimed:

there were 25 bullet holes in the exterior of one of his Chicago properties

several Citadel employees had been victims of drive-by shootings

Chicago had become a “failed city-state awash in violent crime”

He contrasted Chicago dinner conversations (“crime, decline, dysfunction”) with Miami dinners (“kids, futures, optimism”).

🔹 December 3, 2025 — The Final Property Is Under Contract

Griffin’s last remaining Chicago asset — a 9 West Walton penthouse — finally went under contract after multiple price cuts.

At this point, the billionaire has zero real estate left in Chicago.

The Financial Picture: Losses, Yet Strategically Irrelevant

Griffin’s sales across Chicago have generated tens of millions in losses — by some estimates $40+ million on paper.
But that’s minimal relative to his:

$42 billion net worth (2025 estimate)

$84 million Hamptons estate

$122 million London mansion

expanding Miami and Palm Beach portfolio

His team frames the losses as symbolic, not financial — a message to Illinois politicians.

Why He Says He Left Chicago

1. Crime

Griffin alleges personal and employee danger:

bullet-damaged buildings

violent incidents near offices

carjackings and assaults in the Gold Coast

2. Taxes

Illinois’ tax climate is “punitive,” he says.
He redomiciled to Florida’s no-income-tax system.

3. “Woke” Governance

Targets include:

Gov. J.B. Pritzker

Chicago Mayor Brandon Johnson

progressive city policies he says “chased out prosperity”

He’s called Chicago an example of “what happens when ideology overwhelms competence.”

Larger Trend: Chicago’s Wealth Exodus

Griffin’s departure symbolizes an accelerating pattern:

luxury real estate selling at 10–40% losses

high-net-worth residents relocating to Florida or Texas

major employers (Citadel, Boeing, Caterpillar, Tyson Foods) shifting operations out of Illinois

Griffin’s taxes once accounted for 1% of Illinois’ entire revenue, per state documents cited in 2024. His exit leaves a notable fiscal hole.

Bottom Line

Ken Griffin’s sell-off wasn’t a sudden break — it was the final chapter of a three-year exit strategy.
Chicago lost a billionaire, a household-name employer, and a symbolic investor in its luxury real-estate renaissance.

Whether viewed as:

a warning about governance,

a billionaire tantrum, or

a failure of local leadership,

Griffin’s full withdrawal carries real economic implications for a city already struggling with crime, tax flight, and a shrinking business base.