Chicago loses third CFO this year as $882 million gap looms

Another exit in the finance seat

Ashlee Gabrysch, appointed in August by Mayor Brandon Johnson, resigned after a brief tenure as chief financial officer. In her statement, she said she had "faithfully discharged" her fiduciary duty but concluded staying on would compromise her integrity and professional obligations, so she resigned. Two earlier CFOs in 2026, Steven Mahr and Jill Jaworski, had already departed this year.

Michael Belsky, the city's comptroller, was tapped to step in as acting CFO effective immediately, according to a mayoral spokesperson. The shake-up compounds City Hall volatility while the first-term mayor both readies his next budget and seeks reelection.

Allegations and a coming review

Johnson's spokesperson said Gabrysch was largely absent during key stages of budget work and that she instructed the city treasurer to make a $75 million payment without the legal authority or required processes. The spokesperson noted that they tried several times to speak with her about the move, but it "went unresolved," and the case will be forwarded to the Office of Inspector General for an independent review.

Alderman Bill Conway, the city council finance committee's vice chair, urged a swift and thorough probe. He warned that the timing, with a budget deadline approaching, could affect confidence in the city's financial statements and, by extension, its credit standing.

When financial leadership shifts, investors benefit from learning new tools to stay informed. We're hosting our first ever investor livestream on 11/17 to show you how to use ChatGPT and Claude to invest like a pro, hosted by Briefs Finance CEO Jaspreet Singh. Save your seat.

Ratings, debt load and a delayed deal

After weighing a third-quarter sale, Chicago now plans a January general obligation bond deal that could reach $700 million, saying it preferred to wait for clarity on the budget. By Dec. 31, the budget must be approved. The city reported in March that long term general obligation bonds outstanding exceed $5.8 billion.

Ratings remain a pressure point. Fitch lowered the city's general obligation rating to BBB+ in February, which is three steps above speculative grade. S&P Global Ratings assigns a BBB, two steps above junk. For context, New York City's general obligation debt is rated AA by both Fitch and S&P, while Los Angeles carries AAA from Fitch and AA- from S&P, according to BondLink Inc. Lower standing than New York has contributed to higher borrowing costs for Chicago.

What investors should watch

Belle Haven's Ryan Ciavarelli said markets were already braced for a tough budget season and that some of that caution is reflected in prices. He added that rating firms will zero in on how the deficit gets addressed using recurring measures versus one time moves, and that the quick loss of another CFO raises downgrade risk.

The bottom line: fresh leadership upheaval, an $882 million shortfall, an alleged $75 million payment under scrutiny, and a bond sale pushed to January all keep credit under the microscope. Track the budget outcome and any findings from the inspector general as signals for Chicago exposure in muni allocations.

Using smarter tools can help long term investors find clarity amid uncertainty. On 11/17, our CEO Jaspreet Singh goes live for our first ever investor livestream on how to use ChatGPT and Claude to invest like a pro. Register to join him.