Chicago’s $10 Billion Gamble: Politics, Pensions, and the Portfolio Manager Who Won’t Buy Treasuries

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The City of Chicago is staring down a $1.15 billion deficit, $53 billion in pension debt, and a credit downgrade—yet its treasurer, Melissa Conyers-Irvin, is making headlines for boycotting U.S. Treasury purchases to protest Donald Trump’s immigration policies. Overseeing a $10 billion investment portfolio with a 3.6% annual return, Conyers-Irvin’s move raises eyebrows as she pushes into a Congressional run while critics question her financial acumen, past ethics investigations, and unconventional résumé. Meanwhile, Mayor Brandon Johnson floats new taxes, high-interest borrowing schemes are shot down, and Standard & Poor’s is sounding alarms. This segment dives into the political theatrics, the staggering fiscal reality, and the leadership choices steering one of America’s biggest cities into deeper uncertainty.

Episode Transcript

Speaker 1 (00:00):
The Watchdog on Wall Street podcast explaining the news coming
out of the complex worlds of finance, economics, and politics
and the impact it we'll have on everyday Americans. Author,
investment banker, consumer advocate, analyst, and trader Chris Markowski.

Speaker 2 (00:16):
Who wants to manage ten billion dollars. Ten billion dollars,
that is the that's the investment portfolio for the city
of Chicago. Now, the treasurer of the City of Chicago.
This Melissa con Years slash Irvin. She she came out

(00:39):
and said that she is not going to buy any
more treasure going to boycomp the purchase of US Treasury
debt to protest Donald Trump's immigration corrackdown there, I'm gonna
have money given to Trump because he's pepper spraying people.
And she's going off on this uh rant here first

(01:03):
and foremost. If she doesn't buy treasuries, uh, somebody else will.
It's as simple as that, not to mention the fact
you kind of almost have to if you're running a
fund like that, when you have to have for all
intense purposes risk free investments because you have to make

(01:24):
constant payouts. Hmm. Let's take a look. Let's take a
look at Chicago. The city is facing a budget deficit
of one point five billion for the coming year, has
fifty three billion dollars in pension debt. Now again, the
city of Chicago is basically dumb and dumber. Over there,

(01:44):
you've got the mayor, Brandon Johnson. You've got this Melissa
con Years Irvin and many many more. You got Pritzker
there as well. He's hanging out the governor in the background,
the Chicago Mayor, Brandon Johnson. He was thinking about taken
out a high interest loan to cover pension payments, and

(02:05):
I got mixed by the school district. He's now looking
We talked about this. He wants to put a head
tax businesses that hire people that are going to charge
you per employee. Now not making this up. A yacht
tax and an uber tax. There are some of the
other things he's throwing out there. Standard Poors is already
downgraded Chicago's debt because of all sorts of structural imbalances there.

(02:32):
CHICAI actually that their fund right now doesn't own any treasuries,
but it's owned two hundred million over the past three years.
So I was curious to see this genius. Melissa Kanye's Irvin,
I want to take a look at her performance. The
city's portfolio had a three point six percent return last year.

(02:56):
I can get my checking for kriideut a three point
six percent returned. That was what she produced. Ten year
treasury has a higher yield than that. Oh but you know,
I know she had to make news because I guess
she's running for congress now in the seventh congressional district.
I do little homework. I wanted to take a look

(03:16):
at this genius Melissa con Years Irvin. Yeah, she was
previously a Democratic member of the Illinois House of Representatives.
Prior to that, she worked in the insurance industry at
both All State and CS Insurance Strategies. Twenty twenty three,

(03:41):
she faced an ethics investigation into allegations surrounding abuse of power.
Former employees alleged her work of requiring staff to perform
personal tasks, including planning birthday parties, grocery shopping, and also
forcing BMO Harris Bank to provide a mortgage for her husband,

(04:02):
Chicago Alderman Jason Irvin, it's right, take you. You know
what else is that Jasmine Crockett does the same thing.
So I even look further, I did a little more homework.
Why not decide to go down that rabbit hole this morning?
What did she do at all? State, a claims adjuster,

(04:23):
human resources, and a freaking community organizer. You can't make
this up. She's managing a ten billion dollars portfolio for
the city of Chicago and this is her resume. Watchdog
on Wall Street dot Com