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Not sure why this is about Chicago. Almost all of the major hedge funds and banks have been increasing their Miami presence over the past 18 months. Maybe it really is because of the violence, but I think he is making a political play and taking advantage of Florida’s tax breaks over anything else.
He also tried to push a candidate for election (Richard Irvin) that people didn't like. The instances of crime probably didn't help, but the day to day of being in Chicago is vastly different from the rhetoric that he and the news use to describe it.

Overall I am not sure how this will affect the city (net good or net bad)... be interesting to see how it plays out.

Net bad. Less reputable companies and more crime leads to city rot.
How about the headline about colleagues getting mugged? Inability to get hires to relocate to Chicago?
Colleague is an ambiguous term. I wonder if he meant Citadel employees (only a couple thousand, which is pretty bad, if true)? The CEO of Citadel has tens of thousands of 'colleagues', though.
The only thing I hear about Citadel is that it's a sweat shop of quants. Is it really a relocation problem or a reputational issue.
> tax breaks

A completely legitimate reason for moving. If they have problems because the low taxes can’t pay for the services they want, they can move back. Of course this is laughable because the simple observation here is that the tax dollars do not fix these problems, and seem to make them worse.

Miami's fresh water supply comes from an area that is likely to be inundated by sea water. The city itself is likely to be constantly flooded in the near future.

This seems like a short term bet.

I suppose it's a complicated feedback loop of companies following talent and talent following companies, but Miami has been popular with fintech bros, whereas chicago doesn't have the same pull for a lot of reasons, not least of which are taxes, weather, and yes, crime.