1 Correct, progressives should start cultivating (and funding!) a challenger now (or at least a rapid response super PAC, hint hint)

2 But it's a smidge more complicated than "someone like Bill Daley" https://twitter.com/MsKellyMHayes/status/1329578676690841606

Here's the deal: black Chicago decides the mayoral. They did in 2011, 15, and 19. To understand why, you need to look at 2011:

Rahm got the black vote
Brown got a handful of the black vote
Del Valle got a smidge of Latino/"white progressives"
Chico got the white racists

This is important because it put a hard number around the white racist vote in Chicago: 25%, or about 140K votes

It's also important because the "white progressive" vote is pretty marginal, something under 9% (more like <5%)

That 25% is what white candidates went for in 19

(Pause for full disclosure, I worked for Chico in 19, and shall not speak of it, just noting it and moving on)

The thing is, if there's a credible black candidate in Chicago, a white candidate is not going to get the black vote, period, do not pass go

The bar for "credible" is something I will not, as a white Chicagoan, comment on much, except that it's fairly intuitive

Thus, any white candidate facing a credible black candidate (such as, for better and worse, an incumbent), is going to start with that 25% of white racists. If they can't even get that 25%, they're not going to get to a runoff or be mayor, the end

You can call that 25% "blue collar," you can call them whatever, but white racists is what they are. They always think crime is skyrocketing, that black neighborhoods are war zones, black people are stealing city jobs, and property taxes mean welfare fraud. It's just fact

Now, the only thing a credible white candidate will talk about out of that list is that crime is skyrocketing. Which is why all the white candidates in 19 said exactly that, even though it was dropping, and police reform was much higher on voters minds than before (Foxx-Alvarez)

The problem is, that 25% isn't going to vote as a block. Any white can hum a few racist bars and come in and get a chunk of them, like McCarthy ranting about "illegal immigrants" or what have you. It's always going to fracture. You're not going to get to a runoff with it

That leaves the rest of white Chicago, call it, eh, 20% or so. Probably a bit less. You can call it the "north side" for shorthand. It's not, but close enough conceptually. North side:

Hates taxes
Likes parking
Pretty racist, esp about spending
But wants to feel not racist

See the problem? The north side isn't super thrilled with the same stuff white racists eat up. They like putting BLM signs in their yards/windows. They think Crime Is Up, but are squicked out by Blue Lives Matter ranting. They like buzzwords like "progressive"

For example the north side loves whining about TIFs, and will happily agree that "affordable housing" is A Problem and even think it means their own rent/mortgage (as opposed to racist whites who see it and think "black people")

So, now you have a problem:

There are more racist whites than north side whites

But the harder you work for racist whites, the fewer north sides you get

And also you should probably think about, like, the Latino vote, which is Complicated, and also infuriates racist whites

Any white candidate running against Lightfoot will see all of this in the polling. It's a rough path, and that's if the field is mostly cleared. Lightfoot, despite her missteps and bad press, will get a hefty bit of the black vote, and most of the north side

Which means you're probably looking at a Latino challenger, or a black challenger. But either will face a challenge of peeling off black seniors from Lori, and they're a real hard sell, and aren't super into police reform, and don't like taxes, and a bunch of other stuff

In summary:

A Bill Daley type is facing a much harder lift than you might expect, and there's not a lot of candidates capable of threading the racist needle

But progressives have an even harder lift with more variables, so yes start on that right now and also pay me money