Arborist damaged tree. Now what?

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Step one is to diagnose the issue and correct the problem. Once the issue is diagnosed, then any blame can be assessed. Quite frankly, the OP seems more concerned with suing the original arborist than figuring out what is going on with his tree.
Sheesh. I've never sued anyone in my life. But we live in a litigious culture so I understand why you started there. I'd say I'm coming from a place of significant upset, sure. I asked about insurance not because I want to sue someone but because I want to make sure the company helps resolve things. But to all your points, I'll verify with a third party what's going on
 
That patio is raised above street level, looks like about 4'-5' so, essentially the tree is in a container, assuming there's a footer and foundation for that raised patio.
It's probably rootbound... among other things

I agree with ATH about the cause and effect. The decline in the crown is unrelated to the pruning. You need to be looking at the soil, what has been used on the patio under the tree? How friendly is that neighbor, and what do they think of your tree?
Super friendly neighbor. Not sure on the patio comment. It's concrete pavers with sand between them. We don't use any harsh cleaners, etc.
 
That patio is raised above street level, looks like about 4'-5' so, essentially the tree is in a container, assuming there's a footer and foundation for that raised patio.
It's probably rootbound... among other things
There's no foundation below. We live on a sloping street. Nothing but dirt below the patio.
 
About insurance:

There are two types of liability insurance for businesses or professionals: general liability insurance and "E&O" (errors and omissions) insurance. If your arborist caused damage to you or your property by botching the job, that falls under E&O insurance, which the arborist might or might not have. If instead you tripped over his equipment and broke your ankle, that would come under general liability.

Ultimately you can't claim against his insurance, you have to send him your complaint and request for compensation, and ultimately sue him if you can't otherwise get satisfaction. His insurance isn't really your business, though it's nice to know if there is enough money available (either his own assets or insurance) to pay if you win in court.

Since you are not qualified to identify the cause of your tree's problems, you won't be able to prove anything unless you get a consultation from a good forensic arborist, so that's the obvious first step in figuring out both who/what is to blame and how/whether the tree can be saved.

If the tree was ailing before your arborist arrived, and he was an actual arborist rather than just a tree surgeon, he should have told you about your tree's problems before agreeing to do work on the tree. Or at least mentioned it while he was doing the work, if that was when he noticed it. Did he mention anything? If not, Raintree might be onto something. There are sneaky ways to kill a tree if someone wants to. Copper nail(s) driven into the trunk near the base, for one.
They are a legit arborist. They didn't mention any sickness and specifically said the only reason to trim it was the neighbor's roof and any aesthetic preference we had. We agreed to keep it relatively full, shape it a little, etc. I'm not concerned with the neighbors. We're on great terms.
 
Getting a bit off-topic, do I see power lines running through the tree's canopy? Is that just the feeder line to your house, or a line going through from pole to pole?

If the latter, you might want to say goodbye to this tree anyway since the power company might come and butcher it someday if they think it's a danger to their lines.
It's supply to the homes further down our block. At this point the lines have plenty of space. And this is an incredibly common tree across the city sidewalks so I'm sure they're familiar with how it grows, etc. Not worried there
 

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