It's baffling to me how everyone seems to hate the guy and say he was a terrible leader, employee, and person, and yet companies seemed to have been valuing him like a diamond. How did that work? Is he just good at duping and persuading and sweet-talking people? Does he have some past accomplishments that were respectable? Does he have some insight into autonomous driving no one else has? Why would Google and Uber bet so much on this guy?

He was on the Berkeley team for the original DARPA Grand Challenge. Their team was notable for being a motorcycle while everyone else used a car, the complexity of using a motorcycle earned them big points with the higher-ups even though the bike didn't do very well on the course.

So if you were a CEO looking to hire a senior guy for autonomous vehicles, he was one of the most senior in years of experience, pretty much nobody was working on autonomous vehicles prior to the Grand Challenge.

Sure, but once it becomes clear that he doesn't fit in the culture and causes more issues than he solves, why does he keep getting promoted and his pay increased?

I suggest that wasn't as clear as you think it was to the right people (either through incompetence, ignorance, or bad leadership), or that if they did have some idea that he wasn't a great fit they were hoping that he would produce a miracle that would make all the pain worth it.

Coming in with wunderkind status gives you a lot of leeway with some people, and things need to be pretty bad before the people that hired you will admit that they made a mistake, hired the wrong person, and paid them way too much. Admitting such a mistake does some damage to your ego and reputation of hiring problem solvers. Plus, by many accounts he was producing decent results- after all, he's led some pretty famous projects, and most of the projects weren't regarded as failures, so why should he be regarded as a failure? Other than stealing IP and being a dick, he's not usually called a loser or a failure.

Because "results" matter more than culture. Just watch a TV series "Succession" to see how the upper echelons of people treat/think about ordinary engineers and senior engineer.

The decision makers who hire people like this and decide their compensation aren’t dealing with the environment day-to-day.

Never underestimate the damage an absentee boss with no skin in the game can cause to the boots on the ground. Out of sight, out of mind is all too real.

He was incredibly skilled at "managing up" - which in this case meant telling Larry and Travis what they wanted to hear.

According to the book Autonomy, he was a pioneer in the field of self-driving car, and excelled at making things happen. That said, he was always controversial and ethically dubious even when he was in Google. As the org that he was in grew larger. And he certainly failed in large enough orgs, such as Uber.

Because the world is only a meritocracy in the sense that the inventor of the term was trying to mock.