Yeah, the guy was decent and he cared a lot. Which is a good as a designer. It's also frustrating working with a UI dev who clearly wants to be a backend dev and don't give a shit that it wasn't to spec. I also really like my devs to push back on me because it helps improve the design. A lot of them have great feedback.

But, man, my old coworker really needed to learn to communicate and how to navigate and work with people. You can't attempt to go around your PM for every little thing.

OP said

The problems arise with middle managers who feel like I cut them off. They feel this way because I did, and usually do a better job. Why do I cut them off? Because voicing my concerns to them leads nowhere, so they basically force me to go around them.

Sure, if something is really terrible maybe go around someone for a specific part of a project. I put my foot down a few times on things that were REALLY terrible and were able to get it changed. But it almost seems like OP is doing it constantly. And sometimes, no matter how hard you fight for what you believe in, you lose. And you just have to do it. My old coworker would bring it up 3-4 times at least trying to change it even if everyone said no.