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I borrowed a friend's MacBook Pro, an older version running 10.15 and used a different USB cable and yes to my surprise that did work.

So I tried the known good USB cable with my MacBook Pro and...

Bumping this up hoping someone has an answer. I’d really like to use a teensey for a project but since I can’t even program Blink I’m at a loss what to try.

@defragster

Thanks for the suggestion. I did all the steps you mentioned.
Unfortunately neither board programmed normally. I did get the Verbose log files. Hopefully that can help.

I have a Teensy 3.2 and wanted to try it out for the first time. Got the code to blink the LED and made 2 changes in the delay values to make a distinctly different blink pattern. I plugged in the...