I didn’t really know anything about his life until this came up and I started looking him up. Grew up in Minnesota. Family migrated from Russia to America because of antisemitism in early 1900s.
Seems like he fell in ‘love at first sight’ with this girl whose parents were communists. HER parents were successful in breaking them up by sending the daughter away. She was pictured with him on an album. He must not have met their standard for a communist boyfriend.
I looked up the award you talked about because I like to gather as much info as I can before I condemn someone and I found the following link.
My word, I read the acceptance speech. Apparently they didn’t like it and he wrote some kind of apology. I don’t think he was a very good communist but see what you think after reading the speech and the apology. It wasn’t long after this that the mother orchestrated a break up. It almost looks like he was trying to impress a girl or something.
https://www.corliss-lamont.org/dylan.htm
Note that many of his early releases such as Talkin' John Birch Society Paranoid Blues (1963) leaned left. But you're probably right--if he was, indeed, a Communist at the time, he wasn't a very good one.