Lyric discussion by pmoney 

Cover art for Bermuda Highway lyrics by My Morning Jacket

I think "Sometimes I wonder why that meek guy got all the fame Maybe I'm to blame for his short, bitter, fucked-up life"

is referring to one of his "dreams" that he didn't follow through with or pay attention to. He is responsible for the "short fucked up life" because he disregarded it instead of keeping track of his "silly dreams."