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WEBMISTRESS speculates:
Lindsey's guitar is highlighted in this song. It sounds very nice. As for the words themselves, you can see by the cover of the album who they're about. John Stewart was very active in Kennedy's campaign and, of course, was distraught when he was assassinated. His disillusionment in the wake of that event is evident in the song.
There are references to the Vietnam War also, which he obviously didn't support. It is also interesting to contrast this song and the earlier, similarly titled Heart of the Dream off of Bombs Away Dream Babies. The similarity in titles calls attentions to the very different attitudes of each song. Heart of the Dream revels in the promise of America - he even refers to America as "the promised land" in that song. Then you have this song, which is full of despair at the state of the country. Personally, I find the song very affecting, and I wasn't even alive at the time Kennedy died.