The point that this rap (actually it's a talking blues) neatly sidesteps is that very likely he (and the rest of his family) had FBI files already. Seems like his dad, Woody, was a flat-out, redder-than-dawn-over-the-Kremlin, Communist, and was blacklisted as such. The Stockbridge police department had itchy trigger fingers for the Village Restaurant and Trinity Church ever since Alice and Ray had moved in (there being a few prep schools in the area...danger of minors getting hold of liquor, pot, and each other...) and they proposed to use the littering charge to harass them out of town.

Somehow I have a feeling that the draft board knew something about Arlo from the minute he shucked his drawers...