"Jack Tarr the Sailor"

I listened to Ballad of Easy Rider yester-day (because it was Roger McGuinn's birthday), and I noticed a small ambiguity in "Jack Tarr the Sailor."  "Poor" in the line "'There goes Jack Tarr that poor sailor; he must go to sea once more'" could have the sense of "lacking money" (because as Jack himself says in the previous verse "me money was all gone") or the sense of "to be pitied" (because going to sea is something to be avoided; in the first verse, Jack says, "But a man must be blind to make up his mind to go to sea once more," and his advice in the last verse is "get married, lads, and have all night in, and go to sea no more").