The song is about a sailor who loses his leg in a bizarre rigging accident, and now he's shipping off to Boston to find his wooden leg. In a Songfacts interview with Matt Kelly of the Dropkick Murphys
, he explained how they attained the unpublished Woody Guthrie lyrics for this song and why they chose it. Said Kelly: "We were bestowed the honor by his daughter of being able to go through his lyrical archives and pick out a song or two of unpublished lyrics that we thought would be kind of cool. I mean, we had no business even being able to look at those lyrics - there have been some big names that have been after those lyrics for decades. I know Springsteen's been after 'em, and then Elvis Costello.
It's just so amazing that we were approached to look at them, never mind have the approval of the estate to use them. And the reason why we used that was because it said 'Boston' in it. (laughs) There's not a hell of a lot to the lyrics of that song, it's four lines of the verse, and then 'shipping up to Boston.' So it was pretty bare bones. And we'd had an instrumental that we started working on in Madrid, Spain in I think 2002. We recorded an older version of it, we just kind of did a demo of it, and it ended up on a Warped Tour sampler or something like that. And it sounds like a high school band, it's not very good. So we've been playing it live here and there, and so, like, what the heck, let's re-record this. The song grew a bit after recording it. And not many people knew it or had the recorded version, so I'm thinking what the heck, let's give it the real treatment and spend some time on it."