The Monitor is based loosely on the American Civil War and it features guest appearances by various friends of frontman Patrick Stickles portraying various historical figures in spoken word parts. They include Vivian Girls guitarist Cassie Ramone and Hold Steady frontman Craig Finn, who play Jefferson Davis and Walt Whitman respectively. Davis was the president of the Confederate States of America and Ramone, who is an old high school friend of the Titus Andronicus singer opens this song with a line from Davis' February 4, 1861 speech to the newly-seceded Southern states: "Upon my weary heart was showered smiles, plaudits and flowers, but beyond them I saw troubles and thorns innumerable."
Stickles explained to Spinner UK the casting of the female guitarist was linked to the scorn her group has drawn from bloggers who originally championed The Vivian Girls. He said: "That Jefferson Davis quote, I really thought about her when I heard it, because that song is kind of about being an indie rocker and putting yourself out there and how pretty much trying to express yourself in modern times is tantamount to putting yourself on the chopping block." Stickles added: "The Vivian Girls got way more than their fair share of that, people on blogs who don't have anything better to do than pissing on them for no reason at all, trying to feel better about their own worthless lives. I was thinking about how being an indie rocker, maybe there are moments you can be celebrated and put on a pedestal, but it's safe to guess that if that happens, you're also going to get the flipside of that. People are going to be looking to knock you off your high horse."
Stickles told Spin Magazine that The Monitor conflates the bloody battles of the Civil War with, "the failure to make love work in the emergency of modern life." His original inspiration was the Ken Burns documentary The Civil War, which he watched after moving away from New Jersey to Boston. He recalled: "[My ex-girlfriend] went to bed at a normal hour. I'd stay up late watching that movie and thinking about New Jersey. Then she gave me the boot, and I shat all these feelings out - and it became our record."