“Ain’t nothin’s sure,” said Chester, still watching out his doorway. “‘Cept trippin’ and fallin’ into the garbage pile. That gag always works.”
First appearance: WB2014 Dylan and Thomas - Part 2
Chester is fat with a hairy back, a literal gossip monger, and more or less the man who keeps order behind the scenes in court. "As the courtiers and city officials and warlords formed their secret cadres and plots, Chester kept abreast of it all. He sewed confusion and distrust among allies, cultivated counter-plots, and punctured those who got too powerful for Opencola’s good. All with the power of bad jokes." WB2014 Dylan and Thomas - Part 2
Rhyme-o-mancer Dylan Fugue describes him as his "one friend." Chester refers to Dylan as "chumpus" and "chumpy". He forms a duo with Dylan, who intuits the intentions of courtiers, and Chester helps or hinders the courtiers in accordance with his duty to the side. He seems intent on helping Dylan with his task of composing an Epic Poem in honor of the side's Chief Warlord.