Roland Havilliard was the cousin of Dorian Havilliard.
Roland was a noted womanizer and was said to be more interested in women than in politics. This particular trait earned him Chaol Westfall's deep dislike, as Chaol's lover cheated on him with Roland. At his first meeting with Aelin, Roland's eyes wandered over Aelin in a way that made her feel filthy.
Upon first meeting him, Aelin noted that there was something she did not like about him, even though she could not say what.
Dorian did not enjoy his cousin's company.
According to Chaol, Roland was a "conniving wretch" and a "sniveling, spoiled ass".
Three years prior to Crown of Midnight, Chaol punched Roland in the face with enough force to render him unconscious. This ostensibly resulted from Lithaen, Chaol's lover, cheating on him with Roland.
Roland traveled from Meah to Rifthold to serve in the royal council. Much to Dorian's chagrin, he was ordered to entertain Roland. While touring the gardens, they encountered Chaol and Aelin, who were finishing their morning run. Chaol greeted Roland stiffly, and Roland acknowledged him. Dorian then introduced Aelin as Lillian, saying that she worked for the King of Adarlan. Roland commented that she must be new to the court, as he had not seen her before; he then inquired about the type of work she does. Chaol demanded to know why Roland was there, to which Roland replied that the King offered him a position on the council. He eyed Aelin lustily and expressed interest in "working together sometime".
As he and Roland wandered the castle, Dorian pondered why his father offered the council position to Roland, as Meah, though prosperous, was not particularly politically important, and Roland was inexperienced and more interested in girls than politics. When he solicited further information on "Lillian", Dorian answered that her story was hers to tell. Roland ignored him and asked whether Lillian's services were available to other councilmen. Dorian informed him that Lillian's contract was solely with the King. He tried to tell himself that Roland was harmless, but he questioned that statement.
In Queen of Shadows, Roland appeared once more, but this time he was in Morath and had a collar on him. He was possessed by a Valg prince. In the end, he begged Manon Blackbeak to kill him, and she did.