Roland Havilliard was the cousin of Dorian Havilliard.
Three years prior to the 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, who later took Lithaen back to Meah with him.
Roland travels from Meah to Rifthold to serve in the royal council. Much to Dorian's chagrin, he is ordered to entertain Roland. While touring the gardens, they encounter Chaol and Celaena, who are finishing their morning run. Chaol greets Roland stiffly, and Roland acknowledges him. Dorian then introduces Celaena as Lillian, saying that she works for the King of Adarlan. Roland comments that she must be new to the court, as he has not seen her before; he then inquires about the type of work she does. Chaol demands to know why Roland is there, to which Roland replies that the King offered him a position on the council. He eyes Celaena lustily and expresses interest in "working together sometime".
As he and Roland wander the castle, Dorian ponders why his father offered the council position to Roland, as Meah, though prosperous, is not particularly politically important, and Roland is inexperienced and more interested in girls than politics. When he solicits further information on "Lillian", Dorian answers that her story is hers to tell. Roland ignores him and asks whether Lillian's services are available to other councilmen. Dorian informs him that Lillian's contract is solely with the King. He tries to tell himself that Roland is harmless, but he questions that statement.
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 Celaena, Roland's eyes wandered over her in a way that made her feel filthy.
Upon first meeting him, Celaena 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".
Roland had blond hair and blue eyes. Aelin remarked that he looked similar to Dorian.
- Crown of Midnight (first appearance)
- Heir of Fire (mentioned only)
- Queen of Shadows
- Empire of Storms (mentioned only)