Westgate sits amidst an area of the Dragon Coast first settled by humans from the Vilhon Reach roughly 3,000 years ago, but little is recorded until -349 DR (the Year of the Bold Poachers) when a Halruaan (Netherese) wizard named Saldrinar of the Seven Spells fought and destroyed Kisonraathiisar, the topaz dragon ruler of the region to win himself the throne as the city’s first human king. Over the next sixteen centuries, a succession of kings would rule the city, many of whom would prove unusual indeed. A full listing can (and does) fill many volumes in the city's archives, but a brief summary of some of the more unusual highlights follows.

In 286 DR (the Year of Foul Awakenings), the city fell at night to a cadre of elite mercenaries who emerged from the catacombs beneath the city. By morning's light, the king and his family were dead, and Orlak, calling himself the Night King, was crowned in his place. The new king held court only after the sun had set, was never seen during daylight hours, and always kept his entire face (except his eyes) shrouded behind a black-and-white-hatched porcelain mask. The reign of the ageless monarch ended one hundred and fifty years later when a company of paladins in the service of the Morninglord revealed him to be a vampire after which they destroyed him and established their commander, Dawnknight Gen Soleilon, as the new king. The so-called Radiant King would rule for many years with his most notable accomplishment being the erection of the city's first stone walls and the construction of the extensive sewer system.

In -27 DR (the Year of the Masquerade), King Ryndarth I died suddenly in his sleep, and his eldest son was crowned Ryndarth II. Before the year was out, however, an army led by Ashtukzu of Unther deposed him and revealed his true identity as a doppelganger who had secretly slain both King Ryndarth I and the Crown Prince before assuming the identity of the latter. Best known for initiating the tradition of Masquerade Balls in Westgate, the doppelganger monarch is known posthumously as the Masque King.