The city of Brentwood originally consisted of three land purchases by the families of Bompart, Gay and Marshall starting in 1804. The location on the Manchester Trail, traveled by mail coaches and prairie schooners heading west, became a prosperous little town. In the 1870s the town became known as Maddenville because of Thomas Madden who was a prominent business man in the community who owned several businesses, a rock quarry, tavern, barbershop, grocery and blacksmith shop. It was discovered in 1919 that the neighboring city of Maplewood was voting to annex their town.
To maintain autonomy the residents quickly decided to incorporate and on December 15, 1919 established the village of Brentwood.