David A. Sayre came to Lexington in 1811 as an apprenticed silversmith and during the next several years prospered enough to branch into private banking in 1823. In 1828, he purchased a building at the corner of Mill and Short Street, locating his banking offices on the ground floor and his family on the second floor. The firm of D. A. Sayre Company continued to operate from this location until its liquidation in 1899.
In 1829, Mr. Sayre purchased the residuary interest in the first Bank of Kentucky (which see). In the 1850s, he purchased the adjoining property and built a stately residence there. His bank and residence was subsequently demolished to make room for the new Security Trust Building.
In the firm's backroom, the leading citizens of Lexington met daily to discuss the important subjects of the day, ranging from business ventures, the Civil War, thoroughbred horses to their favorite brand of bourbon. In this room, the founders of the Agricultural Society of Fayette County (the University of Kentucky) first met to organize an institution of higher learning. The Lexington Cemetery was also organized from this backroom, with the Cemetery's Board of Directors holding informal meetings there. This backroom was also the site where various turnpike companies were organized (that built the highways throughout Central Kentucky), as well as the Lexington & Ohio, Lexington & Frankfort and Frankfort & Louisville Railway Companies.
After Mr. Sayre's death in 1870, the firm's operations were continued by his nephew, Ephraim D. Sayre. Ephraim Sayre was one of the founders in 1886, and eventually, President of the Security Trust and Safety Vault Company. By his death in 1899, Mr. Sayre consolidated most of his private banking operations with the Security Trust. The remaining assets of the D. A. Sayre & Company were liquidated by Security Trust as executors of the estate of Mr. Sayre.