The materials in this collection are primarily related to James B. Waller, lawyer and businessman from Frankfort, Kentucky and later Chicago; his wife Lucy Alexander Waller; their children, and extended families.

James B. Waller was born in Frankfort, Kentucky in 1817, to William S. Waller and Catherine Breckinridge Waller. He attended Center College in Danville, Kentucky, and Miami University in Oxford, Ohio, and received a law degree from Transylvania University in Lexington, Kentucky in 1838. He practiced law in Kentucky for the next 20 years, but also began investing in real estate after an 1849 visit to Chicago. Around 1860, Waller relocated permanently to Chicago and established a real estate business with his brothers William, Edward, and Henry.

James built a large home for his family on the north side of Chicago known as Buena House, and developed the surrounding area into the Buena Park neighborhood. After retiring from business in 1867, James B. Waller turned his attention to managing the large estate of his brother-in-law, Robert S. C. Aitchison Alexander, of which he was appointed administrator. James B. Waller married fellow Kentuckian Lucy Alexander in 1847, and the couple had 11 children: Mary Eliza (Minnie) Waller Osborne, Robert Alexander Waller, Catherine Breckinridge Waller Peet, Lucy Alexander Waller Young, James Breckinridge Waller, Susanna Lees Waller, Isabel Waller Knott, Adele Waller Rogers, Virginia Waller, and James Alexander Waller. Robert Alexander Waller attended Washington & Lee College, and later became a successful and respected Chicago businessman. The Wallers entertained often at Buena House, and the residence was known among Chicago's upper class for fine hospitality and lavish social events. James B. Waller died at his home in Chicago in 1887; Lucy Alexander Waller died in Chicago in 1902.

James B. Waller was the son of William S. Waller (1785-1855) and Catherine Breckinridge Waller (1788-1864), both from prominent Kentucky families. William S. Waller was clerk of the First Bank of Kentucky and later Cashier of the Bank of Kentucky for nearly 40 years. James B. was the fourth of William & Catherine Waller's 7 children; the others were Henry Waller, Anna Maria Waller, Catherine Waller Carson, William Waller, Edward Waller, and Susanna Preston Waller Lees.

Lucy Alexander was the daughter of Robert Alexander (1767-1841) and Eliza Weisiger Alexander (1796-1840). Robert Alexander, an immigrant from Scotland, served as a private secretary to Benjamin Franklin in France, and for many years was President of the Bank of Kentucky. In 1814 he married Eliza Richardson Weisiger, daughter of Daniel Weisiger, a prominent Frankfort resident. In addition to Lucy, Robert Alexander and Eliza Weisiger Alexander had three other children: Robert S.C. Aitchison Alexander (1819–1867), Alexander John (A.J.) Alexander (1828-1887), and Mary Bell Alexander Deeds. Robert S.C. Aitchison Alexander studied in England, earning a degree from Trinity University, and while there became the beneficiary of a wealthy uncle's Scottish estate. Alexander lived at the estate for nine years then returned to Kentucky, where he established the Woodburn Stud Farm on his family's property. Robert S.C. Aitchison Alexander built Woodburn Stud into one of the leading horse breeding operations in the United States, known for producing champion Thoroughbred and Standardbred race horses throughout the remainder of the 19th century. A.J. Alexander took over the business upon his brother's death in 1867.