S. D. Pitts was mentioned in the 17 June 1834 will of D. W. Pitts, proved 17 July 1837. “I give to R L Pitts, S D Pitts & Dandridge P Sale one thousand Dollars each.” [Essex County, Virginia, Will Book 24, pages 139–140.]

In about 1841, orators and oratrices Stephen D. Pitts and Anne his wife, who is a daughter of the late Major Thomas Pitts, Richard H. Pitts, and Fenelon Augustus Pitts complained that Major Thomas Pitts died in ____ testate. David P. Wright was named executor of the estate. The negroes were to be divided among all children to wit, Anne (wife of Stephen D. Pitts), Mary E. (wife of the said David P. Wright), Richard H. Pitts, and Fenelon Augustus Pitts (his grandson) as trustee for the benefit of himself and the other children of Davis Pitts, a son of Thomas Pitts. [Essex County, Virginia, Box Chancery No. 40, item 40-C-28.]

On 7 September 1842, Larkin Hundley complained to the Circuit Superior Court of Law and Chancery for Essex County that Stephen D. Pitts is in debt to him and is outside the commonwealth. That Reuben L. Pitts as executor of Thomas Pitts has in his possession property from the estate of Thomas Pitts in which Stephen D. Pitts has an interest in right of his wife Anne, daughter of Thomas Pitts. Filed as Hundley vs Pitts on 7 September 1842. [Essex County, Virginia, Box Chancery No. 51, item 51-I-20.]

On 7 September 1842, orator Augustine Owen of the County of Middlesex complained to the Circuit Superior Court of Law and Chancery for Essex County. That one Stephen D. Pitts is indebted to him $228.78 with interest from 1 January 1839. That Stephen D. Pitts has removed without the limits of the Commonwealth to the State of Louisiana. Reubin L. Pitts Esq. as agent and attorney for Stephen D. Pitts received from David P. Wright Esq. Executor of Thomas Pitts deceased late of Essex County two negro slaves allotted to Stephen D. Pitts in right of his wife Ann through the will of her father Thomas Pitts. One was called Nessee and was hired to Rix Jordan, and the other, Catharine, was hired to John C. Browne. Filed as Owen vs. Pitts. [Essex County, Virginia, Box Chancery No. 51, item 51-G-14.]

On 7 September 1842, orators William McDonald, Samuel McDonald and George M. Richardson merchants trading as Wiliam McDonald & Co. complained to the Circuit Superior Court of Law and Chancery for Essex County. That they trade wholesale in Baltimore in the State of Maryland. Stephen D. Pitts is indebted $1,690.16 with interest from 28 December 1839. He left the State of Virginia several years ago. Your orators are informed that Reubin L. Pitts Esq. agent and attorney has two negro slaves received of David P. Wright Esq., executor of Thomas Pitts late of Essex County, of which Stephen D. Pitts has an interest in right of his wife Ann, daughter of Thomas Pitts. That the negroes have been hired out. Filed as McDonald & Co vs. Pitts. [Essex County, Virginia, Box Chancery No. 51, item 51-H-6.]

On 4 January 1843, Reuben L. Pitts answered a bill exhibited against
him by Augustine Owen. He has in his possession two slaves, Catharine and Nessee, from the division of the estate of Thomas Pitts. They are the only property of Stephen D. Pitts in his hands. [Essex County, Virginia, Box Chancery No. 51, item 51-G-20.]

On 4 November 1842, David P. Wright executor of Thomas Pitts deceased answered a bill by William McDonald, Samuel McDonald and George W. Richardson merchants. He did deliver to R. L. Pitts attorney for Stephen D. Pitts the two slaves mentioned in the bill. Dated 4 November 1842. [Essex County, Virginia, Box Chancery No. 51, item 51-I-7.]

On 14 April 1843, William L. Ellis made a deposition in the Tavern of Thomas S. Muse in Tappahannock. That he has been living some years with Stephen D. Pitts’ brother, Reuben L. Pitts, and has often seen letters by Stephen D. Pitts and believes the example to be in his hand. [Essex County, Virginia, Box Chancery No. 51, item 51-I-5.]