- Born: 22 May 1758, Hillsborough, NC
- Marriage (1): Mary Pennington on 6 Jan 1785 in Wilkesboro, NC
- Marriage (2): Polly Green about 1776
- Died: 10 Mar 1841, Breathitt County, Quicksand Creek, KY at age 82
Jesse Bolling was in the battle of the Cowpens during the Revolution. He came to Ky. in 1810 and settled in Clay Co. on the Middle Fork of the Ky. River. That section of Clay Co. later became Perry Co. and then Leslie Co. Jesse enlisted in the Revolutionary war in 1780 in Wilkes Co. NC. He marched to Salisbury and was employed in guarding British and Tory prisoners. He marched with the prisoners from the Salisbury line to VA with the British in pursuit.
He served three months and was discharged. In the spring of 1781 he reenlisted in Wilkes Co. NC and marched from there down the Yadkin River to the trading ford and was used in guarding against an invasion by the British. In July or August, 1781, he again reenlised in Grayson Co. Va. as a light horse soldier and marched to NC to a place where the troops guarded a town against the British.
After the war Jesse and his brother Benjamin Jr. settled in Flat Gap in Wise Co. Va. (Wise Co. was formed in 1856 from parts of Lee, Russell, and Scott Co.Va.) where Jesse became a Baptist minister.
He was pastor of the Old Stony Creek Church at Fort Blackmore, Va.(This is in Scott Co.) around 1800. He married Mary Pennington of Lee Co. Va., his second wife.
The following is taken from the "Dr. John J. Dickey Diary" recorded in the 1870's and beyond:
"My great grandfather, Jesse Boiling, came to KY in 1810. My grandfather, Elijah Boiling was born at the Three Forks of Powell River in Lee Co., Va. in 1798, and when he was 12 years old his father removed to Perry Co., Ky. Daniel Duff baptized my grandfather Elijah Boiling. Rev. Andrew Baker baptized my great grandfather at Blackwater Church, now Hawkins Co., Tenn.".
The "Elder" in Jesse's name comes from the title given him by the Church. It was their belief that no mortal man should be addressed as Rev., therefore his title was Elder Jesse, not Rev. Jesse.
Jesse Boiling (their spelling) appeared on the rolls of the "Early Settlers of Wise Co." , a history of Wise Co. Others were Alexander, Amos, Delaney, Ezekiel, Hosea, Jeremiah, and John D.
Jesse married Mary Pennington, daughter of Micajar Pennington and Nancy Jones, on 6 Jan 1785 in Wilkesboro, NC. (Mary Pennington was born on 6 Jan 1785 in Wilksboro, NC and died on 21 Mar 1843 in Breathitt County, Quicksand Creek, KY.)
Jesse next married Polly Green about 1776. (Polly Green was born in 1760 and died in 1780.)