Perhaps Uncle Monk had heard of Slave Dick's exploits before expressing his own heroic nature in 1782.
If Dick Pointer's exploits were carried into the Kentucky District of Virginia, the message conveyed was that slaves could demonstrate courage, not that valor brought freedom.
Deed Book 1, pages 400-401 Greenbrier Co. VA March 1801 [Spelling and capitalization are as found in original document.]
"Know all Men by these presents That I James Rodgers of the County of Greenbrier & State of Virginia Do agree to Immancipate & Set free My Negroe Man Named Dick pointer on the Conditions hereafter attentioned havit that if the said Negroe Dick Doth Well Truly behave himself in all things so that I Never Come to Trouble on his Account then this Immancipation to be finel but if he Should fail in any of the above obligations so that I May Sustain any injury Thereby he Shall from That instant Return To his Usual Slavery & forfit Every part of the Restitution he has given to Obtain it at present-after A True performance of the above I bind MySelf My heirs etc firmly by these presents Sealed With my Seal & Dated this 2th Day of March 1801.
James Rodgers" [SOURCE]
Freedom had its drawbacks as well.
In grateful thanks, the settlers wrote to VA asking the State to give Dick Pointer his freedom, but this did not happen as a result of their request. Dick Pointer and his family were later sold by Col. Donnally to the See family. Pointer was eventually freed by a Mr. Rogers, only to die in poverty because, as they became old and infirm, Pointer and his wife could not sustain themselves on the small farm which neighbors provided them. [SOURCE]
It is probable that James Berry (c1752-1822), whom Monk carried to safety, had a pre-existing relationship with Greenbrier (then in Virginia, now in West Virginia). Berry had there enlisted with Revolutionary forces one year prior to the attack on Fort Donnally.
An interesting footnote is that history suggests that Dick Pointer's son was captured 'while young' by native warriors. For his able services as a translator, Wyandot elders granted Johnathan Pointer his freedom. Johnathan continued to reside among native peoples for many years, working with a Methodist preacher to convert them to Christianity.