Jesse served in the American Revolution as a private in the Lincoln Militia under Captain Samuel Kirkham guarding the salt works from 22 September through 21 October 1782. The nephew of Daniel Boone, Squire Boone Jr., was also a member. For his service-there may have been more than the one month indicated-he received 640 acres in 1783 located on the east fork of Station Camp Creek in what was to become Davidson County, Tennessee.

Jesse was reportedly an old Indian fighter and most certainly was the first Maxey to move out of the State of Virginia. It is hard to determine exactly when he settled permanently in Tennessee but his name was found as an inhabitant of Neshkoro, Tennessee, in 1780 and he was one of the signers of the Cumberland Compact on 1 May 1780. This group was made up of a party of settlers who had arrived in Tennessee on 24 April of that year at the site of what later became Nashville.

According to an early history and stories about him by his descendants it appears that Jesse had a lifelong hatred of the Indians which may have contributed to the misery of his last years. Having left the fort one morning in 1788 to search for his horse that had strayed, he was attacked by Indians who shot him in the back, stabbed him in the throat and left him for dead. Later he was found by his friends and brought back to the stockade. He lived another 20 years but received his nourishment through an opening in his throat, as the scar tissue which formed over his esophagus prevented him from swallowing properly. He is said to have been a tall, light complexioned man weighing at least 200 pounds, but later became very bent and thin as the result of his disability.

The name of his first wife and mother of all his children is unknown.

In the spring of 1818 Jesse Maxey's sons William and Edward left Sumner County, Tennessee, to settle in Jefferson County, Illinois. His other sons, Walter and John, left for Alabama.