The majority of Kentucky's settlers were either Revolutionary War soldiers themselves or the sons of Revolutionary soldiers. The United States Congress eventually passed laws providing pensions for service in the War for Independence and many of these contain detailed accounts of the soldier's service. With a monthly income at stake, not all applicants were honest in their statements of service. The truth of James and Thomas Howard's service was later called into question but the details of service they provided in their applications, whether or not they were actually there, appear to be correct.

James Howard, his brother Thomas and his brother Benjamin all settled in Kentucky sometime after the Revolution. For a time, they all lived on the Cumberland River in what was then Knox County, probably in the same section that later became Harlan County. James and Thomas both later moved northwards to Quicksand Creek and the Licking River area and many of their descendants today live in Magoffin and Perry Counties. Benjamin Howard remained in the Harlan County area.

According to his application, James Howard's first term of service began in June of 1777 when he enlisted in Montgomery County, Va. His unit marched first to Abingdon and from there to the Long Island of the Holstien River, from there to the Chereokee county crossing the French Broad River at the mouth of Dumplin Creek.

At the time, General George Rogers Clark was attempting to join from the south with this force from Virginia. The Indians sent the army a flag for peace which was not accepted and the army destroyed an Indian town called Temolely and another called Big Island Town.

The army then marched back with some of them going to Ealond Fork and some to Blackamons Fort on the Clinch River at which place James Howard states he remained until after a treaty was made with the Cherokees. He says that he was discharged in January of 1778.

James and Thomas Howard both state that in June of 1778 they enlisted for three year's service against the Indians in Kentucky and on the wabash. The army rendezvoused at the Long Island and took boats down the Tennessee River. From there they proceeded to the mouth of the Ohio River, up the Mississippi River to the Illinois River.

They proceeded up the Illinois to an old town settled by the French on the Kaskaskia River. After arriving at this point, the entire army was commanded by General George Rogers Clark. According to James Howard's statements, their unit was marched back to the mouth of the Ohio where they remained at a small fort at the Yellow Banks.

During this time period, the bulk of the army under Clark captured Vincennes and Kaskaskia and obtained the surrender of some of the Indian forces. The unit then marched to Boonesboro in Kentucky and helped guard that fort. "The inhabitants were much annoyed by the Indians and this year (1780) I was again marched back to the falls after the French came from Canada and the Indians took Martins and Riddle Stations."

That summer there were additional battles with the Indians at "Peccays Plains...after this engagement the Shawnees did not venture out much." Both brothers refer to having built blockhouses in the area in the time remaining before their discharges.

In both applications, mention is made several times of promises of land which they never received. As Thomas puts it, "Myself and brother James agreed to enlist for three years in Virginia and done so under the promise of land as our father having been murdered by the indians and everything taken from us."

The unkept promise of land probably refers to the bounty land warrants which were promised to Revolutionary war veterans by the United States government. Some veterans never received them at all and many of those that did found them to be nearly worthless as various rules and regulations regarding surveying requirements and minimum tract sizes far exceeding the 100 acres the warrants were for made it impossible for most veterans to actually get any land for them. A great many sold their warrants for a few dollars to the land speculators.