John B. Gregory according to his own testimony was born on March 26, 1844 in Smith County, Tennessee. He was the fifth child of John D. Gregory and Sarah "Sallie" (Harper) Gregory. The circumstances of this family residing in Smith County are not known but from historical documents it is clear that the family spent most of it's existence in Sumner County, Tennessee. The late family historian, Hayden Honeycutt, believed that John B.'s full name was John Bell Gregory. No definitive proof exists but if so perhaps he was named for Tennessee politician John Bell (1797-1869). John Bell was a lawyer and a member of the Democratic party who later became a member of the Whig party. John Bell became Secretary of War in 1847 under President William Harrison's administration. In 1860, he would be the leading presidential candidate of the newly formed Constitutional Union Party. After losing the election he gave his support to the newly formed Confederacy. Whether or not John B. was named for John Bell it is clear that the partriarch of this family, John D. Gregory, named many of his children after prominent Tennessee and Southern politicians. Some of John B's siblings were: Andrew Jackson Gregory, James Knox Polk Gregory, George M. Dallas Gregory (George M. Dallas was Vice President in President Polk's administration), and Thomas Jefferson Gregory. It is interesting to know that John D. Gregory and his family were illiterate being unable to read or write but from the names of the children it is obvious that the family did have an interest in current affairs.

Tennessee was the next to the last state to secede from the Union and the last state to join the Confederacy. The state opposed seccession even after South Carolina had fired on Fort Sumter. However, when President Lincoln called for 75,000 troops to invade the South and quell the rebellion Tennessee along with three other upper southern states (Virginia, North Carolina, and Arkansas) were incensed enough to secede. Sumner County, Tennessee was a hotbed of southern sentiment. The patriarch of the family, John D. Gregory, went to Nashville, Tennessee and enlisted as a Private in Company B of the 18th Tennessee Regiment of Infantry, which was composed of men from Davidson and Sumner counties. He did not live long enough to experience one battle. His regiment was sent with the part of the Army that occupied Bowling Green, Kentucky. The winter of 1861-62 brought death to literally thousands of the ill prepared troops and John D. Gregory fell into that number. Family lore says he was accidentally scalded to death. Some dead soldiers were shipped to their homes and many more were buried in burial sites all over Bowling Green. The exact location of John's burial site is not known but with the help of a Kentucky Sons of Confederate Veterans representative, Stephen Lynn King, a government military marker was placed in the Confederate section of the Fairview Cemetery in Bowling Green, Warren County, Kentucky in June of 2003. The eldest child of the John D. and Sarah family and thus the oldest brother of John B., William Alexander Gregory, enlisted as a Private in Company E of the 24th Tennessee Confederate Infantry. Like his father's regiment (18th) the 24th first trained at Camp Trousdale in Sumner County, Tennessee and then it was sent with the part of the Army that occupied Bowling Green, Kentucky. William did not succumb to the winter of 61-62 in Bowling Green nor did he receive wounds in his first major battle, the Battle of Shiloh, April 6-7, 1862. However, on October 8, 1862 at the Battle of Perryville in Kentucky he was shot through the left foot by a Union minnie ball. He was carried off the battlefield by Sumner County comrade T. J. Moncrief. He was captured by the Union army and in May of 1863 he tried to escape hobbling on his wounded foot. He made it as far as Mercer County, Kentucky before the Federals captured him again. He was described in a Federal report as being 5ft. 5in., having hazel eyes, dark hair, and a dark complexion. William spent a few months in POW camps such as Camp Chase, Ohio and Johnson Island, Ohio and he was exchanged in August of 1863. He spent the remainder of the war as a train nurse in Georgia loading and unloading wounded soldiers. He surrendered in May of 1865 and his wound afflicted him the rest of his life. He was awarded a Confederate pension by the state of Tennessee and when he died in 1904 his foot and leg had perished away. He is buried in a private cemetery in Westmoreland, Sumner County, Tennessee and the family is currently attempting to get a military marker for him.

In October of 1861 John B. Gregory crossed the Sumner County, Tennessee border and entered Kentucky. He traveled as far as Bowling Green and on October 7 he enlisted as a Private in Company F of the 6th Kentucky Regiment of Confederate Infantry. In time, this regiment would become a unit in the famous "Orphan Brigade". It is not known why John B. joined a Kentucky outfit but perhaps he was visiting his father and brother and while there he decided to enlist. John was listed as being 20 years old and being 5ft. 8 in. tall. John was permanently and seriously wounded on the second day of the Battle of Shiloh, April 7, 1862. The Confederate Army retreated to Mississippi and they took John with them. A Union minnie ball had entered John's right arm near his elbow and traveled upwards for 2-3 inches and had not exited his arm. The minnie ball was not to be removed until four years, four months, and six days later. While in Mississippi, John was transferred to Company I of the 6th Kentucky Infantry and on September 9, 1862 he was paid and honorably discharged on account of his wound and the illness that followed. The surgeons declared he had what was called Septeomia on which affected his lungs and later his eyes. Years later he would go blind. John remained in Mississippi for the remainder of the war and in his words "was unable to do anything". He very nearly escaped death and no doubt suffered a great deal.

John never took the oath of allegiance to the United States government at the end of the war. On June 30, 1868 in Franklin, Simpson County, Kentucky John married Harriett Ellen Odell in the home of the bride's father. Between 1869 and 1882 the couple had seven children: Dora, John, Graham, Henry, Harvey, Shelby, and Irvin. On May 4, 1897 John like his brother William applied for a Confederate pension from the state of Tennessee. He recalled how he enlisted in Bowling Green in 1861 and he recalled his officers:

James H. Lewis - Colonel
M. M. Bagley - Captain
M. W. Paige - 1st Lt.
Moses Smith - 2nd Lt.
T. L. Milligan - 3rd Lt.

He also recalled his surgeons: Dr. Stevenson and Dr. John Vertruse. Touchingly, his former 3rd Lt., T. L. Milligan who was then an attorney at law in Gallatin, Tennessee helped him in the application process free of charge. Former comrades such as T. L. Milligan, O. H. Foster, and G. P. Grainger testified to him being an honorable soldier and also that they believed his blindness was a result of the wound thirty years ago. John's pension was accepted and in 1904 he moved from Sumner County, Tennessee to Robertson County, Tennessee. In 1908 he had a small farm worth $750 with a mortgage of $900. He died on December 29, 1916. He was buried in Sulphur Springs Cemetery, Simpson Co., KY. In 1917, his wife Harriett applied for a Confederate widow's pension. She stated she had no personal property. She sent the pension board her copy of her marriage certificate and touchingly on the corner is written, "please send back to me - Mrs. John Gregory". Harriett died on 16 Jun 1937 and is buried in Sulphur Springs Cemetery, Simpson Co., KY.

In conclusion, John B. Gregory and the family of his youth did it's duty but paid a heavy price. The father, John D. Gregory, died and is buried in an unknown soldier's grave. William Alexander Gregory and John B. Gregory were both wounded and permanently disabled. The wounds not only affected them physically but economically as well as they were not able to be fully efficient on their farms and they and their families lived in poverty and had to have the assistance of pensions. There were memorable moments for this family while in Sumner County in this era such as the time when Confederate General John Hunt Morgan with the assistance of the citizens of Gallatin demolised the South Tunnel. There were also sad memories of the atrocities the citizens suffered under the Federal General Eleazar A. Paine while he was in charge of the occupied area. These Gregory men and their wives, sweethearts, and children could certainly appreciate a comment made decades later by a member of the 18th Tennessee Confederate Regiment to one of his comrades, "we did not call it quits like some but until the end remained TRUE Confederates."