At about this time, the Civil War intervened in the 'family pranks.' Coates said that Old George, who 'had been a staunch Whig all his life, boldly announced himself as a Union man, as did his sons. There is one puzzling item connected with this contention. At one point, in an attempt to have one of the numerous horse-stealing charges against him dismissed, George Lewis Underwood said he was a Confederate soldier at the time, just doing his duty. One wonders if young George was trying to impress a judge who may have been a known Southern sympathizer?
Old George and his sons, who did appear on Carter County's militia lists, seem to have formed their own little guerrilla band with two main purposes in mind, which were picking off Confederates and supplying the Union Army with horses. Coates says they became so successful in their enterprise that the Confederates on a number of occasions sent hand-picked forces of rebels (including Morgan's Raiders), with orders to slaughter the Underwoods, but most of these raids failed and the southerners almost always suffered substantial losses in their many futile attempts.
Finally, 'Eastern Kentucky References' quotes a story in "The Vanceburg Courier" of 16 Jan 1878, which said that in the fall of 1962 Morgan either burned or confiscated all the Underwood property and holdings and drove the family across the Ohio River to Portsmouth. A local Carter County doctor who, this compiler feels was sympathetic to the Underwoods as can be seen on a later occasion, said Old George, because of this persecution of his family, swore vengeance and, from that date on, proceeded to carry out his threats.
Alfred A. Underwood, who, in the opinion of this compiler, was probably the 'brains of the outfit', once led a band of 20 men on a raid against Maysville, Kentucky, causing more than a little damage to that town and to its Rebel sympathizers. Coates mentions, as do other historians, that the Underwoods, Alfred in particular, were suspected of having connections with the notorious Jesse and Frank James, but that the family later denied this accusation. This compiler questions the denial, which might have been a clever coverup, because of a story told her by Ottie (Underwood) Perry, which would certainly seem to establish a connection.
Ottie said her father, Robert Daniel Underwood, told of a visit by the James brothers to his family's farm in Carter Co., Kentucky. Frank and Jesse were obviously trying to 'lay low' at the time and actually asked to be given work as hired men, which they performed well. One day young Robert noticed that when one of the brothers bent over a large pistol fell out of his clothes. When the 'hired man' went to return the gun to its hiding place, Robert saw that he was wearing other, very fancy clothing underneath his work clothes, for reasons the boy couldn't understand.
When the time came for Jesse and Frank to leave, they tried to pay a large sum of money to Ottie's grandfather, which sum he refused, saying their stay was at his pleasure. This compiler believes the early Underwood family may have known or been connected in some way to the James brothers' earlier family back in Virginia.
It is impossible to list the names of all the persons who fell before the Underwood guns over roughly a 20-year period (1860-1880), but a few victims have surfaced who were victims earlier than the UNDERWOOD-STAMPER feud. James Carey, a Mexican War veteran, was knifed by Jesse Underwood, according to Coates, but Carey recovered, wouldn't press charges and blamed the whole fight on drunkenness. George Trumbo was not so lucky.
About 1867 or 1868, there had been a circus in Wyoming, Bath Co., KY, which had drawn a boisterous crowd from all over the area. After the entertainment, many of the men deported themselves to a local saloon, where an argument soon broke out, though no one afterward remembered over what subject. Jesse, knowing of one sure way to settle the ruckus, drew his gun, taking aim at a person who disagreed with him.
George Trumbo, meanwhile was over in a corner tippling, but minding his own business and not taking part in the fracas. Jesse pulled the trigger but his target ducked and George Trumbo fell dead on the barroom floor. Coates said Jesse quickly decided to depart for Iowa because Trumbo's friends said if they caught him, he'd 'stretch hemp.'
Another victim was brought to the attention of this compiler by Fred Brown and Bruce E. Logan, Jr., collaborators on a book about the MARTIN-TOLLIVER feud, who said that on 17 Mar 1869 Old George and his son, Alfred, shot James Fleming Logan in Greenup Co., KY. Logan later died of his wounds.
The Underwoods didn't go through the 1865-1875 period unscathed either. George Wolfford mentioned that Old George had apparently 'been wounded in Olive Hill by a member of the Tyree family.' One wonders if this could have been Zachariah Tyree, Coroner, who was arrested about this time for refusing to serve warrants on George and Alfred Underwood? In the late 1870s a number of law enforcement officers chose their own arrest rather than come in official contact with any of the wanted Underwoods.
Sometime after Aug 1871 Alfred may have joined his brother, Jesse, wherever Jesse was at that time. George Wolfford found an article in the 'Big Sandy Herald' in 1874, which said, 'Alfred and Jesse (Underwood), two notorious outlaws who have probably stolen more in Kentucky than any other ten thieves, have stolen horses in Kansas and gone in the direction of the Indian Territory.' Once, when the two were on a horse-stealing mission, probably in either eastern Kentucky or in West Virginia, Jesse was shot through the back, captured and jailed.
'Eastern Kentucky References', which quoted 'The Vanceburg Courier' of 16 Jan 1878, said that Alfred, with a forged warrant, went to the particular jail where Jesse was incarcerated, told the officer in charge that he was the Sheriff of Bath County, come to take Jesse to stand trial in said county and, by this rash act, staged a successful jail-break without firing a shot.
On another occasion, word spread that Jesse had died. A proper funeral was held by the 'frieving' family (who were undoubtedly hoping that law enforcement agencies would now stop looking for Jesse), but Jesse fouled up this inventive act himself, by showing up later and being recognized, after all his family's trouble.
One can't help but wonder whose corpse was in the coffin? This compiler believes this trick was tried again, with more success on the second occasion.