Tangents, and looking for intersections, Part 2

Posted on June 26, 2011 by


So, about that Jessie Scout that I’ve been mentioning…

First, Jessie Scouts were known to be of great value to the Union cavalry, but… often it was because they wore gray… not blue. According to this site,

The concept involving the use of enlisted Union soldiers as scouts, in enemy uniform, collecting information while operating in small groups and raids when grouped in larger formations, developed early in the war at St. Louis. These “Jessie Scouts” were named in honor of General John C. Fremont‘s wife, Jessie Benton Fremont, and they accompanied Fremont to Wheeling, West Virginia, early in 1862. Soon after Fremont resigned his command, the scouts came under the control of General Robert H. Milroy until General William W. Averell was assigned command of what was to become the Fourth Separate Brigade, composed of many of the West Virginia regiments formerly under the command of Milroy.

So, that’s essentially who they were, but, the one I’ve been looking into wasn’t from among those who accompanied Fremont to West Virginia. Instead, he was a former Confederate… yes… you read that right… having served in Co. K, 10th Virginia Infantry. What strikes me about this fellow is the way he enlisted early-on (he was enrolled with this particular company, in the service of the Confederacy, in the first round of enlistments, on June 2, 1861). Often, folks judge (or misjudge) this early enlisting as an indication of wholehearted support for the Confederacy (having been among the first to enlist, he was, therefore “one of the first to answer the Commonwealth’s cause in the defense of Virginia and the Confederacy!” Ok, sure… if that’s what you want to believe without scratching beyond the surface…). That even leaves me wondering just how many, who died at Manassas, in July, 1861, may not have been all into the Confederacy thing than some may believe. No doubt, yes, they did, in theory, lay down their lives for the Confederacy… or at least did so wearing Confederate gray… but were they firmly in support of the cause that claims them among their defenders who died in the name of the cause? We’ll never really know, because the answers to that sort of question were buried with them. We can never tell how they may have reacted a year or so later.

For John W. Saylor (the subject of this post), we’re able to see beyond his early enlistment, and realize that despite his being listed as “deserted to the cavalry”, on May 23, 1862 (something which, by the way, isn’t too uncommon in Confederate military records when, for example, those in the infantry opted out of the infantry for the cavalry… and still in the Confederate service), it was bigger than it appears on paper. What Saylor’s military record does not say, is that he “deserted to the enemy” (the more common entry, in Confederate military records, when headed for the “other side”). Additionally, I’ve had the good fortune to know for sometime, that this fellow did something beyond what his Confederate service record states, for, in another document, dating to sometime around 1913, several veterans from Page County compiled a roster of former local Confederates, and for Saylor, they noted… “Deserted, joined the Jesse Scouts and had the impudence to return after the war on a visit.” This guy had, no doubt, irked a good many Page County Confederate.

It leaves a lot of questions. Did this guy think, prior to enlisting, that he really didn’t support the Confederacy, and only enlisted out of peer pressure? Or, did he, perhaps, actually believe, at least to some degree, in the Confederacy, and have a change of heart… for any number of reasons? Hard to tell, but it’s still quite an interesting story, and leaves much to ponder.

Anyway, we first see references to a John W. “Sailor”, having been tried for murder in Winchester, VA., on February 2, 1863, under Special Order #17, dated February 5, 1863 (in Milroy’s Division). Whether it was our John W. “Saylor”, I can’t say for sure just yet, but he was inevitably released from arrest by order of the President, under General Order #257, dated August 1, 1863.


Another set of records show that our John W. Saylor enlisted in Company C, 3rd West Virginia Infantry (6th West Virginia Cavalry), on July 6, 1863, at Philippi, W.Va. This, of course, leads us to believe that Sailor and Saylor were not the same man… however, knowing how Civil War era military records can be, enlistments have been known to have been backdated from time to time. Nevertheless, Saylor was detailed as scout under Gen. W.W. Averell. Saylor served out the rest of the war wearing blue (and, of course, it can be safely assumed, I believe, that he donned gray in the name of the Union :), and was mustered out, according to records, in Washington, D.C., on September 13, 1866 (to date May 22,1866, at Ft. Leavenworth, KS).

Apparently a restless fellow, Saylor enlisted again, in Winchester, Virginia, in 1867, with the 5th U.S. Cavalry, and was sent to Fort Cottonwood (McPherson), Nebraska, and later to Fort David A. Russell, near Laramie, WY.

In later years in Winchester, one “John Saylor” was later described as “an old Indian fighter”, and was reported to have married (a second time, apparently having become estranged from his first wife and children) and returned to Winchester after 1880; likely the same person. He later applied for and received a pension for his U.S. military service.

Buffalo Bill Cody

So, that whole affiliation with the Jessie Scouts is interesting enough, but, I have to say, his postwar affiliation with the 5th U.S. Cavalry, and forts McPherson and Russell, have me equally as fascinated with this man’s life (this is where the “intersections” part of this post comes in). You see, since he did enlist in 1867, that affiliation has strong potential for having connected him with some rather interesting people in the American West, especially if he enlisted under his previous occupation as a scout. It just so happens that, the 5th U.S. Cavalry, while at Fort McPherson, employed the services of one Buffalo Bill Cody AND John B. “Texas Jack” Omohundro. Cody was serving as a scout, while “Texas Jack” was hired on as a trail agent and scout.

"Texas Jack" Omohundro... quite the "dandy", I must say...

So, did John W. Saylor cross paths with “Buffalo Bill” and “Texas Jack”? I’m hoping to know a bit more once his pension record is in hand. If he did not return to Winchester until after 1880, as the newspaper clipping suggests, the chances seem pretty good. It also leaves the imagination to wonder a bit… if “Texas Jack” ever engaged Saylor in conversation, did their Civil War service ever become a topic? If so, was it less than pleasant? After all, “Texas Jack” wasn’t a Texan at all, but was a native Virginian, born in Palmyra, in Fluvanna County, Virginia, and had served in Co. G, 5th Virginia Cavalry (legend has it that Omohundro was a scout for J.E.B. Stuart, but I’ve got a hunch that was more fluff than truth… and fluff made for more interesting characters in the old West, especially considering “Jack” later gave up the scouting business for the acting business).

Fact is, “Jack” only enlisted in February 1864, having become eligible for service under the 3rd Confederate Conscription Act. He was present in April, but was absent, sick, in June, with no further record of service after that. So, in truth, was “Jack” an unwilling Confederate, like Saylor? Not so, says the evidence. After all, many of Jack’s cousins were in Co. G, and Jack’s own brother, John Orville Calhoun Omohundro, had been serving since April 1863, made 2nd sergeant, and was listed as commanding his company (as a sergeant!) in May 1864. He was wounded in the right ankle at Winchester (yet another intersection… but purely coincidental, when it comes to Saylor) in September 1864, and was promoted to 2nd lieutenant for gallantry in that same action. He was paroled in May, 1865, though his brother appears to have no such parole paperwork on the books.

So, certainly, the irritants were in place between “Jack” and Saylor, but who knows if they interacted, and especially interacted at that level.

Custer and the Duke, after the 1872 hunt

Also of interest in Saylor’s career with the 5th U.S. Cavalry, is the possibility of his presence during Grand Duke Alexei Alexandrovich’s visit to Fort McPherson, in 1872, and the subsequent buffalo hunt, in which Saylor may have had a chance to catch a glimpse of some old familiar faces from his days in the 1864 Shenandoah Valley Campaign… Sheridan and Custer being present.

Saylor’s days, in the shadow of Custer, may not have ended there, for in September, 1876, the 5th U.S. Cavalry played an instrumental part in the Battle of Slim Buttes (again, under the command of a familiar face from the 1864 Valley Campaign days… Wesley Merritt), the first significant victory for the army after the loss at the Battle of Little Bighorn.

It may all come together, and it may not, but, if it does… to think, this former Confederate private… and later, Union private who may have experienced all of this, lays quietly in a simple grave in the Winchester National Cemetery. If it doesn’t all tie together, it sure does make for the setting of one heck of a Western novel!

Saylor's grave, at Winchester National Cemetery