Jim Reynolds: Confederate Guerilla

Ever since a Georgian by the name of Green Russell discovered a placer deposit along Cherry Creek and set off the Pike’s Peak Gold Rush, prospectors from Russell’s home state and those surrounding swarmed the burgeoning mining camps of the Rocky Mountains. But in 1861, finding themselves suddenly in Union territory as their southern brothers headed to war, Colorado’s displaced rebels seethed under censorship and their own inaction. They were, as one newspaper put it, waiting for a finger to tap them on their gun-ready shoulders.

That tap, that flurry of instigation happened more than is widely known in the young Civil-War-era Territory of Colorado.

On the morning of April, 24 1861, the people of Denver looked above them to see the Confederate Stars and Bars flying over a Larimer street warehouse. A unionist by the name of Samuel Logan, promptly climbed up and tore the flag to the earth to much applause (despite the influx of southern sympathizers in the territory, the vast majority still paid allegiance to the Union). And so marked the only occasion in the history of the city where a Confederate flag ever flew over the streets of Denver.

In the days that followed the south did not give up on Colorado. Perhaps more accurately, the Texans did not give up on “winning the west.” When war did break out, those sympathizers that did not return home formed militia groups in ming camps around Colorado’s Rocky Mountain range, including Fairplay, Leadville, Canon City, and, most infamously Mace’s Hole near Pueblo, CO. In this hideout recruited southerners grouped, trained, and readied until by the time nearby Fort Garland learned of their presence and immediately shut it down Mace’s Hole boasted over 600 trained rebel soldiers.

Of course, the most conspicuous of the Confederate pursuit of Colorado was Sibley’s 1861-1862 invasion of New Mexico. In late 1861 nearly 3,000 Texans led by General H. Sibley departed El Paso and marched northward into New Mexico with the intent of capturing the pathway of the Santa Fe Trail, and, most importantly, the renowned mineral resources of Colorado and California. Along their quest Sibley and his three-thousand Texans found victory at Valverde, then Albuquerque, and then capitol, Santa Fe (although the latter two were handed over without incident). Just days after sacking Sante Fe however, a force of Colorado Volunteers surprised Sibley in what is called Glorieta Pass (about 15 miles NW of Santa Fe). It was a decided victory for the Coloradans, and the Texans retreated home never again to make an attempt at Confederate “Manifest Destiny.”

Early in 1864 however, with the war still very well anyone’s ball game, one Texan man by the name of Jim Reynolds decided to take his own personal attempt at manipulating Colorado for the good of the Confederacy. Some claimed him to be something of a Confederate Robin Hood, one who stole from the rich and the poor and then gave to the south. Others saw him a stalwart enemy of the Union out to hamper their cause in any way he could. And still others labeled him just another gun-pointing thief, his ruse of giving his booty to a “cause” somehow making him noble. Considering that none of Reynolds loot ever did make it back to Texas and the Confederacy, this latter description is probably the most accurate.

Jim Reynolds was born in Texas in the 1840s and arrived in Colorado’s South Park area around 1863. Here he was a poor worker and one with short dedication. He stumbled from one territorial job to the other – miner, rancher, farmer, bartender, rarely holding a position for more than a few days. And all money he ever made was said to go straight into the bottle.

Perhaps realizing this, Reynolds and his gang turned to robbing. It was more exciting, demanded less hours, and paid a whole lot better. The citizens of Fairplay soon began to notice how the pockets of Reynolds and his men were always fatter each time a wagon was seized up in the mountains.

During one botched robbery attempt, Reynolds was apprehended. But in those days of crude, cabin-style jail-houses, Reynolds promptly escaped, rejoined his gang, and fled the territory.

It was the height of the Civil War and the gang returned to their home state of Texas. Somehow escaping enlistment, Reynolds soon learned that the largest problem facing the southern states was a rapidly diminishing treasury, and so made a promise with some of the Rebel officers to return to Colorado where gold is pulled out of the streams every day and organized security is few and far. He urged them to send him and his posse (this time a larger one) back to this land of South Park he knew so well so that when he next returned it would be with enough stolen Union gold to help the southerners finance their war.

Purportedly commissioned by the Texas Confederate Forces, Jim led his guerillas northward through New Mexico on the long dry stretch back into the central Rocky Mountains. About halfway through the territory, the gang captured a wagon carrying over $60,000. Robbing throughout New Mexico had not been part of the original plan, but most men simply agreed not to allow the opportunity to slip by. And, needless to say, with so much money in so many hands, the gang’s leader Jim Reynolds (sensing a mutiny) immediately found himself re-preaching the virtue of their mission, how the Confederacy needed this money much more than themselves. The gang however, up to their bellies in gold and silver, did not listen and instead split the booty squarely and most of the gang took their loot and departed right there, leaving only nine of the original and most ardent posse members: John Bobbitt, John Andrews, Jack Robinson, Tom Knight, Jake Stowe, Tom Holliman, Owen Singleterry, Jim Reynolds, and his brother John.

The diminished posse reached South Park and convened at Adolph Guirand’s ranch between Hartsel and Fairplay. From there, the posse moved toward Fairplay and began their daily ambushes and pilgrimages. They began small: holding up individuals at knife-point, breaking and entering empty-looking homes, before graduating to wagons and large ranches.

At one such ranch, apparently upset for the lack of treasure found on a victim by the name of Major deMary, Reynolds took the passenger prisoner and forced him into humiliating clothes.

The gang worked their way to McLaughlin’s stage station which was rumored to always keep an abundance of currency on hand. Once there, the gang immediately captured the station, even going so far as to order the station cook to wine and dine them. By the time the passengers had emptied their pockets, all the horses were rounded, and the lockbox had been pried open, Jim Reynolds is said to have made away with upwards of $100,000 from McLaughlin’s station.

The gang did not delay in keeping their good luck rolling, robbing large South Park ranch estates out of thousands of coins, livestock, and collectibles, including the Omaha House, the Michigan House and the famous (but now gone) Kenosha House.

Fairplay, CO

Needless to say, by now a variety of posses existed in Fairplay, all combing South Park for the bandit Jim Reynolds. One such posse man by the name of Mr. Berry, was caught by the Reynolds Gang his first night out. Fortunate for Berry however, the gang was in good spirits that night and, after some teasing let him go.

Released into the night, Berry ran all the way to Junction House, located not far from Evergreen. From there Berry continued into Denver by train with his story.

Although they did not suspect it, several posses were now closing in on Jim Reynolds. As the gang slept unassumingly in the deserted Omaha House, several posses snuck their way – over one-hundred posse men in all.

But in the morning Reynolds sensed danger and, knowing the country around him well, ordered his men to carry all their loot up Handcart Gulch (near present-day Kenosha Pass) and hurriedly build a makeshift camp. A corral was built for the horses, a rockwall mounded for protection to shoot behind and, perhaps most telling of all, a large hole was dug and then inconspicuously covered.

Ultimately it was a posse out of Breckenridge led by one Jack Sparks that noticed the late-night campfires of Jim Reynold’s tree-surrounded hideout. A firefight broke out in the night and, as Sparks’ men pressed forward, Reynold’s men, in the dark confusion, mounted their horses and fled.

At daylight, Sparks’ posse surveyed Reynold’s hideout, discovering the body of Owen Singleterry – apparently the only fatality of last night’s blind bullets. Sparks and his men buried Singleterry, sticking a knife in a tree directly above the                                     gravesite then, failing to notice anything else suspicious at the site, departed.

By now the Reynolds Gang had dispersed all throughout the territory in hopes of evading their posses. Tom Holliman was found asleep in a hotel by Sparks’ Posse and captured. Jim’s brother, along with two other gang members, were given pursuit but ultimately made it back to the New Mexico Territory. It’s believed that Stowe was actually shot during the gunfight at Handcart Gulch and died shortly after, while Andrews met his maker via a saloon brawl in Texas.

As for Jim Reynolds, he and three others retreated into the hills and remained at large for a two days, for on the second day an either very bold or else very desperate Jim Reynolds reappeared in Fairplay, looking for food and water. The men were immediately apprehended, though no portion of the stolen loot was ever discovered.

At this point the story becomes shrouded in mystery. Because Colorado was not yet an official state in the Union at the time of Reynold’s arrest, his case was handed over to the local Union military. One story told is that the army held a secret trial for all the members of the Reynolds Gang and, finding them guilty of conspiring against the Union, sentenced them to hanging.

Fort Leavenworth, KS

Of course, questions immediately arose regarding the military overstepping its boundary. In response, it was decided that Jim and his fellow guerillas march all the way to Fort Leavenworth, Kansas for a proper military tribune. Led by Captain Cree, the 3rd Colorado Cavalry escorted the gang members into the plains.

Amazingly, the very next day the Captain returned to Denver, claiming that he had had no choice but to shoot all five prisoners for they had escaped and were turning on their captors. A few weeks later a traveler on his way to Fort Leavenworth came upon the old ghost town of Russellville. There, strapped hand to hand around one thick elm tree was Jim Reynolds and his remaining posse men – all of them shot to death. Eventually Captain Cree would reveal that never had he actually been given orders to escort the five prisoners all the way to Fort Leavenworth, but instead his orders had been to fatally dispose of them at the first opportunity.

But the most enticing mystery of the legend of Jim Reynolds is still one that looms unanswered today: the yet-to-be-found whereabouts of Reynolds Confederate loot.

Kenosha Pass

Toward the beginning of the 20th Century a treasure hunter named Vernon Crow was out in search of the lost treasure of Jim Reynolds. He retraced the spots between Kenosha House and the other ranches until finally coming upon the infamous Handcart Gulch. There, after pushing for some ways through the thick of aspen and pine, Vernon came upon a large pile of rocks and, the biggest clue of all, a rusted knife handle sticking out of a tree directly above yet another piling of rocks. In one corner of the hideout were the remains of an old impromptu horse corral. Immediately Vernon began to unearth the stone piles, coming upon nothing except deep dirt in the case of the larger mound. Under the second mound under the knife handle Vernon found exactly what he was looking for. Or, that is, exactly what he should have been looking for if he had been familiar with the story. For under those stones lay a bullet-ridden skeleton many decades dead.

Hastily Vernon recovered the grave and departed the area. To this day wherever Jim Reynolds hid his Confederate loot remains a mystery: one waiting for some keen and very lucky hiker in the wilderness around Colorado’s Kenosha Pass.

Newspaper Headlines for Jim Reynolds


August 13, 1864: Lt. J. S. Maynard (AAAG of the District of Colorado) reports that during a skirmish several of Captain Reynolds men have been captured by Lt. Shoup near Black Squirrel Creek (in El Paso County) not far from Pueblo, Colorado;

August26,1864: Newspapers report Captain Reynolds was captured however his brother (John Reynolds) and several others escaped;

September 10, 1864: Newspapers print the “Black List” of approximately 100 suspected local “secessionists” in Colorado;

September 13, 1864: During a special election 75% of Coloradans voted against statehood (4,676 to 1,520);

For several weeks after the special election, many local newspapers reported that the failure of the statehood amendment was due to a very strong “anti-state party”, the majority of which were “Copperheads” (secessionists or Southern Sympathizers).

December 9, 1864: Newspapers report that James Reynolds and several of his men were shot and killed while attempting to escape while being transported from Denver to Fort Lyon by a detachment of Company A, 3rd Colorado Cavalry.