The Strange Tales and Ugly Travails of an ex-Bushwhacker: Jim Cummins

The Strange Tales and Ugly Travails of an ex-Bushwhacker: Jim Cummins

By Matthew C. Hulbert

Given the recent surge in enthusiasm for all things associated with Missouri’s brutal brand of guerrilla warfare—a phenomenon perhaps best exemplified by guerrilla-related scholarship claiming back-to-back Watson Prizes from the Society of Civil War Historians—we are faced more than ever with a pressing question: what happened to the majority of Confederate bushwhackers after the Civil War? The short answer is actually quite simple. And, by “short answer,” I mean the most logical conclusion we’ve got at the moment. While many of the guerrilla war’s best-known figures—men such as William C. Quantrill, William “Bloody Bill” Anderson, Dick Yeager, Andrew Blunt, and George Todd—were killed during the war, it seems that the vast majority of ex-guerrillas, like the vast majority of their regular counterparts, returned to agriculture and melted peacefully back into post-war society as best they could.

This answer, however pragmatic, does leave its fair share of stones unturned. For starters, many historians—me included—will contend that guerrillas in Missouri perpetrated and bore witness to a different quality of violence than most other Civil War combatants. By that, I mean to say a more personal, individualized and, in many ways, more savage quality of violence. With this in mind, while late nineteenth century sources are typically mum on the matter, it seems likely that symptoms related to PTSD must’ve been rampant among veterans of the massacres at Lawrence and Centralia, not to mention the untold number of other bloody engagements that more or less destroyed the boundary between the “battlefield” and the “home front.” Then there are the well-noted exceptions—the men who, for whatever explanation of motive and intent you subscribe to, weren’t yet ready to replace pistol with plow. Whether you agree with his thesis or not (and I do, for the most part), T. J. Stiles’ Jesse James: Last Rebel of the Civil War shows, at the very least, how perhaps the greatest exceptions to the aforementioned “short answer” are easily the most recognizable and therefore the most misleading cases of post-war guerrilla behavior.[i]

This story focuses on a lesser-known exception to the “short answer”—a contemporary of Jesse James and Cole Younger named Jim Cummins. Robert James Cummins was born on January 31, 1847, in Clay County, Missouri, to Samuel B. Cummins (1799-1854) and Eleanor C. Crossett (1809-1880).[ii] According to Cummins’ second book, Jim Cummins The Guerilla (1908), he joined up with William “Bloody Bill” Anderson in 1863 after Unionists in Clay County tried to force his mother to abandon her home. He recalled: “I had two brothers in the Southern Army who came home to see my mother and she was accused of harboring bush-whackers… They accused my uncle, who had never taken any part in the war, of harboring bush-whackers and took him from the threshing machine and shot him and then jumped on their horses over him and left the prints of the horses [sic] shoes on his body.” Just as a Union officer under the orders of “Col. Pennick” was informing Cummins’ mother of her eviction, Fletch Taylor came in “recruiting for Bill Anderson’s guerrilla company” and Cummins joined rank.[iii]

A sketch of Jim Cummins noting his status as the last surviving member of the James-Younger Gang.

While Cummins argued that Quantrill and his men had been justified to sack the town of Lawrence, Kansas, on August 21, 1863, he also claimed fervently that he had not been present during the attack in which some 150 to 200 men and boys were slaughtered.[iv] Under the command of Anderson in 1864, Cummins did admit to taking part in the pair of massacres that unfolded in Centralia, Missouri, on September 27, 1864. On the morning of the 27th, a group of guerrillas under Anderson stopped a train carrying a detachment of Union soldiers. In keeping with most accounts, the guerrillas unloaded the Union troopers and then executed all but one of them. Later that afternoon, Anderson and a much larger force of guerrillas sprang a deadly ambush on Major A. Johnston’s 39th Missouri Infantry Regiment. After luring the 39th into an open field surrounded on woods by three sides, Anderson and his men poured out of the woods and made quick of Johnston’s regiment which had, for reasons not known, dismounted in the middle of the field to fight the mounted and charging guerrillas on foot. Over 150 of the Union infantrymen (including Johnston) were killed in the massacre; a stone monument located at the rural battlefield lists the names of the dead. While Centralia was likely the highlight of Cummins’ career as a guerrilla, it is the post-war years of his life that are admittedly the most interesting (and entertaining).

Despite his connection to the post-war crime sprees unleashed by various incarnations of the James or James-Younger Gangs in the 1860s, 70s, and 80s, Cummins was never definitively linked to any of the robberies. In 1882, Robert Ford shot and killed Jesse James as part of a state-sponsored bid to assassinate the outlaw. In an attempt to avoid his brother’s fate, Frank James peacefully surrendered to Missouri authorities in 1882. Throughout the course of his defense, Frank James implicated Cummins as a participant in multiple robberies. As a result, Cummins—then living in Buffalo, Colorado—also tried to turn himself in to Missouri authorities to stand trial once-and-for-all. The only problem with Cummins’ strategy was that no one in Colorado actually believed that he was Jim Cummins and Missouri authorities refused to extradite a man they weren’t sure was Cummins. Later in 1887, this time in California, Cummins again tried to surrender peacefully to authorities—and was again turned away for supposedly being an imposter.

In 1902, despite his role in the guerrilla war, Jim Cummins was admitted as a resident of the Confederate Veterans Home at Higginsville, Missouri. In 1907, while attending a reunion of Quantrill’s men, Cummins had an altercation with another of Quantrill’s ex-guerrillas, David Edwards.[v] Though by most reports Edwards had only ridden under Quantrill for a year, he had participated in the Lawrence Raid and had arguably witnessed the worst the guerrilla war had to offer. According to witnesses, Cummins and Edwards had a long history of feuding which allegedly dated back to Halloween night in 1906—when Edwards claimed that Cummins had accused him of stealing a pet raccoon from his room at Higginsville and had apparently never forgiven him. In the middle of the reunion festivities, Edwards raised a pistol to Cummins head and somehow missed his target from just a few feet away. The bullet ended up striking another ex-guerrilla in the foot but did not wound him. After a scuffle, Cummins and Edwards were separated. Local authorities forced Edwards to spend the night in jail—but, as we might expect from a gathering of bushwhackers, the picnic went on as if the shooting had never occurred.[vi]

The brush with death did not motivate Cummins to change or even moderate his boisterous behavior. In 1909, Cummins fought with another, significantly older resident at Higginsville. For reasons unknown, he knocked the elderly Confederate veteran to the ground with a blow from his fist; the old man died the next day as a result of the injury. Even so, charges were never officially filed against Jim Cummins for the assault. On July 9, 1929, Cummins himself died at Higginsville. He was survived by his wife, Ms. Florence Sherwood, whom he’d married in 1909 at the age of 63.[vii]

Clearly the strange odyssey of Jim Cummins should not serve as concrete model for historians reassessing the lives of Confederate guerrillas in the late-19th and early-20th centuries. But Cummins’ story does quickly point historians desiring to add complexity to our “short answer” in the right direction. We’re often so quick to recount the gory details of Lawrence and Centralia, the deaths of Quantrill and Anderson, or the post-war criminal shenanigans of other prominent ex-guerrillas, that we almost inherently overlook the most obvious source: the fact that while many ex-bushwhackers did try to reintegrate themselves back into the folds of “normal” southern society, they also took part in many of the same activities as regular soldiers: they kept in touch with each other, they resided in Confederate homes, and they participated in annual reunions. In short, we aren’t going to learn more about what happened to ex-guerrillas after the Civil War by simply continuing to study the war itself.


[i] T. J. Stiles, Jesse James: Last Rebel of the Civil War (Vintage, 2003).

[ii] 1850 United States Federal Census [database on-line]. Provo, UT, USA: Operations, Inc., 2009. Images reproduced by FamilySearch.

[iii] Jim Cummins, Jim Cummins The Guerilla (Excelsior Springs, MO: The Daily Journal, 1908), 8.

[iv] Cummins, The Guerilla, 57,

[v] As noted by Donald Hale’s collection of newspaper clippings (The William Clarke Quantrill Men Reunions 1898-1929), reunions of Quantrill’s old command were held annually well into the 1920s. Notable attendees over the years included William H. Gregg, Frank James, Warren Welch, George Shepherd, John McCorkle, Fletcher Taylor, George Maddox, and the Noland brothers.

[vi] “It Didn’t Bother Them,” The Kansas City Journal, August 24, 1907.

[vii] Missouri Marriage Records, 1805-2002 [database on-line]. Provo, UT, USA: Operations, Inc., 2007.

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3 Responses to The Strange Tales and Ugly Travails of an ex-Bushwhacker: Jim Cummins

  1. Angela says:

    “In short, we aren’t going to learn more about what happened to ex-guerrillas after the Civil War by simply continuing to study the war itself.” Brilliant work, as usual, MCH. A pleasure to read as well.

  2. JHW says:

    Well done per usual MCH! Ol’ Jim obviously clocked the elderly fellow veteran at Higginsville for an affront–southern honor was alive and well in 1909! How many stories like Cummins’ have you come across? Certainly a fascinating and seemingly neglected perspective of post-war remembrance, as you so eloquently state.

    • MCH says:

      JHW: Missouri can obviously claim its due share of post-war misfits–from Jesse James to Cole Younger to the fictional Rooster Cogburn–but Cummins’ is without a doubt the strangest of the bunch that I’ve encountered. It probably wasn’t unusual for an outlaw to be mistaken by law enforcement officers (a number of would-be celebrities claimed to be infamous gunfighters and were never believed) but for Cummins to survive the war, his criminal career, and then to escape punishment completely (after trying to turn himself in twice!) is miraculous.

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