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Top 10 Amazing Outlaws During the American Civil War

Guerilla Fighters During American Civil War
Make sure to line up for your 5th grade outlaw pics during the photo shoot after school.

The Civil War in America was a discerning time of great disagreement and succession. Not only did the South separate from the North, they had wild disagreements in how things should be run in the country. This led to a separation of the Confederate states from the Union states, leading to the American Civil War. While some historians and people may try to confuse as to why the Confederate States of America separated from the Union, it’s fairly clear as to why they did it, slavery being the driving force behind it all.

The war would often be fought right in the middle
of city streets and open fields right outside of small towns. This would not stop the crave lunacy that often follows
with armed combat. This disagreement, along with Union’s ultimate success and the 13th amendment freeing the slaves, led to many unofficial armed units to take matters into their own hands, especially on the Confederate side.
I’m going to be listing the top ten American Civil War guerilla fighters.

Top 10 Guerilla Fighters During American Civil War

1. William C. Quantrill

William C. Quantrill was a Confederate outlaw who was born in Canal Dover, Ohio in 1837. Going by the pseudonym Charley Hart, Quantrill was an American Civil War captain, but he was not captain of a regular band of soldiers, he was the leader of a guerilla band. He is notorious for his involvement in sacking the free-state stronghold
of Lawrence, Kansas where at least 150 people were burned or shot to death.

Quantrill grew up in Ohio, teaching school throughout Illinois and Ohio before moving to Kansas where he would
make an attempt at farming, but to no avail, he moved on. He would later delve into debauchery via negative means of thievery and murder, being charged with the grand theft of a horse and living his life as a vagabond.

When the American Civil War had begun, he chose to fight for the Confederate Army of Missouri, later splitting
off and creating a ragtag gang of guerrilla criminals. This little team of Quantrill’s decided to take part in
mass murder, arson and theft, raiding towns and farms who sided with the Union. His little team was known as
the Quantrill Raiders, later being considered outlaws by the Union forces and an official troop by the Confederate
Army in 1862. This made Quantrill a official captain, and from soldier to outlaw to solder, raided Lawrence in
1863 with great success.

The stronghold was attacked by his some 450 men, being pillaged and burned and with numerous counts of murder. After this, they donned Federal uniforms and slaughtered a surprised detachment of Union soldiers at Baxter Springs, slaughtering about 90 of them. In 1965, Quantrill would end up being mortally wounded after his band of cheaters decided to break up and go their separate ways.

2. William T. Anderson

William T. Anderson, known as “Bloody Bill”, was a Confederate outlaw and bushwhacker who was born in Hopkins
County, Kentucky in 1837. This nut-job took part in the Lawrence and Centralia massacres, taking part in savage
guerilla warfare across both Kansas and Missouri.

As a child, his family moved to Missouri before he later moved to Kansas in 1857, growing up in a pro-slavery
household and experiencing the “Bleeding Kansas” conflict over slavery. By 1860, Anderson had become a property
owner, going into the freight shipping business and trading horses with his father. He eventually went into
stealing horses and attempted to join the Confederate Army, later being attacked by the Kansas Cavalry in Missouri.
This led to a quarrel, leading to Baker, the Anderson’s proslavery judge, murdering William’s brother before
being killed by Anderson in return.

Along with another outlaw, Anderson formed a gang with Bill Reed, robbing and attacking Union soldiers before
joining Quantrill in early 1963. This eventually led to Anderson becoming a lieutenant, partaking in raids
across Kansas and Missouri under his own accord. After one of Anderson’s sisters died, apparently by accident,
he blamed the Union and went off on a rampage, leading to his nickname and reputation for torture and mutilation.

This would eventually lead to the massacre in Lawrence, Kansas, Anderson being a part of this group and acting
in excessive brutality to help loot, burn buildings, and kill many people. Later on, he would be involved in
espionage murders and the raid near Centralia, becoming an infamous outlaw and being killed in a battle in Albany,
Missouri after becoming involved with Jesse James.

Top 10 Guerilla Fighters During American Civil War

3. James H. Lane

James Henry Lane was an American senator and militia leader who was born in Lawrenceburg, Indiana Territory
in 1814. Lane was known for being a staunch supporting of the Union and for being a principal leader of the anti-slavery forces that made Kansas a free-soil state. He was embroiled in the “Bleeding Kansas” conflict, earlier on following in his father’s footsteps to become a lawyer.

Lane would serve in the Mexican-American War as the commander of two Indiana volunteer regiments, helping him
launch his own political career. He would later serve as Lieutenant Governor of Indiana beginning in 1849 and as
congressman in 1853. After this, he moved to the Kansas Territory, becoming a founder of the Free-State party,
in spite of being a Democrat. This led to him to organize free-state militia units throughout the territory to
help defend Lawrence, Kansas, his base of operations. This area would later be attacked by goons, but Lane was there
to help protect it.

After going on hiatus after having killed one of his neighbors, Lane would go on to win elections after Kansas
entered the Union in 1961, being one of the first United States Senators from Kansas and having become a Republican.
He soon became a strong ally to Abraham Lincoln, involving himself by helping form two Kansas volunteer regiments
that would end up fighting the Confederates in Missouri, forming a “Frontier Guard” to protect the White House.

Lane made many enemies, including William Quantrill, which was part of the reason Quantrill attacked Lawrence, Kansas to begin with because of his free-soil politics. Lane would go on to become known for becoming a radical Republican, supporting civil and political equality for African-Americans and helping them flee slavery in Missouri and
Arkansas. He would go on to form the first black regiments as a recruiter before killing himself in 1866.

4. John S. Mosby

John Singleton Mosby, known as “The Gray Ghost”, was a Confederate army commander who was born in Powhatan County, Virginia in 1833. Mosby grew up kind of rough, kids often picking on and bullying him. He later attended the University of Virginia in 1849, noted for his abilities in Classical Studies and shooting a bully straight in the neck before being arrested and sentenced to one year in jail. After being expelled from the university and serving some time, he was released with a pardon from the Governor of Virginia.

During his time in jail, he befriended an attorney and learned a lot about law, being admitted to the bar later
that same year. In 1857, he had established his own law practice in Howardsville, Virginia, later speaking out
against succession during the American Civil War. He ended up joining the Confederate Army as a private, serving
in the Virginia Volunteers. His military ability later caught the attention of J.E.B Stuart, later being promoted
and assigned to Stuart’s cavalry before being imprisoned by the Union and being paroled shortly after.

Stuart later, in 1863, promoted Mosby and gave him command over the 43rd Virginia Cavalry, operating as a partisan guerilla unit. Major Mosby began to conduct a campaign of raids on Union supply lines, being able to appear and disappear at lightning speeds, hence his nickname. He continued his raids, including the mutual murder of prisoners, even after the war had ended, finally disbanding his troops and hiding out before becoming a Republican and campaign manager for Ulysses Grant.

Top 10 Guerilla Fighters During American Civil War

5. Champ Ferguson

Champ Ferguson was a Confederate bushwhacker who was born in Clinton County, Kentucky in 1821. Ferguson is known as one of the most infamous guerilla fighters in the Civil War, causing an understanding of personal revenge.
Ferguson would end up moving to Tennessee in the 1850s, and according to folklore, he and his family were drove
out and publicly humiliated.

This champ would end up gathering a group of armed men and attacking Union partisans and sympathizers after the outbreak of the Civil War in 1861. He was officially considered a Confederate captain with a company of men, even
though he was not formally attached to the Confederate Army. He was recognized for his usefulness and joined
in helping raise a cavalry company.

By 1862, he was associated with the Confederate Army, joining Colonel John Hunt Morgan as a guide during Morgan’s first Kentucky raid. By 1864, he was to help harass William Sherman’s march through South Carolina, going through several commanding officers in his time. He would later participate in the Battle of Saltville, Virginia, slaughtering prisoners of war before being sent to jail for a specific murder. By the end of the war, Ferguson was considered an outlaw, and sentenced as a guerilla before being executed in 1965.

6. Jesse and Frank James

Jesse and Frank James were American outlaws born in Missouri, Frank being born in 1843 and Jesse in 1847, respectively. They were both raised on a Missouri farm, sharing the sympathies of the South when the American Civil War began. Frank joined Quantrill, while Jesse joined Anderson’s guerilla gang, and at the end of the wars, the bands
surrendered, but Jesse apparently got shot several times by Federal officers under a flag of truce.

Afterwards, Jesse and Frank began their outlaw career by robbing a bank in Liberty, Missouri in 1866. Along with
several other men, the James gang robbed banks from several different states, including Iowa, Alabama, and Texas.
They would soon hold up trains, prey on stagecoaches, stores and individuals. The two were eventually forced to
gather a new gang, continuing to rob until Jesse James was murdered in 1882.

Top 10 Guerilla Fighters During American Civil War

7. M. Jerome Clarke

Marcellus Jerome Clarke, known as Sue Mundy, was a Confederate captain and bushwhacker who was born in Franklin, Kentucky in 1844. Clarke is known for being one of Kentucky’s most infamous guerilla fighters. Clarke joined
the Confederate Army early on, being captured and imprisoned in Indiana before escaping and seeing his brother
get shot and blinded. He then swore his revenge and served in the Confederate artillery under the command of John
Hunt Morgan. Later on, Morgan raided Kentucky, leaving Clarke to form a guerilla band that scoured much of Kentucky.

Clarke would become notorious for robbing citizens and burning property, later riding with William Quantrill
during the early 1865 Kentucky raid. Fortunately, this little rascal was eventually captured and hung in 1865,
accused of murder and various other crimes.

8. Charles Jennison

Charles Ransford Jennison was an American guerilla fighter who was born in Antwerp, New York in 1834. He grew
up attending primary school before his family moved to Wisconsin in 1846, later on studying and practicing
medicine before continuing a migration westward to Kansas Territory.

Jennison soon became interested in abolitionist John Brown, later gaining a strong temperament towards proslavery and leading a raid against the proslavery settlers. There were a couple of hangings that Jennison and his men carried out for their slavery convictions, later having a judge forced out of his court for being proslavery.

Jennison would later use the Civil War to his advantage, causing him to focus on pro-secessionist elements of
Missouri. In 1861, he was commissioned to captain of the Mound City Guards and later on as lieutenant colonel
of the Seventh Kansas Cavalry Regiment, widely know as the “Jennison’s Jayhawkers.”

He was assigned to command the western border of Missouri, having been headquartered in Kansas City, adopting a scorched earth strategy of warfare against the Confederates. After having retired to civilian life, Colonel Jennison
returned to action after the Lawrence Massacre and raising a regiment of cavalry to protect the border.

In 1864, he made a foray into Missouri against the guerillas, later engaging Confederates at Lexington and elsewhere to push them back with success. He then enjoyed a successful post-war political career before dying in 1884.

Top 10 Guerilla Fighters During American Civil War

9. John H. McNeill

John Hanson McNeill was a Confederate guerilla soldier who was born near Moorefield, Virginia in 1815. After his marriage he went off to the west, seeking more land and settling in Missouri on a 500 acre farm. Be became a well-respected man and lay minister, being active in the Methodist Church.

When the Civil War started, he commanded a company of cavalry, taking part in at least four battles in Missouri.
One of his sons ended up getting killed, getting captured and later escaping back to Hardy County. Upon his return,
he organized a cavalry known as “McNeill’s Rangers,” having many people from nearby join it.

He was officially part of the Northwestern Brigade, even though they operated independently, becoming a pain in the butt to the Union supply lines in the area and joining in larger campaigns, including Gettysburg. After the Chambersburg raid in 1864, the Confederate soldiers were surprised and defeated in the Battle of Moorefield, the largest battle of Hardy County. McNeill was eventually injured and succumbed to his wounds after a successful attack on a Union encampment in November of 1864.

10. Jim and Cole Younger

Jim and Cole Younger were both born in Missouri, Cole being born in 1844 and John in 1848. As they were growing
up, they witnessed countless violence during the Kansas-Missouri border skirmishes, leading to them witnessing the
Civil War. Cole, along with Jim, would later join the Quantrill raiders, meeting Frank James there as well.

After the war, they formed the James-Younger gang and robbed bands, Cole’s little brother Jim joining in 1868.
The rest of the family joined in, afterwards robbing trains and getting tailed by Pinkerton agents and sheriffs.
Eventually, John Younger died in a shootout with the agents in March of 1874. The gang ended up disbanding after
an unsuccessful robbery at the First National Bank in Minnesota, leaving three dead and Cole, Jim and Bob in prison.

Honorable Mentions: Colonel James Montgomery, Beatty and Dr. Hale, John Mobberly, John Hunt Morgan,
“Stovepipe” Johnson, George M. Todd, and more.

Top 10 Guerilla Fighters During American Civil War

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