Jesse James: Famous Outlaw and Gambler

Jesse James is a legend. After serving in the Civil War, he started his life
of crime, quickly becoming one of the most wanted men in the Midwest. To seek
revenge against the Unionists he fought against in the war, he robbed banks,
raided trains, and killed dozens of people. This famous outlaw also had a secret
passion: gambling. Falling in love with card games at an early age, his love of
gambling would stay with him throughout his entire life.

Please continue reading this detailed biography to learn more about Jesse
James’ life. You’ll learn more about his childhood, his love of gambling, his
time spent serving in the military, and his life of crime. We bet you’ll
discover something you never knew before.

Early Life

Jesse James was born in Kearney, Missouri, on September 5, 1847. He had an
older brother named Alexander Franklin and a younger sister named Susan Lavenia.
His father was a successful farmer, and the family was very well-off. They owned
over 100 acres of land, which was a lot for that time period. His father
actually took some of the family’s money to start the William Jewell College in
Liberty, Missouri, which is still a thriving school today.

Money wasn’t nearly as important to his father as his relationship with God,
which is why he eventually became a minister. Following in his father’s
footsteps, James attended church on a weekly basis and would often volunteer to
help out with events that took place at the church. He even considered going
with his father on a mission’s trip to California to witness to the gold miners
over there. It’s a good thing he didn’t go, though, because his father never
returned. James’ father died from the bacterial disease known as cholera,
leaving the family devasted and causing James to turn his back on his faith.

It was also after his father’s death that James turned to the gambling hall
for comfort. He would spend his evenings at the local gambling hall, watching
people drink their weight in alcohol while playing various card games. Although
he was too young to gamble at the time, he did learn how to play card games like
and blackjack. He eventually taught his brother and sister how to play so
that he would have someone to compete against. Playing these card games was
comforting to him, and it helped him deal with the loss of his father.

The Transition to a Life of Crime

Jesse James and his family supported the Confederacy during the Civil War, as
they wanted to continue to use slaves to run their farm. In 1863, their farm was
attacked by Union soldiers that were trying to get more information on the
Confederate guerilla bands. Although the soldiers threatened to kill James and
his family if they didn’t give up any information, they left without harming
anyone. This experience motivated James and his brother to participate in the

They ended up becoming members of William “Bloody Bill” Anderson’s guerilla
unit. This is when James learned how to shoot a gun properly and how to sneak up
on his enemies without getting caught. He would eventually use these skills to
help him live a successful life of crime.

Before his life of crime began, James was shot in the chest during a vicious
guerilla raid. He managed to recover from that quickly and was eager to
participate in what would later be referred to as the Centralia Massacre. James
and a large group of Confederate soldiers attacked Centralia in the middle of
the night and were able to kill 22 Union soldiers who had been left unarmed.
They then proceeded to torture and kill over 100 more soldiers after that. James
was responsible for taking down their leader, Major Andrew Johnston.

Towards the end of the Civil War, James was shot by a Union soldier while
trying to surrender. He didn’t recover from this battle wound as quickly as the
time before. Zerelda Mimms, James’ cousin and love interest, took care of him
until he was ready to get back on his feet again. The two would often play
blackjack together to help the time pass by. Once James was healthy, he decided
to join his brother and some of their fellow soldiers who spent their time
robbing banks as a way to rebel against the result of the war.

A Life of Crime Continues

The first bank James helped robbed was the Clay County Savings Bank in
Liberty, Missouri, in 1866. He managed to rob the bank in the middle of the day,
walking away with over $60,000. In an effort to escape, James was forced to
shoot an innocent bystander who got in the way. The man, George Wymore, became
James’ first murder victim outside of war.

It wasn’t until December of 1869 that James started to get recognition for
his crimes. He had recently robbed the Daviess County Savings Bank in Gallatin,
Missouri. He shot and killed one of the bank tellers, making it known it was to
get back at him for killing his dear friend, Bloody Bill, during the Civil War.
His story of revenge made the front page of several local newspapers, and it
wasn’t long before he became one of the most well-known criminals in Missouri.

James was not afraid to be in the public eye; he actually welcomed it! He
wrote countless letters to the editor of The Kansas City Times in which he
justified most of his actions. The editor, who hoped the Confederates would
regain power in Missouri, chose to publish the majority of his letters. He
portrayed James as a hero for taking a stand against the Unionists who were in
charge of the state government at the time.

The James-Younger Gang

Jesse James and his brother joined forces with Cole Younger and his brothers
to form the James-Younger gang. They also recruited several other Confederates
who they had fought alongside in the Civil War. They stole from banks and
stagecoaches all over the Midwest, eventually working their way up to robbing
trains. In 1873, they derailed the Rock Island train while it was passing
through Iowa and were able to walk away with more than $3,000 cash. That was the
first of many trains to be ambushed by the gang.

The gang hardly ever dealt with the train’s passengers during these
robberies, choosing to take only the contents from the train’s safe instead.
They managed to steal an estimated total of $200,000 from their train robberies
alone. As you can imagine, the Adams Express Company, which owned many of those
trains, was furious. They hired the Pinkerton National Detective Agency to take
down the gang.

Allan Pinkerton, the main detective on their case, chose to send James a
pretty strong message. He traveled to his mother’s house, shooting her in the
arm and killing James’ 9-year-old half-brother. When news got back to James
about this incident, he was devastated. While this didn’t stop him from
committing robberies, it did cause him to lean on gambling for comfort.

He started spending his free time in the gambling halls of whatever town he
was currently staying at. He often encouraged the other members of the gang to
join him. His favorite game to play at the time was Faro. Faro is played on an
oval table with a full deck of cards. The object of the game is to accurately
guess which cards the dealer will flip over. This game is relatively simple and
takes very little strategy, and yet James was somehow very good at it. Winning
Faro on a consistent basis lifted his spirits and helped him deal with the loss
of his half-brother.

The last time the James-Younger gang was all together was when they chose to
rob the First National Bank of Northfield, Minnesota. This bank was located down
the road from a police station, making the robbery almost impossible.
Authorities quickly rushed to the bank once they got word of the robbery and
were able to take the Younger brothers into custody.

While James didn’t get caught, he would have to recruit new members if he
wanted to continue his crime spree. That’s where the Ford brothers came in.
James invited Robert and Charley Ford, two well-known criminals at the time, to
join in his efforts. He was impressed by their abilities and thought they would
make an excellent asset to the gang. Little did he know that these two had
ulterior motives for helping James.

A Tragic Death

Governor Crittenden was determined to capture Jesse James so that the
citizens of Missouri could have peace of mind. He made a deal with Robert Ford
in which he agreed to pardon him and his brother for their crimes if he was able
to kill Jesse James. To make the deal even sweeter, Governor Crittenden also
agreed to give him $10,000.

When James woke up on April 3, 1882, he thought it was just another day. He
was cleaning the house before it was time to leave for his next robbery. He was
standing on a chair to dust off some of the picture frames in his home when Ford
snuck up behind him, shooting him in the head 3 times. Those shots to the head
caused him to drop to the ground; he was dead.

Legends Never Truly Die

While James died that day, his legacy still lives on. His life became the
focus of several novels, including Shot All to Hell by Mark Lee Gardner and The
Last Ride of the James-Younger Gang by Sean McLachlan. There is also an old film
based on his life titled The True Story of Jesse James, which was a huge hit
when it was first released in 1957.

Jesse James had been married to his cousin, Zee, for nearly 8 years before he
passed away. The couple had two children who survived past infancy: Jesse Jr.
and Mary Susan. The two had very few memories of their father, but one thing
they did recall was his love of card games. Once they were old enough to hold
cards in their hands, James started teaching them the basics of blackjack. Jesse
James Jr., who eventually became a lawyer, would always treasure those times he
spent playing cards with his father. While the world may remember his father as
a greedy outlaw, he chose to remember him as a loving father who enjoyed playing