Deadliest Fiction Wiki
Jesse James vs Al Capone.png

P.S. I think I got enough support to rematch this Deadliest Warrior classic (see post). This has become one of the battles in that show that I disagreed with. Not because of who won but mostly because of the inaccuracies.

Jesse James: Gunfighter and America's Most Infamous Robber


Al Capone: Bootlegger and America's Most Brutal Gangster

Who is deadliest?

Jesse James


Jesse James was born September 5, 1847 in Missouri.  He and his brother Frank gained their skills as bushwhackers during the Civil War. When the war ended the two allied with former fellow soldiers and bushwhackers to form the James-Younger Gang.

The James brothers were most active with their gang from about 1866 until 1876. On April 3, 1882, Jesse James was killed by Robert Ford, who was a member of the gang living in the James house and who was hoping to collect a state reward on James' head.


Melee Bowie Knife A single-edged knife that can be 12-inches long with a clip joint. Designed as a combat/utility knife, it can also be thrown. Jesse James infamously used it to to threaten to slice a bookkeeper's throat in Northfield.
Short Range Smith & Wesson New Model No.3 A single action top break revolver that fires .44 S&W Russian, a gun notable for its game-hunting power. It has a 6-round magazine. Jesse James is also knowledgeable in pistol-whipping as seen during the Raid at Northfield. Fun fact, this was the same gun that was used to assassinate him.
Medium Range Spencer Carbine A lever-action with a falling block breech-design. It has a 7-round tubular magazine located at the butt stock. Unlike the Henry and the Winchester rifle, the hammer has to be manually cocked in order to fire. It fires the .56-56 Spencer. Jesse James and his gang used it during the 1872 Columbia bank robbery.
Long Range Winchester Rifle The classic lever-action Winchester that fires the .44-40 Winchester at 200 yards. It has a 15-round tubular magazine (manually reloaded) which can be emptied quickly at 60 seconds.

Al Capone

Al Capone 2.jpg

Alphonse Gabriel "Al" Capone, nicknamed Scarface, was an American mobster and crime boss of the infamous Chicago Outfit during the Prohibition era. He orchestrated the deadly St. Valentine's Day Massacre, which earned him the title of "Public Enemy Number One".

Although he was never successfully convicted of racketeering or bootlegging, Capone's mobster career was effectively ended in 1931, when he was indicted and convicted by the federal government for income-tax evasion. He was sent to a series of prisons, including the infamous Alcatraz. He would be released on parole in 1939, but his time as a mob boss was already over. He died of cardiac arrest in 1947.


Melee Baseball Bat An improvised club made of ash wood and can reach lengths of up to 42 inches. The width of the thickest part is 2.75 inches in diameter. Al Capone once used such weapon to beat the heads of two of his men (who were rats) while eating spaghetti dinner.
Short Range Smith & Wesson .38 A double-action swing out cylinder with a 6-round magazine. Al Capone once owned a pear-grip gun in 1928, which he carried around in Miami Beach. The same type of gun were used by the Chicago Outfit to kill Brooklyn crime kingpin Frankie Yale.
Medium Range Pump-Action "Repeating" Shotgun Shotguns were used during the St. Valentine's Day Massacre but it is yet to determine what type was used. Historian Elyse Luray believed it to be a pump-action shotgun that can fire 6-7 rounds of 12 gauge shells. Most of these shotguns have shorter barrels in order to be hidden in waistcoats.
Long Range Thompson M1928 The classic submachine gun, aka "Tommy Gun", that fires .45 ACP in 50-round drum magazines. It has a foregrip and a pistol grip to keep the gun balanced while in auto-fire. The gun was used infamously by the Chicago Outfit to kill 5 members of the North Side Gang.


X-Factors Jesse James Al Capone Reasons
Experience 80 70 Both men lived very violent lives. While some specific parts of Jesse James's life in the Civil War is contested, historians generally believed that he did fought in said war. He was not a professional soldier but he was an irregular bushwhacker under the command of Bloody Bill Anderson and Archie Clements. Jesse James and the other guerrillas made life a living hell for many Yankie Bluebellies, as well as other partisan fighters loyal to the Union. After the War, Jesse James would continue his fighting careers against lawmen, Pinkertons, and even against armed townsfolk and other bandits (like Ed Miller). His robberies, from Columbia to Northfield, showcased his tactics, such as being swift, using disguises, and a trail of horses for a quick getaway.

Al Capone was less violent. Although he orchestrated killings, he seldom participated in it. The only record that we have of him killing someone was the time he beat two of his own men to death with a baseball bat. We don't even know if he has shot anyone. The same can't be said against his own men though. During the Bootleg Wars, the Chicago Outfit was a suspect in numerous shootouts, kidnappings, and assassination. Most of their battles were against the Irish North Side Gang (they were predominantly Italian). Some members have also fought against the police, most notably John Scalise and Albert Anselm who killed two police officers during the Western Avenue shootout.

Logistics 75 90 Unlike most desperadoes, Jesse James and his gang were actually born wealthy, leading to their mystique as "bold robbers" and "gentlemen bandits". Jesse James himself owned a farm, cattle, and small businesses. Being independently wealthy, Jesse James and his men managed to buy their own arms. He was described by Ron Hansen as "someone rich and leisured, who had the common touch." Unlike Al Capone, Jesse James had members that were experienced bushwhackers, and family member/relatives that were loyal to him and vice versa (at least, before the Northfield Raid).

However, this does not compare to the amount of money Al Capone had. Some say the estimated net worth of his empire would be $1.3 billion as of today from his liquor and gambling businesses. He can procure arms from small pistols to machine guns, as well as afford armored cars, police uniforms, and bulletproof vests. He's rich enough to bribe many to him, to the point that during his trial, the judge had to change the jury since the previous ones were all bribed. Unlike Jesse James who died in 1882, Al Capone had the advantage of smokeless gunpowder.

Brtuality 80 75 Both men were brutal and were not shy of killing even unarmed defenseless men. Jesse James combines his brutality with his love of the Confederacy and mental health problems. He once killed someone in cold blood for mistaking him for somebody else. He and his gang killed an innocent bookkeeper and an immigrant laborer for no particular reason. This is made worse by the fact that he was addicted to laudanum. He was a family man though, and was a loving husband to his first cousin (whom he married when they were young) and two sweet children.

Al Capone is not much any friendly too. That person would kill even his own men who had betrayed him. He'll order the the torture and assassination of key enemy gang leaders, and wouldn't think twice of telling his men to gun you down while you're facing a wall. That being said, he never killed anyone who didn't need killing. Unlike James, civilian casualties during Al Capone's reign were little to none. He was a businessmen after all. Also, he was a devoted father. When he learned that his son was born deaf, he actually went and learn how to do sign language in order to be able to interact with his son. He even ordered soup kitchens to feed poor people in Chicago three hot meals a day (though these soup kitchens came from illegal ways).


  • Battle takes place in a city street, a place both warriors knew well. One side of the street belongs to Jesse James and the other to Al Capone. There will be 5 men on each side and the street will be littered with buildings, trees, and other covers both could use. Battle will be to the death.
  • There will be no horses, cars, or any other weapons besides what I have listed above.


Jesse James: Red.pngRed.pngRed.pngRed.pngRed.png

Al Capone: Blue.pngBlue.pngBlue.pngBlue.pngBlue.png

It was a warm afternoon in a dusty city street, somewhere in the urban Midwest, United States. The air bend and wave as the heat made it dance. Moisture had become extinct and the pavement was dry and dusty. It was like hell had risen from the ground to make the people suffer. Then again, with the violence that had been a nature of humankind, hell might as well be the Earth itself.

Al Capone and four of his men were doing their usual business. Large trucks would come in from the Southwest bringing liquid gold from Appalachia. The trucks docked into the side of a street as men came in and strip it off its produce. The products were then hauled to a warehouse to be stored and protected from the eyes of civilians, police, and their fellow badmen. But heck, who would be dumb enough to mess with Al Capone's gang? The dreaded Chicago Outfit itself?

Unfortunately, the world would grant such request...


As the bootleggers worked, they heard the clapping of hooves. It was a peculiar sound, for they were born at a time where horses had left the city streets and migrated to the farms. Yet there was no denying it. Soon, they stared at a group of five men, riding horses like they were cavaliers, wearing slouch hats and white duster coats. The men out of time dismounted off their horses and tied them up a post, before going to a saloon.

"Who the hell are they, boss?" one of the bootlegger asked.

"How the hell should I know... those weirdos..." replied Al Capone. Still, curiosity did took a hold of him. Not to mention those braces of pistols and rifles they were carrying which could mean danger for his crew. "Does any one of you clowns want to check out them out?"

"I'll volunteer, boss," another bootlegger said.

Inside the saloon, the horsemen took no time in making the establishment their own. They grabbed a table and dropped all the cash they made robbing banks, trains, and stagecoaches. There could be hundreds of thousands from their adventures. "Waiter!" one of the men yelled. "Bring us here something to smooth our kisses, will ya?! And put some god damn music in this cesspool!"

The man who yelled was none other than the leader of the group, the outlaw Jesse James. His gang was the most notorious gang that had ever walked the Western territory: the magnificent yet brutal James Younger Gang. No gang was as charming, sophisticated, and bloodthirsty as they were. And they lived up to their name as well, leaving blood and weeping in their wake.

The moment they heard the screams of Jesse James, the establishment did their best to give their best whiskey and brandy. The musician did his best to play his Mozart right. Anything to get something out of that big pile of cash. Everything so these folks could get through this afternoon alive.

"Hey Jesse," one of the bandits said. "See that guy on the door?"

Jesse subtlety looked at the corner of his eye. There he was, the tiny peeping tom spying on their group. Jesse made a smirk and tipped his hat. He then said, "Check this out, boys," before heading out.

The gangster was busy staring at the table full of cash to notice James approaching him. Who were these people? He thought.  That's a lot of money. Were they a rival gang? Do they belong to Bugs Moran? But as he continued drowning his mind in thought, the saloon door smashed his nose, making him tumble down. The bridge was wrecked from that slam, and he cried with a bleeding broken smeller.

"Oh, dang it! Didn't see you there, fella!" Jesse James said with a smile. "You alright? Friend?"

"Fuck you! You just broke my nose!" the bootlegger yelled. "Watch where you going!"

"Ah shitfire, I'm sorry. Here, let me help you out."

Jesse James then grabbed the man to his feet. And as he did so, he saw the others - presumably this man's friends - looking at them. They looked mean and tough, and many of them carried an assortment of arms. Jesse James felt the tingle of adrenaline; the sweet hungry tension of action. He gave the bootlegger one final smile before saying, "And you should look out for who you are spying at."

With a flick of his wrist, Jesse draw his revolver and shot the man in the kidney. The man went down yelling in pain and clutching his abdomen, now leaking red and yellow fluid. It was a death shot and a death sentence. Blue.png Before Al Capone and his men could retaliate, Jesse James emptied his revolver at them before retreating back to the saloon.

"Get your guns and smoke those sons of bitches!" Al Capone yelled as he loaded a fresh drum mag to his tommy gun.

"Holy hannah! Hahahahaha!" Jesse James laughed as the people inside went frantic. "The hell happened?!" one of his bandits asked.

"We're back in action, boys!" yelled Jesse as he ordered them all to grab their rifles and cover all windows and doors.


The Chicago Outfit unleashed their submachine gun at the saloon. The gunfighters’ poor beasts could do nothing but catch bullets as they tried to escape their leashes. While the brick wall withstood the fire, glass and other debris rained down on the James-Younger Gang. "What the hell?!" Jesse yelled. "Are those... handheld gatlings?!"

"What are we going to do?!" yelled one of the bandits. But as soon as he bellowed that powerful question, he accidentally lifted his head a little, enough for two bullets to enter his dome, killing him. Red.png "Ah shit..." remarked Jesse.

Al Capone loaded up another fresh mag after emptying his. He then yelled, "Get inside that house, now!" His men then charged towards the single door of the establishment, firing their weapon as they go. But it was a decent distance, just enough for the bandits to peek out and take aim. Their Spencer and Winchester rifles started to hit them home, making the bootleggers retreat. Sadly, one of them was hit by sniper in the neck, killing him. Blue.png

"No sand, boys!" Jesse celebrated. "No sands! These people can't even hit us accurately with them fancy guns."

"Dammit!" Al Capone cursed. As his men continued to fire, their submachine guns sprayed aimlessly while rifle fire poke at them from their cover. The syndicate leader knew he had to do something. Such a stalemate was bad for business. With people running away for their lives, gunshot filling the air, it would not be long before the law caught up with them and spell their doom. Yet again, as a man who practiced the ways of the Cosa Nostra, he would not let the deaths of his men be unavenged either.

"You!" Al Capone pointed towards one his capo. He then pointed him to one of the empty trucks that was used to deliver liquor. "Get in there and use it to ram that place. We'll cover you."

"Y-Yes boss!" the bootlegger said. He climbed up the truck and pressed on the accelerator. As he shifted gears, him and both parties could feel the speed increasing. Jesse James saw what he was doing and aimed his Winchester rifle. The bandit scored a direct hit to the guy's heart, killing him. Blue.png Yet it was too late, as the truck continued to move, crashing into the saloon. A poor bandit was hit by that truck, pushing him down and crushing his whole body flat on one of its large wheels. It was a painful death. Red.png

"Come on! We don't got all day!" Al Capone ordered his remaining man to charge towards the now open saloon. When Al Capone and his man finally got inside, they saw one of the bandits, his ribs cracked from a direct impact from the truck.

"H-Help... me..." the bandit pleaded as blood spat out of his mouth.

"Wanna do the honors?" Al Capone said to his bootlegger. The bootlegger shot the man with a healthy dose of buckshot to the face. Red.png Suddenly, Jesse James and his remaining bandit burst out of the second floor in a blaze of glory, yelling like crazy. Capone’s gangster was hit multiple times in the chest from the bandit's revolvers. Blue.png Al Capone managed to draw his revolver in time, shooting a bandit and making him fall comically from the balcony. Red.png

Jesse James then turned his revolvers on him. Al Capone took cover behind a wooden column and kept firing. As his revolver ran out, James jumped out of the second floor and landed to near to where Al Capone was, before hiding behind a table. All the money they'd made was scattered all throughout the floor. But Jesse did not mind. He only cared for blood now.

Al Capone, however, was prepared to propose something different. "You stopped shooting?" he asked. "Guess you also ran out of bullets, huh?"

"Shut up carpet bagger..."

"Listen to me! I have heard about you. Hell, I've used your name once. Maybe we can have a deal? You're a Southern gentlemen, are you not?"

"I don't make deals with plump bastards."

"Maybe you'll like this one. You see, I've run out of bullets too. Maybe we can settle this the honorable way instead. Let’s finish this like men!”

Jesse James once again, laughed at what he was experiencing. This day could not get any better. This will make a great story for Frank and his family. A carpet bagger, challenging him, a Southern gentleman, to a fair fight.

"Alright then..." Jesse James said as he drew his bowie knife and got off his cover. Al Capone himself grabbed a Louisville Slugger decor that fell from the column.

He then stood up and approached Jesse, his bat ready for battle. "Let's dance, cowboy."

Capone made the first swing, making Jesse back away as its superior reach almost got him. Jesse then made a thrust with his knife at Capone’s belly but the gangster dodged it. Capone countered by smashing the butt of his bat at Jesse’s chest, scoring a direct hit. Although winded, Jesse made a wild swing as Capone tried to get close, cutting him in the cheek. Pissed, Capone hit Jesse in the stomach, before wrapping the bat around the gunfighter’s neck.

“You are dead!” he yelled.

“Ha! Show it, then!” replied Jesse as he flipped Capone from his back and unto the ground. Capone quickly got up, making Jesse retreat. As he retreated, he tried to throw his bowie knife. Capone felt the sharp pain and blood gush out of his shoulder, but continued on as Jesse was finally cornered.

“Not so tough now are you, prick!”

“Woah, partner. Let’s talk about this…”

A hard swing to the temple got Jesse landing on the floor. As the young bandit bled, he muttered, “My wife… my kids…” But it was all for naught, as Capone mercilessly crushed his head like a watermelon with his bat. Jesse's body convulsed, rattled, before the remaining air finally left his caved chest. That’s what you get for messing with Capone's business.

Winner: Al Capone

Expert’s Opinion

Al Capone won because of his 50-year tech gap against Jesse James. Although the bold robber has experience, Capone’s technology was too much for them to handle, not to mention the automatic weapons, superior mid-range weapons, and smokeless gunpowder advantage. In a battle where there are no quick draw bullshit, Al Capone won with his tommy gun.