A group of soldiers pulls up to a modest white house and goes inside. Moments later, they exit, dragging Drew Dixon, a boy in a dress who is frantically resisting them. The soldiers throw Drew Dixon in a wagon with other boys, one of whom is also dressed as a woman to avoid conscription. At the Dixon home, Mrs. Dixon protests as they search for Drew, who has already lost one son to the war. When the soldiers leave, Drew emerges from his hiding place. Mrs. Dixon and her husband Joe give Drew $100 and urge him to go West, handing him their picture and his brother's watch as mementos.
In St. Joseph, Missouri, Drew is approached by Jake Rumsey who pistol-whips him and takes some of his money in an alley. Jake runs a gang of petty thieves who steal purses and rob children of their pocket change. While Drew is recovering at Reverend Clum's house, Jake arrives to return the purse that one of his gang stole from the minister's wife, Mrs. Clum, hoping to collect a reward. Inside, he pilfers various household items until Drew sees him and attacks, demanding his money back. After a long struggle, Jake finally bests Drew and convinces him that he has no choice but to join his gang.
Jake introduces Drew to his gang: Jim Bob and Loney Logan, Arthur Simms, and the ten-year-old Boog Bookin. Loney demands that Drew demonstrate his worth by committing a robbery and bringing in some money. Drew agrees and claims to have robbed a hardware store, when in fact he simply took $12 from his boot where he is hiding his parents' money.
The gang heads West, hoping to improve their fortunes. At night, Drew reads to everyone from Jane Eyre. When they spy a rabbit, all six of them shoot at it, barely managing to kill it. Boog Bookin declines to clean the rabbit, and Jake demonstrates how to do it, his disgust revealing that he is skinning his first rabbit. The next day, a settler and his wife Min arrive from the West, where they went bust. The settler offers Min to all six boys for $10. Drew declines, citing his morals.
The following morning, Big Joe Big Joe and his thugs, led by Hobbs Hobbs, come upon the boys while they are still asleep. During the robbery, Jake aims his gun at Big Joe, but doesn't have the nerve to fire. Flat broke, the gang tries unsuccessfully to mount a string of robberies, which results in Arthur running away with a stagecoach (which he was supposed to be robbing) and Boog being shot and killed while running with a pie stolen from a window sill.
The gang finally disintegrates for good when the Logan brothers rob Jake and Drew, taking his brother's watch and the horses. Left with only a mule, Jake and Drew wander aimlessly. Eventually, they come across the Logan brothers' corpses hanging from a tree. Big Joe's gang has killed them, and as Jake and Drew bury their bodies, Hobbs leads the thugs to attack them, despite Big Joe's warning that they would bungle the job. Sure enough, Jake and Drew manage to kill all four thugs, and as Drew leans over Hobbs to retrieve his watch, he reveals a hole in his boot. Jake sees a $10 bill through the hole and realizes that Drew had lied about robbing the hardware store. He pistol-whips Drew again and takes the money.
When Drew awakens, he wanders alone, swearing that he'll kill Jake if he ever sees him again. Seeing smoke on the horizon, he investigates, only to find that it was the result of a burning barn, set afire during a raid by Big Joe. Before he is hanged for taking part in the raid, one of Joe's men confirms to Drew that Jake has joined up with the gang. Drew joins the posse in order to get his revenge on Jake.
The posse captures Big Joe's gang, and as Drew guards Jake, he realizes how guilty he is by lying about his money. Jake offers to split $1,000 that the gang has buried. Drew helps him escape during the night, but after a few days of riding, he realizes that there is no buried money. Jake assumes that Drew will kill him, but Drew swears instead to stick with Jake until he has repaid every cent that he owes Drew.
In the final scene, as they approach a town, Jake asks Drew, "So how'd that Jane Eyre turn out in the end?"
> So how'd that Jane Eyre turn out in the end?
Drew replies, "Fine. Just fine."
> Fine. Just fine.
The two boys walk into the Wells Fargo and rob it.
