In September, Anderson led his raiders towards Centralia, Missouri to loot the town. They burned most of the buildings and killed several of the residents. Henry was sent with several men over to the railroad tracks of the Northern Missouri to barricade the line. They set up a large pile of railroad ties and waited for the train to arrive.
As the train came to a stop, the brakes squealing, the raiders jumped on board. Henry jumped up on a passenger car and kicked open the door. With a gun in each hand he entered the car and found it full of Union soldiers. He started blasting away, shooting from side to side, killing as fast as he could pull the trigger. The soldiers were caught without any weapons as they were heading home for a furlough. After twelve shots were fired and twelve soldiers were dead, Henry dropped his guns and pulled two more out of his belt. He continued firing until twenty-two soldiers were dead. The rail car was full of powder smoke and the smell of recent death. Henry stood there and calmly reloaded his guns while the other passengers sat there in shock.
After reloading his guns, Henry pointed them at the frightened passengers and several women screamed. He didn’t kill them, however; he simply held out a bag and took every penny that they owned. Not a single person held anything back.
Anderson and his raiders pulled all the bodies off the train and stripped and scalped them in front of the horrified residents. Before they had time to do any more damage, word came that the 39th Missouri Mounted Infantry was heading their way to intercept the raiders. Anderson met up with another group of raiders and they all rode out to meet the challenge.
First, selecting Henry and several other fast riders, Anderson had them ride out in front while the majority of the raiders waited in an ambush farther down the road. When the two forces met, the Union soldiers fired their carbine rifles at Henry and the other riders as the raider group made a fast retreat. As the Union horsemen gave chase they ran straight into the raiders ambush and were cut down in a hail of gunfire.
Several soldiers tried to surrender but were shot. One soldier knelt in front of Anderson, pleading for his life but the guerrilla leader pulled his sword and decapitated the man.
Suddenly one of the Union soldiers rode off and Henry took off after the man. His horse was faster and soon caught up to the fleeing soldier. The rider was in shock as Henry rode next to him for a few seconds before calmly pulling out his revolver and shooting the man in the face. As the soldier fell out of the saddle and to the ground, Henry reached out and grabbed the reins of the other horse and triumphantly led it back to the group.
When he rode up, Henry could see the raiders mutilating the bodies of the dead soldiers---there were over one hundred dead men scattered across the bloody ground. Still sickened by the sight, Henry stayed off at a distance until they had finished.
Later that evening while camped out in the woods, Captain Anderson, after grabbing a cup of coffee from the pot hanging above the fire, approached Henry and sat down next to him.
“You are becoming one of my best men,” he began, “I would make you a lieutenant if you were a little older.”
Stunned and humbled by these words from his hero, Henry could only manage a simple “Thank you.”
“Keep watching and learning,” Anderson continued, “You have the fighting skills---you just need to learn the tactics of warfare and leadership, and you’ll be my lieutenant within a year.”
“Yes, sir,” Henry replied with satisfaction, thrilled that he had proven himself in such a short time, and that his captain had noticed. “Where are we heading next?”
“West, towards Richmond. There are reports of a Union unit over there.”
The two men sat quietly next to the fire, enjoying the company and camaraderie of their association. Most of the group was sleeping, worn out from the days of hard riding and fighting. The plan was to rest for a few days, and then head out to continue taking the fight to the enemy.
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