The frontier both produced and attracted colorful characters like Judge Charles Flandrau, who was born in New York (his father practiced law with Aaron Burr), but, like so many others infected with wanderlust, moved west eventually, to a trading capital on the Minnesota River named Traverse des Sioux, just north of present day St. Peter.
When it became clear that New Ulm was under siege, Flandrau assembled a militia and headed west to the German village on the river, committed to bring aid. Soon enough, he was appointed (or somehow became) the military leader.
Flandrau's men were vastly more willing to fight than they were trained to do it. Hardly anyone had fought an Indian before, and that fact, the Judge insisted, worked against the settlers and their hastily assembled help. "White men, Flandrau once wrote, "fight under a great disadvantage the first time they engage Indians. There is something so fiendish in their yells and terrifying in their appearancfe when it battle, that it takes a great deal of time to overcome the unpleasant sensation it inspires. Then there is a snakelike stealth in all their movements that excites distrust and uncertainty which unsteadies the nerves at first."
It wasn't until Saturday morning that the Dakota, led by Little Crow himself, decided once more to try to take the city. They expected little resistance. By that time, the place had become overrun with refugees, but they'd also gained some fighters, other volunteers who were able to sneak into the city, even though most of the countryside was full of marauding Dakota warriors. Little Crow wasn't going to walk over New Ulm.
His plan of attack included a diversion, which Flandrau fell for, sending 75 of his men out to determine just exactly what was going on at Fort Ridgely. Little Crow's men set fires, whose billowing smoke was meant to trigger that kind of response; but they were pure subterfuge.
Mid-morning, the Dakota fighting force formed a huge line to the north of the settlement, visible to all within the barracaded section of the town the settlers had cordoned off. To counter the imminent attack, Flandrau ordered a significant number of his fighting men to go out from the fortified area and into the houses on the perimeter of the village to try to stop Little Crow's men before they get close to the more than a thousand refugees who were cowering in the basement of a couple of New Ulm's larger buildings.
When the braves advanced with a gigantic cavalcade of shrieking, those perimeter fighters lost their cool, just as Flandrau had said. Some say that had the Dakota pursued them, the town could well have been taken, right then and there. Instead, the did whatever pillaging they could in the defenseless buildings just outside the fortifications.
Two things happened that changed the course of things somewhat. First, a gaggle of sharpshooters called the Le Sueur Tigers (named after their village) kept hold of a windmill by blocking entry and simply picking off whatever Dakota warriors attempted to come near. They were equipped with the finest rifles of all of Flandrau's forces. Second, once the retreating settlers realized that the Dakota were otherwise occupied, they fortified their own positions, even burned some of the outlying buildings themselves to keep the goods from getting into Dakota hands.
It was, by any measure, a horrifying battle, in which 60 settlers dropped in the first hour--ten dead, fifty wounded.
A few hours into what developed into a stalemate, Little Crow decided to attempt another charge, this time from the south, up from the river. Once again, Flandrau sent some of his men outside the fortifications and into the houses on the edge of the village. Some of the roughest hand-to-hand fighting took place on the south side of town, and neither side seemed to gain significant advantage. Death and dying was occuring all around.
Little Crow grew worried. Nightfall would come soon enough, and his people hated fighting at night against an enemy they couldn't see. He assembled sixty of his men to make another charge at the barricades on Main Street.
People advised Flandrau that they'd be powerless against yet another front and urged the whole town to move into a stand of trees. Flandrau thought such a move would be disastrous, and determined that the best defense might be an attack they'd perpetuate themselves. "Get me forty or fifty handpicked volunteers and help me lead them, and we will drive the enemy out of the lower town and die trying," he told his men.
When the men assembled, he told them that going after the band of Dakota in the trees would be their last hope. So they did. Like the Dakota, that band of brave men left the barricades of the village, rifles in hand, screaming and yelling. Once again, fighting raged, but this time the settlers were clearly a match for Little Crow's warriors. When it became clear that his fighting force was probably too far away from the village and in danger of being cut off, Flandrau ordered his men to burn all the houses on the south side of town so there'd be no cover for the Dakota.
The settlers had successfully warded off the very best that Little Crow could throw at them. Thirty-two settlers died, 60 were wounded, and most all of New Ulm, Minnesota was burning. Almost 200 houses had been torched.
What he'd expected from the very first council meeting, the council when he told all chiefs who wanted war that nothing they could do could defeat the waves of white people who would come to defend their own, had become a reality. The war was lost. It wasn't over, but Little Crow had to know that his failure to take Ft. Ridgely--and his failure to take New Ulm--despite his own overwhelming numbers--did not bode well for the Dakota.