When Quantrell's small command of twenty men was surrounded at night by a large Federal force, while asleep in the Tate house, near Santa Fe, Jackson county, Missouri, in March 1862, Shepherd was with the Guerrillas there, and was selected to guard one of the doors of the house. The conflict which ensued was terrible. After some minutes' fighting, and when the house had been fired, the Federals desired a parley with a view of inducing the Guerrillas to surrender. Shepherd commanded the men who defended the lower rooms of the house. He asked for twenty minutes time. It could not be granted. For ten minutes. No. For five minutes then. No, if the Guerrillas did not yield within one minute, not a man of them should escape, was the ultimatum of the Federal officer. "Then count sixty," exclaimed Shepherd, "and take the consequences." The fight was renewed. That house had become a pandemonium. In it were such men as Cole Younger, Stephen Shores, John Jarrette, James Little, Hoy, Haller, and others. The Federal commander permitted Major Tate and his family to leave the house. Then the fighting was resumed more fiercely than before. The building was on fire. It was manifest that the Guerrillas would be forced to evacuate their fortress. It was resolved to break through the Federal line. Quantrell led the desperate charge, followed by George Shepherd, Jarrette, Younger, Toler, Little, Hoy and others. Seventeen men made the attempt, and succeeded in making their escape. Three had surrendered before the attempt was made. Once, in the spring of 1862, George Shepherd, Cole Younger and Oliver Shepherd were surrounded at the house of John Shepherd, in Jackson county. Their peril was imminent. The Federal force numbered ten to their one. Cole Younger was about to lead a desperate sortie, when Martin Shepherd, Scott, Little and John Coger came up and attacked the Federals in the rear. The diversion enabled the Shepherds and Younger to escape from the house.