Emmett Albright was prevailed upon to enter. He couldn't get out of it, since the city fathers were grimly announcing that the whole thing was his idea.
These spectacular figures overshadowed the genuine cow-punchers in the race—Dave Douglas, a teen-age rider, old Joe Gillespie, Joe Campbell from Denver and two South Dakota boys, George Jones and Charley Smith.
Almost as the horses were lining up, John Berry entered the race. Berry came about as close to being the classic figure of the western good man—opposed to the western bad-man—as was possible for a creature of flesh and blood. He was slight, soft-spoken, modest, hard-working, intelligent and kindly. His reputation as a hero stemmed from the fact that he had kept the mail stage running to Fort Niobrara during the Indian wars, which lasted until 1891 in the country through which he drove the stage. Since he had no suitable mounts of his own, he rode the horses of Jack Hale, a South Dakota rancher: Sandy, a bay gelding, and Poison, a magnificent 5-year-old stallion that was a mixture of Kentucky Thoroughbred and western range stock.
Doc Middleton and his cronies immediately withdrew from the race. They refused to ride if Berry rode. They said he was disqualified because he had helped the race committee plan the route. The start was delayed all day. Berry finally agreed to forfeit the prize if the judges ruled against him, in order to get the race started. So Doc Middleton came back in, but with the conspicuous bad feeling of a notoriously dangerous man.
Early in the morning of the second day of the race Joe Gillespie heaved his 185 pounds on Billy Mack, his chestnut gelding and, leading his gray, Billy Shafer, headed into the hills east of Rushville. The route ran due east through the Sand Hills, a desolate extension of the Dakota Badlands, to the first control point at Long Pine. In wet weather travel through the Sand Hills wasn't so bad, for the roads and trails packed hard, but in the summer the dry sand dragged heavily. The hills were like desert sand dunes, but thinly covered with grass. They shifted constantly under the wind from the Rockies. Big bare sandy hollows, known as blowouts, formed between the hills. The whole terrain was an enormous sponge, soaking up rain and rivers and releasing the water in isolated pockets and valleys.
In midmorning Doc Middleton and Rattlesnake Stephens, riding hard, passed Gillespie, who, however, kept them in sight. Middleton was riding as if evading the law, which in fact he had often done in the Sand Hills. He had a hideout almost in the middle of them, where the famous Sand Hills bird sanctuary is now located. Middleton's strategy was simple: he was going to ride the others out at the start of the race, relying on his private knowledge of this unknown region. He was willing to burn out one of his horses, since he planned to be so far ahead he could get through the easy country of Iowa on Geronimo alone.
Where he stopped on Wednesday night and Thursday night is not recorded. At 4:45 on Friday afternoon he rode into Long Pine—phenomenal time in view of the nature of the country. But Gillespie and Stephens were still keeping up with him. Forty-five minutes later Emmett Albright rode up to the control point. The others were scattered halfway across the Sand Hills, Berry in last place. If anyone knew the Sand Hills better than Middleton, it was Berry. He had been the first homesteader there, a place now called Johnstown, not far from Middleton's hideout. Berry certainly did not try to make speed through the sand. He walked his horses, often walking with them. He never used a whip or a spur. Instead of racing in bad terrain, he used the time to win the confidence of the horses, thus letting strange mounts become thoroughly familiar with him at the start of the race. Beyond the Sand Hills, and before Long Pine, the road entered steep, wild, wooded hills and the fossil-filled canyons around Bone Creek. Here Berry also rode slowly. He was nearly a day behind the leaders.
Middleton was away early on Saturday morning. The headquarters of the Pony Boys had been in nearby Bassett, at the Martin Hotel, and Doc wasn't popular around there. He pounded on through Stuart and Atkinson to O'Neill, the second control point, 59 miles from Long Pine. His strategy seemed to be working: Dave Douglas dropped out of the race at Atkinson; he had worn out one horse trying to catch Middleton in the rough country and wouldn't go on with only one mount.
Beyond O'Neill the road ran over level country, where limitless acres of wild hay were harvested commercially each fall, the old stacks standing like small mountains beside the road. Middleton continued to ride hard, checking in at the third control point, Wausa, 58 miles beyond O'Neill, and driving on toward Coleridge and Sioux City. John Berry registered at O'Neill 13 hours after Middleton.
At Coleridge, Middleton left his horse Jimmy, who had begun to go lame. He started from there at 5 o'clock in the morning, jogged slowly but steadily all day, making four stops to feed Geronimo, and at 7:30 in the evening came to the Missouri River opposite Sioux City, where a large crowd had gathered. As the cheers rose, the outlaw doffed his white sombrero and waved it in triumph. "I am a little tired," he said, "but will get over it with a good night's rest. My horse is in good condition, and I believe I am a winner, even if I have but one horse."