While he was talking Joe Gillespie galloped up on Billy Mack, still leading his fresh horse Billy Shafer. To Middleton's astonishment, the fat man was in fine shape and in good spirits and said he would be first in Chicago. The
, which was now carrying news of the race on its front page, said, "Many practical horsemen who saw his mounts share his opinion." Before Middleton had grasped the fact that Gillespie was barely behind him (and with a fresh horse) he had another shock: Rattlesnake Stephens rode up. But there was worse news for the outlaw. Only an hour and a half behind the leader, John Berry arrived at the river at 9 o'clock.
Middleton never got over his astonishment, chagrin and hurt pride. Disregarding outlaw ethics, he whined, complained and charged everyone with trickery. Early next morning Gillespie and Stephens started ahead of him. Before Middleton was under way Berry crossed the river and hurried on into Iowa, willing now to ride ahead of Middleton. Forty miles from Sioux City, Rattlesnake Stephens had to leave his horse Nick. He tried to keep up with Gillespie, with only one mount, General Grant, and did so for a considerable distance: Gillespie and Stephens both checked into the control point at the little town of Galva, Iowa, at 6:45 on the morning of June 21. Berry was exactly one hour behind them. All rested there briefly, Berry leaving 10 minutes ahead of the others. In the 66 miles to Fort Dodge, Stephens passed Berry, to arrive 20 minutes earlier.
Torrential rains had started. Berry was again nursing his horses, traveling more slowly but keeping up by taking shorter stops at night. Between Fort Dodge and Cedar Falls—99 miles—Berry again got the lead, but they were all close together. As they approached Cedar Falls, Stephens and Gillespie both passed him, arriving half an hour earlier. Berry continued to ride another three hours, bedding down at about 10 that night.
The race was now nationwide news. The
reported that Middleton, the best known of the racers, was hopelessly in last place. There was a curious and unexplained fear that foul play would stop Berry. The Tribune reported that his horses were guarded at every stop: "The greatest care was taken to keep the crowd away from the animals, and there is a rumor current that an attempt will be made to poison them." Another Chicago paper sent a reporter to Waterloo, Iowa to accompany the lead rider on a bicycle. But local wags spoiled this bit of journalistic enterprise. A weary rider on a jaded nag posed as a racer and was whisked off by the reporter to a hotel for dinner. He filled the reporter with imaginary tales of his exploits while the real racers passed through town.
Joe Gillespie had stuck with Rattlesnake Stephens ever since leaving Rushville. Now that Stephens had only one horse, Gillespie relaxed. Coming into the town of Manchester, Iowa, 43 miles before Dubuque, he was startled and pleased by the sound of music in the streets and found himself riding into a circus parade. A picturesque character, and now a popular favorite, Gillespie was persuaded to join the parade. As he believed himself safely ahead, he then went to the circus, where he entertained the crowd by riding a trick mule. He then resumed his solitary ride through the checkcrboarded farm country.
But both Berry and Rattlesnake had passed him. Berry crossed the Mississippi River bridge at Dubuque, nearly 800 miles from Chadron, at 12:30 Sunday afternoon, June 25. Rattlesnake crossed at 2:30, Gillespie 20 minutes later. However, this was Rattlesnake's last effort; his only horse, General Grant, was playing out, and now he fell back.
Berry did not know where the others were. He was no longer eating, partly because of the time required, partly to keep down every ounce of weight. New rainstorms struck, and Joe Gillespie, who had no coat, began walking, tying his horses together and leading them. Somewhere around Stockton, Ill., about 40 miles toward Chicago from Dubuque, Berry decided to ride straight through. He reached Freeport, Ill. at 7:20 in the morning, Gillespie coming in at 9:45. Unexpectedly, one of the South Dakota boys, Charley Smith, rode up with two fine mounts, Dynamite and Red Wing, just as Gillespie was leaving at 11:30, and left with him.
Berry rode the 68 miles to De Kalb in 12 hours and 20 minutes. He left there on Poison at 10:50 in the morning, an hour ahead of Gillespie and Smith, in darkness and rain so heavy he could not see the road. Humane society officials were now riding in buggies, accompanying each racer. Berry stayed close to his escort. Gillespie and Smith, however, left De Kalb suddenly, and when the agents assigned to them discovered this and tried to leave also, they found it impossible to hire carriages, and Gillespie and Smith went on without surveillance.
Berry did not stop for feed and water all night. At 7 in the morning he saw the smoke of Chicago and began to worry about the effect that stone roads would have on his horse's feet. The morning grew hot, and at suburban Hey-wood he stopped and gave Poison a spoonful of water. He finally entered the city on Madison Street, which was already becoming crowded with morning traffic. At California Avenue he turned into John Boulevard, asking his way of bystanders. Berry's jeans were mud-covered, his features were red and swollen and he was barely able to hold up his head. His eves were puffed and red from exposure. People stared at him with their mouths open and waved him on. He hit Ashland Avenue and then 22nd Street, after which he reached Michigan Avenue and easily went on to the fair grounds.
A tremendous crowd filled the street in front of the entrance to Buffalo Bill's Wild West Show. Traffic was stopped. A small boy atop a telegraph pole saw the lone rider approaching and let out a yell. A mighty cheer rose from the crowd as Berry jogged up at exactly 9:30 in the morning.