The Maltese Cross "Chuck-wagon".
The man on horseback is Sylvane Ferris; the man loading the wagon is Walter Watterson, Roosevelt's teamster and cook.

The encampment where the round-up was to begin furnished a scene of bustle and turmoil. From here and there the heavy four-horse wagons one after another jolted in, the "horse-wranglers" rushing madly to and fro in the endeavor to keep the different saddle bands from mingling. Single riders, in groups of two or three, appeared, each driving his "string." The wagons found their places, the teamsters unharnessed the horses and unpacked the "cook outfit," the foreman sought out the round-up captain, the "riders" sought out their friends. Here there was larking, there there was horse-racing, elsewhere there was "a circus with a pitchin' bronc'," and foot-races and wrestling-matches. A round-up always had more than a little of the character of a county fair. For though the work was hard, and practically continuous for sixteen hours out of the twenty-four, it was full of excitement. The cowboys regarded it largely as sport, and the five weeks they spent at it very much of a holiday.[14]

Roosevelt reported to the captain of the round-up, a man named Osterhaut, saying that he expected to be treated as a common cowhand and wanted to be shown no favors; and the captain took him at his word. He promptly justified his existence. He did not pretend to be a good roper, and his poor eyesight forbade any attempt to "cut" the cattle that bore his brand out of the milling herd; but he "wrestled calves" with the best of them; he rode "the long circle"; he guarded the day-herd and the night-herd and did the odd (and often perilous) jobs of the cowpuncher with the same cool unconcern that characterized the professional cowboy.

"Three-Seven" Bill Jones was on the round-up as foreman of the "Three-Seven Ranch." ("There," as Howard Eaton remarked with enthusiasm, "was a cowboy for your whiskers!") He was a large, grave, taciturn man, capable of almost incredible feats of physical endurance. Dantz overheard him, one day, discussing Roosevelt.

"That four-eyed maverick," remarked "Three-Seven" Bill, "has sand in his craw a-plenty."

As with all other forms of work [Roosevelt wrote years after], so on the round-up, a man of ordinary power, who nevertheless does not shirk things merely because they are disagreeable or irksome, soon earns his place. There were crack riders and ropers, who, just because they felt such overweening pride in their own prowess, were not really very valuable men. Continually on the circles a cow or a calf would get into some thick patch of bulberry bush and refuse to come out; or when it was getting late we would pass some bad lands that would probably not contain cattle, but might; or a steer would turn fighting mad, or a calf grow tired and want to lie down. If in such a case the man steadily persists in doing the unattractive thing, and after two hours of exasperation and harassment does finally get the cow out, and keep her out, of the bulberry bushes, and drives her to the wagon, or finds some animals that have been passed by in the fourth or fifth patch of bad lands he hunts through, or gets the calf up on his saddle and takes it in anyhow, the foreman soon grows to treat him as having his uses and as being an asset of worth in the round-up, even though neither a fancy roper nor a fancy rider.[15]

It was an active life,[16] and Roosevelt had no opportunity to complain of restlessness. Breakfast came at three and dinner at eight or nine or ten in the morning, at the conclusion sometimes of fifty miles of breakneck riding. From ten to one, while the experts were "cutting out the cows," Roosevelt was "on day-herd," as the phrase went, riding slowly round and round the herd, turning back into it any cattle that attempted to escape. In the afternoon he would "ride circle" again, over the hills; and at night, from ten to twelve, he would again be on guard, riding round the cattle, humming some eerie lullaby. It was always the same song that he sang, but what the words were or the melody is a secret that belongs to the wind.

When utterly tired, it was hard to have to get up for one's trick at night-herd [Roosevelt wrote in his "Autobiography">[. Nevertheless on ordinary nights the two hours round the cattle in the still darkness were pleasant. The loneliness, under the vast empty sky, and the silence in which the breathing of the cattle sounded loud, and the alert readiness to meet any emergency which might suddenly arise out of the formless night, all combined to give one a sense of subdued interest.