Unlike Luther Kelly’s initial meeting with Nelson Miles, we don’t know the time and place of Kelly’s first meeting with Theodore Roosevelt, though it would in all likelihood have to have been between 1884, which marked the first time TR came West, and Kelly’s departure from Colorado in 1890.
In 1880 Luther Kelly moved into western Colorado where he took up ranching and farming along the then Grand River (today’s Colorado River) In 1885,Kelly married one Alice May Morrison (called May), and we might imagine that the couple lived an idyllic sort of life for the next five years. Kelly’s memoirs, and what correspondence has survived, do not go into great detail about this period of Kelly’s life, but it would be reasonable to propose that now and then he left May and his ranch behind to guide hunting expeditions, that on one or more occasions may well have included Theodore Roosevelt. Although the ranch life may have been peaceful enough we sense that it was not all that profitable and guiding these hunting forays would have helped the financial picture.
Whatever the circumstances of that first meeting, a bond of sorts did develop between Kelly and Roosevelt, and clearly it was something more than a casual sort of relationship. In 1903, while conducting a successful defense of the American provincial building in Mindanao, Philippines against bandits, Kelly received a warm letter of congratulations from TR. And later, when Kelly was seeking a permanent Army position, following his Philippine service, TR wrote to the Secretary of War on his [Kelly’s] behalf, saying that he had known Kelly “in the early days of the West”. Gestures such as these suggest that Luther Kelly and Theodore Roosevelt enjoyed something beyond a casual friendship.
Roosevelt had a fondness for men who appreciated the wilderness; who exemplified the rugged outdoor life, but who also enjoyed books and fine conversation, and Luther Kelly fit that mold to a t. TR’s second term as president saw the creation of what came to known as his “tennis cabinet”, which was composed of perhaps thirty or forty men with whom TR hiked, rode, swam, or played tennis. The activity mattered only to the extent that it was physically demanding. Luther Kelly was a member in good standing.
In the closing years of his life, Luther Kelly devoted his time to writing his memoirs and corresponding with old friends, including Theodore Roosevelt. Kelly had participated in two expeditions to Alaska at the turn of the century; he had been mightily impressed with the stunning vistas, the glaciers, the exuberance that filled one’s being, and he made it a point to encourage TR to visit Alaska, but the ex-president having barely survived a journey down the Amazon River, found an Alaska adventure beyond his reach.