He had a most charming personality, and his well-bred manner, his elegance of carriage and movement, his lithe and erect figure, and the zest with which he entered into tennis, football, boxing, and running races, together with his courtesy and good humor, made him conspicuous among his classmates.

Roosevelt mentioned him in his account The Rough Riders: When I went down to the camp at San Antonio he was on kitchen duty, and was cooking and washing dishes for one of the New Mexican troops; and he was doing it so well that I had no further doubt as to how he would get on.On July 1, 1898, in the assault on San Juan Hill by the Rough Riders, and while leading K Troop, Kane was wounded in the forearm and arm by Mauser rifle fire.

Kane is one of the Rough Riders featured in the foreground of Frederic Remington's famous painting of the charge on San Juan Hill.

Regular Army officer, San Juan Battle Gatling Gun Commander batter commander and renowned developer of their forward tactical use, John H. Parker, described Captain Woodbury Kane in his book, as follows: Woodbury Kane – social leader, Fortune's favorite, aristocratic, refined, cultured, wealthy, haut ton de haut ton, and sabreur sans peur et sans reproche–how shall I paint him to you as I learned to know him in those dreadful, delightful seventeen days in which we lived only from instant to instant, and every man unconsciously bared his soul to his comrades because he could not help it?

Well groomed; in those days when our bed was a mud-puddle and our canopy the stars, when the music which lulled us to sleep was the hum of the Mauser bullets and the vicious popping of the Remingtons, when water to drink had to be brought at the peril of life for every mouthful, Kane turned up every morning clean-shaved and neatly groomed, shoes duly polished, neat khaki, fitting like a glove and brushed to perfection, nails polished, and hair parted as nicely as if he were dressed by his valet in his New York apartments.

No man was readier to bind a wound or aid a sun-struck soldier in the ranks; none more ready to deny himself a comfort or a luxury to help a more needy comrade.

A grand example to our pessimistic, socialistic friends and cheap demagogues of the sterling worth and noble, chivalric character of a "society man of wealth."

[7]Upon returning to the United States, Captain Kane became a veteran companion of the New York Commandery of the Military Order of Foreign Wars.

Woodbury Kane, Stanley and Richard Mortimer and Belmont Tiffany gave a large sum of money to Roosevelt for those in need.

When he returned home, Kane resumed his social life in Aiken, New York and Newport (Rhode Island) where he became a competitive yachtsman.

[10]Kane died on December 5, 1905, at his apartment at the Algonquin Hotel in New York City from paralysis of the heart after returning from duck hunting in South Carolina, after contracting a cold.