Whipple served as Paymaster-General of the United States Army from 1908 to 1912 and attained the rank of brigadier general.

[1] He performed paymaster duties throughout the western United States, including postings during the American Indian Wars and assignment to Saint Paul, Minnesota from 1894 to 1898.

[1][3] In May 1884, Whipple was carrying a $30,000 payroll (over $1 million in 2025) to Fort Buford with a sergeant as guard when seven masked men attempted to rob them near Glendive, Montana.

[4] The sergeant was killed and the driver of the stagecoach in which they rode was wounded, but Whipple escaped with the money and hid in some nearby brush.

[5] Whipple was active in Freemasonry; in addition to life membership in Fairibault's lodge, he also belonged to Fairibault's lodge of Royal Arch Masonry, the Washington, D.C. commandery of the Knights Templar, and Washington, D.C.'s Almas Temple of the Shriners.