Ike is believed to have served with the 27th Virginia Cavalry Battalion (a.k.a. 27th Battalion Partisan Rangers) during the early part of the American Civil War (1861 - 1865), and then transferred to Quantrill’s Partisan Rangers in the latter stage, probably in the company of his uncle, Lt. George W. Shepherd. Ike was wounded in 1863 at Widow Moore's place on the road between Independence and Harrisonville.
John M. Flannery also rode with Quantrill’s Raiders, and Sinclair Flannery rode with Todd’s Raiders. Led by Captain William Clarke Quantrill, the guerrillas roamed Missouri and Kansas, raiding farms and villages sympathetic to the Union. They were hailed as heroes in the South and condemned as outlaws by the Union (who operated similar raiding units). They later extended their looting expeditions into Kentucky, and were eventually defeated there by a small force of Union soldiers in 1865.
After the war, Ike joined Jesse James and rode with the James-Younger Gang, participating in a number of train and bank robberies. He was recognised at a robbery and a warrant was issued for his arrest.
Ike was killed near Glasgow, Missouri, by Jesse James and gang-member Jim Anderson (brother of "Bloody Bill" Anderson) for his inheritance of several thousand dollars. His uncle swore to avenge his murder; tracked Jim Anderson down to Texas and slit his throat on the lawn of the state capitol building in Austin on 10th May 1867. His uncle is also reported to have wounded Jesse James at Short Creek, near Joplin, Missouri.
[his portrait is sought]