In 1879, he participated in the Battle of Milk Creek, where he commanded a group of 20 men in a rear-guard action that allowed their column to make an orderly withdrawal from a superior Ute force and establish a defensive position.
[3] On September 21, 1879, Cherry was attached to a column of about 175 soldiers consisting of one infantry and three cavalry companies under the command of Major Thomas T.
[1][5] Cherry and a group of 20 men were ordered to undertake a rear guard action to allow the rest of the command to withdraw and then consolidate a defensive position.
With courage and skill, Cherry conducted a combined retreat and rear guard action over more than 1000 yards, that held the large force of Indians in check, and brought all of his 20 men back to the column.
After the battle, the fourteen non-commissioned officers from the three cavalry companies engaged in the battle (Company E, 3rd Cavalry, and Companies D and F, 5th Cavalry) composed and signed a letter for Cherry, commending his brave and professional actions and "cool, disciplined leadership" in conducting the rear guard action that brought his entire unit back across open ground and under intense fire, to the safety of the entrenchments, with seventeen men out of twenty wounded, and further commending him for his leadership during the siege.
J. Scott Payne, 5th Cavalry, for his quick thinking, training and judgment at the Battle of Milk Creek which kept the command from being first ambushed and later overrun.
[3][6] On May 10, 1881, Cherry was charged with leading a patrol in pursuit of several persons suspected of robbery and the theft of government horses.
On May 11, in the vicinity of White Lake in South Dakota, about 8 miles (13 km) north of the post, he was fatally shot by one of his own soldiers, who was "insane from excessive drink".