President George W. Bush approved the execution of an Army private, the first time in over a half-century that a president has affirmed a death sentence for a member of the U.S. military.

With his signature from the Oval Office, Bush said yes Monday to the military’s request to execute Ronald A. Gray, the White House confirmed. Gray had been convicted in connection with a spree of four murders and eight rapes in the Fayetteville, North Carolina, area over eight months in the late 1980s while stationed at Fort Bragg.