Riley Aldrin Shepard was a cadet at Starfleet Academy in the 2370s. His Starfleet Service number was C95304699427 and he was a member of the elite Red Squad. In 2372, he was in his third year and had a specialty in tactical operations. (DS9: "Paradise Lost")
In that year, he helped to disable the global power distribution center in Lisbon, allowing Admiral Leyton to launch a coup attempt. It was after he talked to Shepard that Benjamin Sisko was able to expose Leyton's coup attempt. After Leyton found out the cadet had spoken to Sisko, and that he wanted to speak to him again, Shepard and the other members of Red Squad were sent on a training exercise. (DS9: "Paradise Lost")
In 2373, Red Squad were assigned to crew the USS Valiant, on a training mission to travel around the Federation. Following the outbreak of the Dominion War, the Valiant found itself trapped behind enemy lines. When the commanding officers were killed, Cadet Tim Watters assumed command, and kept the ship behind enemy lines.
Shepard served as helmsman and was awarded a provisional rank of lieutenant by the overzealous Watters, who ordered the crew to continue missions in Dominion space. Shepard and most of Red Squad were killed when the Valiant engaged a powerful Jem'Hadar battleship prototype and was destroyed. (DS9: "Valiant")
|Members of Red Squad|
|Tim Watters • Karen Farris • Riley Shepard • Dorian Collins • Parton|
|USS Valiant personnel|
The script for "Paradise Lost" describes Shepard as "a confident, nineteen- to twenty-year-old Starfleet cadet."