Sir Richard Grey is the younger half-brother of Edward V, born to Elizabeth Woodville and her first husband, Sir John Grey. He wields influence within the Yorkist court, particularly in the political and administrative oversight of Wales and the bordering English counties. Knighted in 1475, he subsequently served on judicial commissions and as constable of Chester Castle.

By 1483, he shouldered key responsibilities in the household of Edward V, then Prince of Wales, at Ludlow Castle. Following Edward IV's death, he accompanied the young Edward V and their uncle Anthony Woodville on the journey to London for the prince's coronation. Richard, Duke of Gloucester (later Richard III) intercepted them at Stony Stratford. Sir Richard Grey was arrested alongside Anthony Woodville under allegations of conspiring against Gloucester and offering poor counsel to the late king. No trial occurred, and contemporary accounts questioned the charges' validity.

After his arrest, he was first imprisoned at Middleham Castle before transfer to Pontefract Castle. On June 25, 1483, he was executed at Pontefract on Gloucester's orders, alongside Anthony Woodville and Thomas Vaughan. This execution occurred one day before Gloucester's accession as Richard III. Sir Richard Grey was approximately 26 years old at his death. His lands and offices, including the manor of Thorpe Waterville, were redistributed prior to any formal legal deprivation.

Within the narrative, Sir Richard Grey is depicted as Edward V's loyal supporter. He participates in events like a royal hunt orchestrated by Elizabeth Woodville, intended as a trap for Richard III. When the trap fails, Richard III declares Edward V and his brother Richard illegitimate, leading to their imprisonment in the Tower. Sir Richard Grey's role in this sequence underscores his alignment with the Woodville faction against Richard III's ambitions.