He once owned a watch that was passed down to Christian and then to Jack, on his wedding day. Christian explained that he didn't like the watch because Ray had told him on his wedding day of his disapproval of Margo.("The Watch")
One day before Jack boarded Ajira Airways Flight 316, he visited Ray at his retirement home. Ray had just made the latest in a series of attempts to escape the home. Ray declared his dislike of the facility and said he would one day escape, claiming, "They won't ever find me, either." They discussed Kate, whom Jack had at some point introduced to his grandfather. Helping Ray unpack his suitcase, Jack found a pair of shoes which belonged to Christian. After Christian's death, his wife Margo had given some of Christian's belongings to his father Ray, including these shoes. Jack asked to take the shoes and he later placed them on Locke's corpse. ("316")
In the casting call, Ray was named "Hal", and described as "70s, Caucasian. Successful, handsome and charming rogue with a twinkle in his eye. A guy who can still fight the establishment and win." 
- For fan theories about these unanswered questions, see: Ray Shephard/Theories
- Why did he believe that Margo was the "wrong choice" for his son to marry?
- Why is he always trying to escape his retirement home?
- Where does he think he will escape to that no one will find him?