Several years earlier, Eddie and his best friend Milo Walker owned a restaurant in Brantford together, which was named "Milo and Eddie's", however, after 15 years, Milo decided he was getting too old to be working the same old routine and chose to retire while he still could, and sold the restaurant to a new owner, Nora Shepherd, which greatly angered Eddie and led to the loss of their friendship.
Years later, while recovering from hip surgery, Eddie was staying at the house of his grandson, Spencer Gilpin, who had arrived home for the holidays from college, and the two shared Spencer's old room together. The next day, Milo visited, wanting to reconcile and restore their friendship, but Eddie was still too angry about being forced into an unwanted early retirement and wanted nothing to do with him. A little while later, Fridge, Bethany, and Martha arrived at the house searching for Spencer.
Upon discovering that Spencer had gone back into "JUMANJI" via the video game, the three decided to go in after him, but the apparently malfunctioning system also sucked in Eddie and Milo, leaving Bethany behind. Eddie was forcefully placed in Spencer’s former avatar: Dr. Smolder Bravestone. However, unlike his grandson, Eddie's elderly stubbornness and impulsive recklessness with his newfound strength got the team into countless trouble, eventually costing them each two of their three lives. He also constantly spams Bravestone's "Smoldering Intensity" skill at random moments throughout the game.
During the game, Eddie still refuses Milo's attempts to make up with him, but as they continue along, he eventually reconciles with his old friend, who tells Eddie that the reason he desires to rebuild their friendship is that he has some unspecified terminal illness, and not a lot of time left to live.
After finding Spencer, they stumble upon a pool of water that allows them to switch avatars, Eddie is placed into Spencer's avatar of Ming Fleetfoot. He uses the thief skills to aid them in retrieving the jewel, and rides Milo, who had been placed into Bethany's avatar of a Horse named Cyclone, who has the hidden ability to fly, in order to hold the Falcon Jewel up to the sun and win the game.
After winning, Milo reveals that he has decided to stay behind in "JUMANJI" and protect it, now that he has his wings. Eddie and Milo finally mend their broken bond and share a heartfelt goodbye as Milo rides off. Upon returning to the real world, Eddie and Spencer bond over a video game, and Spencer later takes him to his old restaurant to meet up with Spencer's friends, during which Eddie talks with Nora Shepherd and tries to use the Smoldering Intensity look to flirt with her.
Although Spencer's father has not appeared in the films, Eddie is more likely his father considering that Eddie and Spencer share the same surname, which would make Mrs. Gilpin his daughter-in-law.