Grandpa Portman’s death is the turning point that transforms Jacob Portman’s family history from a collection of troubling stories into a mystery he must pursue. Found near death in the Florida woods, he gives Jacob a chain of precise instructions—to go to an island, find a bird in a loop, and look beyond an old man’s grave on September 3, 1940. His death leaves Jacob with a task but not an explanation; a creature glimpsed immediately afterward makes the danger behind his words seem real.

Discovery in the Woods

Jacob searches the underbrush with a flashlight, convinced his grandfather is somewhere nearby. When he finds a narrow track of flattened palmettos, he follows it past dark stains on the leaves. The trail opens onto the place where Grandpa Portman lies, and Jacob initially believes he is dead. He is still breathing, however, and remains barely conscious.

Jacob calls for Ricky, who is elsewhere in the yard, then takes a brass letter opener from his grandfather’s hand. He cannot move him without causing pain, so he stays beside him and waits. The scene makes the limits of Jacob’s understanding plain: he can recognize that his grandfather is in grave danger, but he cannot yet identify what has happened or what is in the woods.

The Last Instructions

As Grandpa Portman fades in and out of lucidity, he tells Jacob to go to the island, insisting that it is safer there. Jacob initially takes this warning as another expression of his grandfather’s familiar paranoia and reassures him that they are safe. When asked what happened, Grandpa Portman does not answer with an explanation. Instead, he returns to the island and asks Jacob to promise.

He then admits that he had thought he could protect Jacob and should have told him the truth earlier. With little time left, he gives the directions that shape Jacob’s next steps: find the bird in the loop, on the other side of the old man’s grave, on September 3, 1940. He also tells Jacob to look to Emerson—the letter—and to tell them what happened. These instructions link a place, an apparent time loop, a date, and a written source, but Grandpa Portman dies without making their meaning clear.

Death and Immediate Aftermath

Jacob tells his grandfather that he loves him. Grandpa Portman then seems to withdraw from the conversation, his gaze passing beyond Jacob toward the sky. Ricky arrives moments later, sees the limp figure in Jacob’s arms, and reacts with alarm. His questions about finding a pulse, calling the police, and whether anything was seen in the woods contrast with Jacob’s sudden sense that something is nearby.

Jacob raises the failing flashlight toward the underbrush and sees a creature with a distorted humanlike face and a mouth from which long, eel-like tongues protrude. It turns and disappears into the trees. Ricky fires his .22 in the direction of the movement, but he has not seen what Jacob saw. Jacob remains unable to explain it and blacks out; the glimpse therefore connects his grandfather’s death to a threat that remains invisible to his companion, without yet revealing who or what caused the fatal encounter.

The Island’s Public History

Jacob’s later arrival on Cairnholm gives the island in Grandpa Portman’s instructions a history, though not at first the one Jacob expects. At the museum, Jacob encounters the preserved body known locally as the Old Man and archaeologically as Cairnholm Man. The curator identifies him as more than 2,700 years old, although he was sixteen when he died; his body was preserved beneath the island’s bog, where oxygen and bacteria could not exist. The displayed remains provide one concrete counterpart to the cryptic reference to an old man’s grave, but the evidence does not establish that they are the same person Grandpa Portman meant.

The island’s accounts also establish that its former children’s home was destroyed during the Second World War. A German air raid struck Cairnholm, which had an anti-aircraft gun battery; a bomb went off course and hit the home. Oggie recalls that the raid took place on September 3, 1940, the exact date Grandpa Portman gave Jacob. He says that townspeople were not killed, while the gun crew and the children at the home died. The date thus connects the private last words Jacob could not understand to a publicly remembered wartime disaster.

Departure and Retrospective Meaning

Oggie remembers one survivor leaving after the bombing. In shock, the young man spoke only to ask when the next boat to the mainland would depart, then said he wanted to take up arms against those who had murdered his people. Jacob recognizes the man as his grandfather, revealing that Grandpa Portman had once been among the children at the home and had left Cairnholm after the raid. The testimony does not explain every part of his final message, but it places his past on the island and the date he named within the history of the bombing.

The later accounts recast the death scene without erasing its uncertainties. Jacob’s first response had been to treat the island warning as an old fear; the repeated date and the account of his grandfather’s departure show that the warning points toward a real, specific history. The preserved Cairnholm Man, the ruined children’s home, and Oggie’s recollection are separate fragments of the island’s past, not a complete explanation of the attack in the woods. Grandpa Portman’s death leaves Jacob to assemble those fragments, and his final words become the means by which a family loss opens onto the book’s larger mystery.