Jesse spent most of his time flying and training or on alert and ready to take to the air at a moment's notice, but there were occasional passes that allowed him an entire day's liberty. He had been an outdoorsman all his life and such liberty was often spent exploring the wilderness areas.

One day, he and a friend had taken a canoe to do some freshwater fishing. They were paddling along when Jesse noticed some blackberry bushes near to the water's edge. They landed the canoe and Jesse wormed his way through a low hanging thicket to pick the coveted blackberries.

He was involved in this pursuit when he sensed a movement above him. Looking up, he was startled to see a full grown Kodiak bear rearing above him. Jesse was armed with only a small 22 caliber revolver stuck into the waistband of his pants and he knew better than to try to take on the beast with such a puny weapon, for a wound would only serve to enrage the bear.

In that instant, he pulled out the gun and fired it straight up into the air, thinking to distract the bear for the instant it took him to scramble back into the canoe and paddle hastily to the safety of deeper water. They did not stop paddling until they were well away from the vicinity.

Jesse and his friend returned a week later to see if there were any blackberries left. They found instead the carcass of the dead bear. A closer examination revealed that the small bullet from Jesse's gun had entered through the bear's open mouth and lodged in his brain, killing him instantly.

Jesse later gave the gun to Thomas and Forrest as a momemnto, but their father commented his disaproval, noting that the seven-shot revolver had six bullets too many.