On the way to Baker Island his plane (Condor 9) was hit by flak that nearly destroyed the plane's engines. An explosion in the cockpit killed the pilot and almost caused the plane to crash into the water. But another paratrooper, Probst Wyatt managed to steady the plane long enough for Fergus Reid and BJ to jump onboard.
When the plane crashed off the coast of Baker Island, Benson regrouped with his team, and they managed to get beyond the German trenchline and beyond the Stomper, after reaching the entrance to the compound, Fergus told Benson, B.J. and Gates to climb up the wall to open the gates. While climbing, Nazi soldiers fired at the trio, a bullet later grazed Benson in the neck and after managing to kill the Nazi who shot him, he falls off of the wall to his death.