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"Dr. Jones, what you look at?"
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"Who's he talkin' about? We gotta kill someone?"

Bobby was a blond-haired thin Irish man who part of Connely's group of Blueshirts, members of a right-wing pro-fascist paramilitary political organization in Ireland, which were in league with the Nazi Dieterhoffmann.

In March 1945, Bobby, along with Pete, and another member of the group had assembled at Connely's Inn, when Connely used a radio to contact Dieterhoffmann about the activities of one of the guests, Indiana Jones. When Connely received word to kill Jones, the three thugs tried to get him in his room, but Jones escaped with help from his assistant, Brendan O'Neal and a picture of Jesus Christ. Switching to chase Jones by car, Bobby drove a car, while his partner shot at O'Neal's fleeing vehicle. After Jones and O'Neal escaped on foot when their car was destroyed, Bobby suggested to turn the cars around when their target was spotted on a horse-drawn cart. As Jones and O'Neal neared the ferry, Jones began throwing bags off the cart, which Bobby attempted to dodge. While avoiding the sacks, he crashed into a construction pit. His partner in charge, and Pete, who drove another car, continued the chase on foot without Bobby.

Several days later, Bobby sat on the stairs at Connely's Inn when the Blueshirts met up with Dieterhoffman, Kurt, Seigfried, and the other Nazis who had arrived to retrieve the Spear of Longinus. While Dieterhoffmann argued with his hostage, Rebecca Stein, Jones returned to the inn, slipped in from upstairs, and held a knife to Bobby on the stairs as his own hostage to trade for Rebecca. Not concerned about Bobby, Dieterhoffmann let Jones know he could kill Bobby if he liked. Connely disagreed with losing one of his men and Dieterhoffmann revealed that he cared nothing for Connely's cause, and ordered Kurt to get Jones. Jones pushed Bobby down the stairs at the burly Nazi, who then grabbed him and threw him off the side of the staircase to get towards his target. Bobby's head hit the ground first, killing him. With Bobby down, Pete attacked Kurt, who punched him out. Enraged over Bobby's death, Connely hit Kurt over the head with a stick, but then Dieterhoffmann shot Connely. In the confusion, Jones and Rebecca Stein escaped with Seigfried's part of the spear.