3. James T. Kirk (Star Trek Generations)
Given that there are a considerable number of years between the timeline of the original Star Trek series and the Next Generation crew, you kind of expected that Kirk would no longer be alive, but when it turns out he is in fact alive and well in the Nexus, it allows him to team up with Picard and kick some ass. At least that's what we thought would happen, the team up lasts all of ten minutes before Kirk receives an unceremonious after falling off a bridge. It is such a stupid death, why did he even need to die at all? Scotty is alive and well in TNG timeline so why can't Kirk live out his days in the 24th century? Or maybe he could have returned to the Nexus, but there was surely no need to kill off such a legend?