A Die Hard prequel comic makes it seem like John McClane should have realized a lot sooner in the original 1988 film that the movie's villains were only pretending to be terrorists to pull off a heist. In 2010 Boom! Studios published an 8-issue limited series called Die Hard: Year One. The Howard Chaykin-Stephen Thomas collaboration tells the story of a younger John McClane more than a decade before the events of the original Die Hard movie. While comic was never able to mirror the success of the film series, it did make enough of an impression on filmmakers for it to be chosen as the basis of the ill-fated sixth Die Hard movie.
The fact that the comic was being going to be adapted for the film series means that it is considered Die Hard canon. Therefore, John McClane in the movie A Good Day to Die Hard should remember what happened in Die Hard: Year One as easily as he remembers what happened in the original movie. The comic adapts the films' unmistakable "day-in-the-life" style to tell its tale. The story begins on July 4, 1976, when McClane is a newly minted member of the New York Police Department who is asked to provide security for the Police Commissioner during a meet and greet onboard the yacht of one of the city's most powerful business executive. Naturally for McClane, the yacht gets commandeered by a bunch of "terrorists" who threaten to blow it up unless their demands are met.
Within a few minutes of hearing the demands of the so-called "terrorists," John McClane points out that they're just pretending to be terrorists to disguise their real motive: money. McClane's theory is initially dismissed by others working with him but ultimately he's proven correct. What is impressive about his analysis of the situation is that he does it with only a year's experience as a cop. To be sure, as he himself says in the comic, it's a combination of his life experiences and police training that informs his crime-fighting expertise. Fast forward to Christmas Day 1988, when the now-veteran police detective John McClane faces another group of fake terrorists who take over Nakatomi Plaza. Based on what is presented in Die Hard: Year One, McClane's training and experience—now deepened by 12 years of taking down criminals on New York's tough streets—should tell him that Hans Gruber and team are not terrorists but criminals. To be sure, identifying Gruber as a criminal rather than a terrorist would have changed a number of story points such as the FBI's helicopter plan.
Interestingly, McClane does not figure out that Gruber and company are criminals until the end of the movie when he sees and overhears them moving stolen bonds. McClane's failure to see them for who they truly are happens despite there being numerous clues to the contrary. Indeed, the clues are much more obvious than those provided in the comic. Additionally, on more than one occasion, McClane corroborates the fact that they are terrorists, such as when he says that he recognized that they have fake IDs that would have been expensive to make. Presumedly these IDs are more expensive than a common criminal could afford.
Naturally, there are a few reasons why an older John McClane might be fooled. For instance, Gruber is a former member of a terrorist group, most of the group are internationals, and they are armed with weapons like rocket launchers, which most criminals would be unable to get. Nevertheless, the time gap between Die Hard: Year One and the original Die Hard is too short for John McClane to have completely lost his senses. Naturally, the expectation is that his abilities in this area would only get better with age, not worse.