Rule number one in The Bond Villain Guidebook is that unnecessarily elaborate murder plots are bound to fail. (This rule may be restated as Scott's Razor: When you want someone dead, just grab a gun and shoot them.) Rule number two is do not reveal your evil plan. Rule number three is if you try to kill someone make sure they're dead before walking away. Rule number four is make your prison escape proof. All Bond villains violate at least two of these rules and it leads to their downfall. Silva defies all logic by creating the most insanely elaborate murder plot in movie history and it eventually (sorta) succeeds.
Part one of Silva brilliant plan involves stealing a list of every spy in the world. Not for its enormous economic value or an ideological "kill all spies" purpose. But because it's a really embarrassing thing to lose and it will get M in trouble with the higher ups. Eventually, it gets M dragged before a Parliamentary panel despite the fact that we are assured that the government wants to keep this quiet because this list shouldn't exist and they really don't want anyone knowing they lost it.
Part two begins while M is being chastised for the whole lost list thing. During which time, Silva hacks into MI6 and sets off a bomb in M's office making sure to check her calender first so that he won't disturb her busy day by blowing her up. (Hi, SAM.) That's right. Silva's entire purpose is to kill this woman and he plants a bomb in her highly secure office and intentionally sets it off when she's not there. This is where Scott Evil needed to intervene (at 1:50 in this video).
Anyway, his part two goal of move MI6 to the tunnels of London is accomplished and he begins part three of his plan, which is to get himself captured by Bond and brought to the shinny, new and very rapidly built MI6 HQ. Silva once again hacks into the MI6 mainframe to begin his escape which was "years in the planning." He also takes the opportunity here to reveal his evil plan. His escape involves repeated split second timing including dropping a subway train on Bond's head. (The London tube time tables would fill Mussolini with envy.)
Part four of Silva's plan takes place at M's Parliamentary hearing which we were told earlier wouldn't happen and is going on during Silva's escape. In this most brilliant portion of his plan, Silva gets some guys and some guns and breaks into another high security building to shoot M. Yes, years of planning to get them both in the same room in the most improbable fashion, theft of super top secret information from an intelligence agency, twice breaching physical and electronic security of and a daring escape from said intelligence agency (MI6 needs a serious security review.), and another breach of another secured facility all just to shoot someone in the face. And when the critical moment comes, Silva hesitates allowing M to escape.
Skyfall is a classic example of a Planning Paradox. Silva's plan is too intricate to work without detailed advanced planning but relies on too many intricate details to have planned in advance. You can't drop a train on someone's head as a witty retort without knowing exactly when the train will be there but the position of the train is unknowable in that detail. In a less extreme example, Silva is not in control of the hearing schedule or the exact time of his escape, but both must be simultaneous for his plan to work. Silva must either be a psychic with advanced knowledge of the future or a wizard conjuring whatever he needs for the next step of his plan.
From this point on, Silva goes improvisational. Improvisation which includes hiring a bunch of guys with guns and renting a helicopter with a kick-ass sound system. (Where does he get the funding?) Unsurprisingly, this more direct approach actually succeeds in killing M which just goes to show you that the simplest plans are usually the best.
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