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So I just watched Terminator: Genisys. Then I watched videos explaining all the timelines. The explanations were all well and good and fairly similar across the websites.

But this is what I don’t get. A Terminator is sent back in time to kill Sarah or John Connor. The only reason given in the movie and on the websites is that by killing either of them, John would not be able to lead the resistance against the machines.

While I can easily understand Skynet does not want John to lead the resistance, it doesn’t guarantee success. Yes, you stop John from leading the resistance, but that doesn’t mean someone else would not rise to the role of leader and stop Skynet. Given the power of time travel, it would seem to me there are better choices in guaranteeing Skynet's survival.

Why is Skynet utterly obsessed with killing John Connor?

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    Then Skynet would send another Terminator to kill that new guy and so on an so forth. – bobbyalex Aug 18 '15 at 5:27
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    John's mother told him the best ways to fight Terminators and a bunch of other important Skynet stuff. John told his troops all these things, which in turn gave the resistance a much better chance against Skynet. No one else knew what John and Sarah knew. – Daft Aug 18 '15 at 7:57
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    “it would seem to me there are better choices in guaranteeing Skynet's survival” — Such as? – Paul D. Waite Aug 18 '15 at 9:50
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    I think you may be underestimating John's influence over the development and leadership of the Resistance. – Valorum Aug 18 '15 at 11:35
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    Skynet did do more than just hunt for the Connors; it actively built a new timeline wherein it was more in control of its own future (re 'Genisys Program'); it certainly didn't put all of it's eggs in the one basket. – Möoz Nov 8 '15 at 20:11
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The following dialogue from the original film (The Terminator, dir. James Cameron, 1984) made it clear the time travel plan was a desperate, last-ditch move on the part of Skynet:

Dr. Peter Silberman: Why this elaborate scheme with the Terminator?

Kyle Reese: It had no choice. Their defense grid was smashed. We'd won. Taking out Connor then would make no difference. Skynet had to wipe out his entire existence!

Dr. Peter Silberman: Is that when you captured the lab complex and found the, uh, what was it called... the time displacement equipment?

Kyle Reese: That's right. The Terminator had already gone through. Connor sent me to intercept him and they blew the whole place.

Dr. Peter Silberman: Well, how are you supposed to get back?

Kyle Reese: I can't. Nobody goes home. Nobody else comes through. It's just him - and me.

The plan was not at all guaranteed to succeed, but it was the last remaining option. The above dialogue implies Skynet had very little time between the time displacement equipment becoming operational, and the final victory of the human resistance, so it would have had to move quickly.

It's also worth bearing in mind that Skynet knew very little about the world before the nuclear war:

Kyle Reese: Most of the records were lost in the war. Skynet knew almost nothing about Connor's mother. Her full name, where she lived. They just knew the city. The Terminator was just being systematic.

(Source as above)

So Skynet lacked the information for some sort of clever scheme to manipulate the past; all it had the time and knowledge to implement was the very simple plan of trying to kill John Connor before he was born.

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