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「私はすぐには行動しないだろうと侮っていた」

It seems as though だろう is expressing something that is outside of what I've normally seen it used for (e.g. as a substitute for でしょう to mean "probably")

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    I'm not a veteran/expert (so I might be wrong), but I'm reasonably sure it should be only one question per post -> two questions (that are unrelated) should be two posts. See also: meta.stackexchange.com/questions/222735/… – Sam Apr 19 at 21:24
  • It should indeed be two separate questions. And please add in what you think the translations should be and explain why だろう doesn't meet your expectations. – user3856370 Apr 19 at 21:31
  • Thanks, have fixed it I believe! – Noah Apr 19 at 22:05
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This だろう does have the function of inference, "I suppose" or "probably will ~". The subject of 侮っていた is 私, but the subject of 行動しないだろう can be either 私 or someone else who has been mentioned in the previous context. と is just a quotative particle.

すぐには行動しないだろう。
= すぐには行動しないでしょう。

I think [someone] will not act right away.

私はすぐには行動しないだろうと侮っていた。

I had been under the impression that [they/I] (probably) would not act right away.

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