One of the central values of the Agile Manifesto is Responding to change over following a plan. This doesn't mean that it's not agile to make a plan. You should have a plan, but you should realize the limitations of the plan.
Are there any parallels to this in history?
The Soviet Union had 5-year plans. Stalin was quite succesful in industrializing the rural country in a short span of time. But his methods did not work well in the battlefield. In the 2nd world war, the Soviet suffered severe losses in the beginning.
You can plan how to build and manage a factory, because the complexity is limited. But a war is far more complex. You cannot predict what the enemy is going to do. This doesn't mean that you should go to war without a plan. Far from it, you should plan as much as possible, but be prepared to improvize when something unexpected happens. As Dwight D. Eisenhower, a successful American general in World War 2, said: "Plans are nothing; planning is everything."
Building software is also complex. But some managers try to run a software development organization as a factory. They treat their employees like cog-wheels. They think that Employee #1093 can take over the responsibilities of Employee #835 with just some training. Or that 4 programmers can do in 3 months what one programmer can do in 1 year. It doesn't work like that. If software development was so predictable, then robots could do it. But they can't.
I don't like being treated like a cog-wheel. I am not Employee #1093, I am me. I am unique with my own weaknesses and strengths. If I am treated like a replaceable part, I may start to behave like one. Then, I will only do as I'm told, nothing more, nothing less. If nobody listens to my ideas, I will stop thinking creatively, and just do things the way we always did.
Since I don't want to become mediocre, I avoid environments like that. I seek challenging environments where my ideas are heard and I am given responsibility to work as I think is best.
I think that Churchill, the Prime Minister of Great Britain during WW2, was agile too. He was not afraid to change. He said: "To improve is to change; to be perfect is to change often.
He also said, "However beautiful the strategy, you should occasionally look at the results." That sounds like iterative development to me. You make a plan, and then review the results now and then to see how it works. (See more fantastic quotes of Churchill here.)
So how about Hitler? How agile was he? Not agile at all. He had a great vision and a plan that seemed to work very well in the beginning. But as we all know, he failed. I think this is similar to a waterfall project: He was 80% finished with conquering Western Europe, and 75% finished with Eastern Europe. If he had run the war more iteratively, he should have completed Western Europe first, and then started on Eastern Europe. Thank God, he didn't!
What did Hitler and Stalin have in common? Both nazis and communists were rationalists with a strong belief in their own enlightened minds. I dare say that Churchill and Eisenhower had a more humble attitude, accepting that they could not make perfect plans. I would also say that Churchill was empiric in that he wanted to review the results of his plan.
Rationalists think they can plan everything. Empirists believes in experimental evidence. I think that waterfall development is a result of rationalist thinking, but it doesn't work well, because our minds are limited. We cannot predict everything, but we are capable of planning to a large degree. Therefore, I believe iterative development where you make a plan but also review the results regularly is the most effective way.
PS: I am not a historian nor a philosopher, so please, enlighten me if I got something wrong.