The answer is much less complex. The answer is that Trump is batshit crazy and a compulsive liar.

Come on Stinky, you have run into people like this before. I know you don't want to believe it and neither do I, but facts are facts. It's called crazy for a reason, because it's beyond normal logic and reason. And it feeds on denial.

The man is crazy. Sorry. He's nuts.

*the White House* did not order any wiretapping. That is an interesting choice of words. But that is not the same as saying the executive branch did not legitimately do so. Obviously, the statement also did not confirm that any wiretapping DID take place.

He thinks if he can stay ahead of the story, he can control the story.

Not necessarily because the Trump bunch were the direct target of warrants, but because they kept having phone calls with potentially hostile foreign agents who were under surveillance.

I mean if you call a drug lord, why would you be surprised if that call is recorded?

I can not tell the difference between a Russian Oligarch and the Russian Mafia, and there may not be a difference. The US government had various sanctions against Russia last year, and with the troubles in Ukraine and the shooting down of the Passenger Airliner there, I am sure we have lots of those subjects under surveillance.

And if you keep calling a subject of interest, why would you be surprised if YOU became a subject of interest too.

...was an "unregistered" foreign agent. I hope they were recording the calls.

Flynn was in big trouble after Woolsey saw and then reported his meeting in NY with Turkish government. I suspect that Woolsey continued watching Flynn and reporting back to IC through intermediaries. Woolsey essentially became a mole in the Trump transition.