If Obama and Hillary were sure she had enough legal and illegal votes to win all the swing states, why did Obama wire tap Trump’s computer at Trump Tower? Did they intend to blackmail him with bogus Russia information after the election? Inquiring minds want to know what their motivation was.
There must be a significant unknown component missing in all this. It seems everyone was pretty sure Clinton was going to win, so why the tap, a losing Trump would have been insignificant. Unless, they were interested in finding out what Trump knew about their newly elected Hillary.
I think the mistake you are making is in using the term "Obama and Hillary."
Ten bucks says Obama's team also had Hillary Clinton under surveillance as well. Since she was running as a war-mongering globalist who would basically mirror about 95% of what we saw with the George W. Bush administration, I'm sure they didn't trust her any more than they trusted Trump.
If anything, they'd be more likely to use the Clinton surveillance for real blackmail if she had won -- since they already had a treasure-trove of information about her links to Russia from her days as Secretary of State.
Same thing for Nixon's cronies. He was going to kick McGovern's ass, but Nixon's peeps still did the bugging.