Obama always has the goods on his rivals. It is his MO from the beginning.
It would only be surprising if he didn’t have his rivals surveilled.
So, yes, I haven’t the slightest doubt he had Trump and his inner circle surveilled, wiretapped, followed, infiltrated, both with and without warrants, both using official assets and others not even Mueller or Brennan know about. Its the way Obama (or rather, Obama’s handlers) operate.
It would go a long way toward explaining a lot of curious things about why Trump was able to pull off such a stunning upset in the 2016 election. Just to name a few:
1. Clinton sure didn't campaign like someone who thought it was remotely possible that she might lose.
2. She ignored Wisconsin and practically ignored Michigan and Pennsylvania.
3. She campaigned in places like Texas and Arizona -- which Trump won handily -- in the last days of the campaign.