I don’t know who was already working with Trump at the end of 2015, but he was politically active at the time, and certainly had begun assembling an advisory group. It may very well turn out that some of those people were trying to financially capitalize on Russians trying to cozy up to a potential presidential candidate. (the most obvious possible criminal activity).
That said, I think it’s highly probable that Obama’s very insular team suffered a degree of group think hysteria, and were absolutely convinced that Trump intended to create a strong man government.
I believe those convictions drove them to skirt or violate several intelligence rules in order to deliberately interfere with Trump’s ability to govern. To me, their willingness to violate laws in order to limit the effectiveness of a freely elected president is far more serious, and a far greater danger to democratic governance than any “deals Trump could possibly have tried to cut with some Russian oligarch.
The combination of Rice collecting reams of “incidental” intelligence reports of Trump staff. her unmasking requests to the NSA for several Trump staffers, the inclusion of Ms Farkas (outside the government) in determining a strategy to deal with Trump, Obama’s executive order directing the NSA to share raw intelligence data, and the almost immediate leakage of that intelligence to the NY Times, adds up to a criminal conspiracy to undermine a freely elected president. It borders on treason.
Take a look at just how much of a train wreck it already is;