Trump, for 45 years, was just some rich guy in NYC. The USSR, for much of the early / mid Trump period, had significant money issues, and the Russian Federation, under Yeltsin, was flat broke. To my knowledge, Trump made zero effort to extoll the virtues of communism or to denigrate the United States in any sort of public manner, which would be the only use for a semi-famous rich real estate dude in NYC. Much the opposite, he embraced capitalism.
The extent of my knowledge of Trump, before he ran for President, was that he had some casino's and hotels. Mike Tyson liked him, and he was on that stupid show, The Apprentice, which I never, ever watched. The most significant things of note he did was get in a public fight with the mayor of NYC over zoning, and his involvement with the Central Park Five case.
Then all of a sudden, in his early 70's, he decides to run for President. The initial days of his campaign were funny. He was a train wreck and America could not look away.
To this day I believe Russia never expected Trump to win and was intending to damage the future Clinton Presidency by hacking her email and dripping it out. I suspect they had much, much more information, which they would have released periodically throughout her tenure. We only ever saw one person's emails from Guccifer 2.0, and that email server had a lot of other shit on it. Every press conference Hillary or her Press Secretary had would have been about some new revelation about Clinton.