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For me, this article thus far has the clearest explanation and analysis of the documents Gabbard has shared:
.....The reason [why Putin wanted Hillary to win], according to Obama’s own [initial intelligence community assessment (ICA)] intelligence, is that Moscow possessed damaging information on her and saw her as easier to manipulate.
One of the most damning findings is that the Obama-driven ICA [his rewritten one]“ignored strong indicators supporting the alternative hypothesis that, at a minimum, Putin didn’t care who won, and even had reasons to prefer a Clinton victory.”
The report goes further:
pjmedia.com
So, as in the ways of this world, leverage of compromising info about Hillary was being held onto by Putin as future blackmail currency to exert control and manipulation over her presidency...... thus showing Putin's true peference of who he wanted to win. The rest of the article lays things out with good clarity.
.....The reason [why Putin wanted Hillary to win], according to Obama’s own [initial intelligence community assessment (ICA)] intelligence, is that Moscow possessed damaging information on her and saw her as easier to manipulate.
One of the most damning findings is that the Obama-driven ICA [his rewritten one]“ignored strong indicators supporting the alternative hypothesis that, at a minimum, Putin didn’t care who won, and even had reasons to prefer a Clinton victory.”
The report goes further:
By keeping the most damaging material on Clinton in reserve, Putin was not only demonstrating a clear lack of concern for Trump's election fate, but conversely, his actions could also indicate that he preferred to see Secretary Clinton elected, knowing she would be a more vulnerable President than candidate Trump. Moscow's reserve of compromising materials would have given Putin leverage over a Clinton Administration, but not a Trump one.....

Report: Obama Knew Russia Wanted Hillary to Win—and the Reason Why Is HUGE
Putin preferred Hillary Clinton for manipulation, revealing a political narrative twist.

So, as in the ways of this world, leverage of compromising info about Hillary was being held onto by Putin as future blackmail currency to exert control and manipulation over her presidency...... thus showing Putin's true peference of who he wanted to win. The rest of the article lays things out with good clarity.