I’d say Cenk’s problem is one a lot of Democrats (and Republicans!) share: his notion that “Russia” is some sort of monolith run by Putin (see 9:28).
Tracy’s Russia spiel starting around 8:45 is right on target: Putin may exercise more control over the various power blocks that make up the Russian establishment than any US president does, but that doesn’t change the fact that there are a bunch of different people, and groups of people, with different agendas, pulling this way and that.
Putin may place limits on how far they can get from his agenda, but they’re all definitely not singing from the same hymnal.
With these ideas in hand, we can see all that Russian money going into Trump investments as efforts to get it out from under Putin’s thumb. By “oligarchs” and others whose “ties to Putin” could range anywhere from pushing their own agendas with him to him putting them in jail.
This is what makes the whole “Russia!” thing so silly.