I still have yet to see how Trump has been 'kissing Putins Ass'. We still have sanctions in place in Russia to include individuals and corporations, Trump has made no qualms about the fact that nothing could come from this meeting, or something, we'll have to wait and see.
Moreover, I haven't heard Trump say more than that about Putin. Everyone claims Putin has something over Trump, but that would imply total control. If that were true, why would Putin allow Trump to do things like encourage the capability of bilateral trade agreements with the US instead of a globalised treatise which would empower Russia as a member of the global community? Or allow Trump to persuade the Europeans' most powerful country--Germany--to disallow more Russian oil into the country? Oil is Russias lifeblood, thats why they hold the Caucasus and the Ukraine, Oil and access to western ports.
Putin, if he was in control, would never allow these actions, nor would he allow for the blatant hegemonic shift thats occurring between the United States and China.
Consider these things before wondering what questions Trump might pose the Russian. Putin is not the most powerful man in the world, Trump is, because his power is vested in and by us. Putin has an 85% approval rating, thats according to American polls, but the problem is that its simply a cult of personality under the authoritarian nationalism of Putin's Russia.
Trump, on the other hand, comes from a position of strength because Russia has nowhere NEAR the influence on the global community that we do. This is true because it was America's globalist tendencies early in the 20th century which led to the creation of global hegemony controlled by the United States. The Soviet Union fell, leaving America the SOLE SUPERPOWER of the 21st century, our military is 20 years and 2 generations more advanced than Russias, our economy is hundreds of times larger, and weve proven that capitalism works far better than communism. Trump embodies all of those things, so its hard to argue that Trump wont stick it to Putin, at the least, honestly. Trump is not afraid, that much is clear. In contrast with the politics of Obama, Trump is not timid, and theres a chance Putin and he may even get along! So the questions over which you speculate are not knowable yet, and shouldn't even be asked because its irrelevant what we think he might do. In an event like this one, where we have no say, no public voice, what becomes important is what he, our representative, actually does. Until then, speculation and imagination create strife because they create an expectation and when people dont get what they expect, they get upset...
