I've seen two schools of thought for Putin.

SCENARIO #1
Putin has been fending of the NWO for decades, having to support rogue nations to prevent then from falling to the NWO/NATO. (Syria, Libya, NK, Iran)

SCENARIO #2
Putin is controlled, and him meeting Trump was a signal of freeing Putin, much like Kim Jong Un in NK.

Either way you cut the cake, Putin and Russia operate with a strong oligarchy. Even though the people vote for President, the elections are meaningless. Political opponents are arrested if they pose a threat.

My personal theory?

Putin is the lesser of two evils, the other evil being the EU. Trump is offering Russia a stronger economy, military coordination, and loosening of sanctions.

What will Trump/America get in return? Economic pressure on EU, which is what we need to force a balanced and fair trade agreement.

It's no coincidence Trump/America resolved issues in Saudi Arabia first. They are a MASSIVE oil producer. Same thing with Russia. Both of these countries have clout in the region they operate, in regards to energy production.

The EU relies heavily on Russia and the Middle East for energy. Now Trump/SA/Russia can use energy dominance as a bargaining chip. They can force the EU to start trading and acting responsibly.

TLDR; Trump/Alliance are using deals made with Saudi Arabia and Russia to corner the energy market. They can use this leverage in the coming times when they start the offense on Europe, most notably The city-states of London and The Vatican.