According to Charles Krauthammer, President Putin of Russia sees himself in very historic and transformational terms :

"He can already see the history textbooks: Catherine the Great took Crimea, Vlad (the Great?) won it back. Not bad for a 19th-century man."

I don't know if he is "Vlad the Great" but President Putin is like the offensive coordinator who keeps throwing the long pass and scoring.  He's concluded that the other side does not have much of a pass defense.  He keeps throwing and scoring.

There is one more piece to putting the empire together.  It is Cuba, the island 90 miles away from the US and a very nice warm spot for the Russian Navy to go around the world.

How does he get Cuba back?  The answer is money and Putting has plenty of that these days.  . 

First, he goes to Raul Castro and offers a lifeline. Cuba needs credit and would literally love "a sugar daddy" again.

Second, another round of Russian aid would keep the Castro brothers in power even longer.   It could replace the subsidized oil that they've been getting from Venezuela.  It would also draw the US's attention or give the Castro brothers the kind of relevance that they crave.

Third, they won't have to pay back all of those loans to Western countries.  Russia would take care of that, as it did between the Missile Crisis and the collapse of the USSR.   It's "Happy Days are here again" for the Castro dictatorship.

Again, Putin wants to put the empire back together and Castro needs a lifesaver.  It is the exactly the perfect storm that could put these two nations back together.

Yes, it is a long shot.  However, stranger things have happened.   After all, didn't Russia sign a memorandum in 1994 respecting Ukraine's borders?  Didn't we "reset" relations with Russia in 2009?

Yes, there is a "Twilight Zone" element to my post but stranger things have happened. 

P. S. You can hear CANTO TALK here & follow me on Twitter @ scantojr