see linked article below.
personally i see him as a strategist but too stubborn to adapt to circumstances. it was clear he was trying to control russia's near abroad and western europe via the supply of gas, the expansion of russia's military and the corruption of neighbouring politicians. much of this strategy doesn't work where shale is a plentiful resource and popular will is able to express itself and throw out his puppets. so he resorts to the military. we see this in places like georgia and ukraine and in the implied threats to the baltic countries and scandinavia.
it's very clear how critical it was to his strategy to control ukraine. but in employing military means he damages russia itself. he probably thought russia's oil made it economically immune. so much for that idea.
instead of looking to build a larger geography, russia needs a less monolithic economy of its own. economic integration will reduce russia's freedom of action but ought to increase its wealth. that ought to satisfy a peaceful leader. but not a megalomaniac.
http://www.forbes.com/sites/gregsatell/2014/12/21/what-will-putin-do-now/
"While many in the west think that Putin is a master strategist, most people with inside knowledge of the Kremlin believe otherwise. At best, he appears to be a talented tactician, seizing opportunities where he finds them, but operating without a concrete long term plan.
Evidence would seem to bear this out. Like a drunk poker player, at each stage Putin has consistently doubled down on his bets while facing a decreasing expected return. When the crisis began, his aim was to create a Eurasian Economic Union to rival the EU. Today, he’ll be lucky to avoid a complete collapse of the Russian economy, if not his own government as well.
So Putin’s options now are very limited, but they will likely get better in time. No one knows what will happen in six or twelve months. It is quite possible, even likely, that an opportunity will present itself and Putin is looking to pounce.
He will also, if history is any guide, overreach once again and the story will go on."