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andyp
When I watched the Alexei Navalny documentary about Putins' massive villa I kept on having somewhat similar thoughts - he's so loaded already, has way more than he can spend on anything, pretty much even toilet brushes are made of gold in that villa - why can't he just keep status quo and enjoy it?
These wars are to boost his ratings, I get it, but it doesn't feel like he's losing grip on power anytime soon. All the oligarchs would probably be interested in keeping the status quo.
As of dictators retiring - not sure but it struck me a little bit that Gorbachev and Yeltsin who were prominent figures of the Soviet Union were (edit - sorry, Yeltsin is no longer alive) still alive and just casually chill somewhere in Russia. They probably were not as evil as their predecessors but they were still strongly involved with the whole evil empire.
Yeltsin practically handed power to Putin and everyone supported him back then because they thought it's finally a leader that will lead them to bright future.
P.S. this is the documentary by Alexei Navalny about Putins' villa for the ones who haven't seen it and got time. English subtitles and dubbed versions are also available https://youtu.be/ipAnwilMncI