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Alaska: An American Colony, Stephen Haycox, 2002.

page 85:

"In 1796, Catherine II died at age sixty-seven. She had stamped her character and her name on Russia during the generation of her reign. During the brief ascendancy of her son, Emperor Paul (Paul I), Rezanov rose still higher in the court, becoming secretary of the senate in 1797."
page 88:

"Catherine the Great never intended that her son Paul—weak, mentally unbalanced, and ineffectual—should succeed her. Instead, she favored her grandchildren, particularly Alexander, who was both bright and competent and shared her understanding of and commitment to rational government. In March 1801, Alexander authorized a palace coup in which he replaced the tsar, who was murdered a short time later. The charge in government had no effect on the organization of the new Russian American Company (RAC). Alexander I approved establishing the RAC headquarters in St. Petersburg, which kept it completely under Nikolai Rezanov's protection and direction. Among other things, Rezanov urged members of the court and the aristocracy in St. Petersburg to invest in the new entity, which they did readily, including the tsar."

https://books.google.com/books?id=natRq6WCu4oC&pg=PA88&dq=%22Catherine+the+Great+never+intended+that+her+son+Paul%22&hl=en&sa=X&ei=cVoHVaOnAarIsASZ1ICYCQ&ved=0CB4Q6AEwAA#v=onepage&q=%22Catherine%20the%20Great%20never%20intended%20that%20her%20son%20Paul%22&f=false
This is the stuff of Greek tragedy. I mean, Holy Shit. Alexander I set in motion the course of events which led to the murder of either his father or uncle, or maybe he intended it all along.

Just maybe Catherine could have anticipated some of this and/or she either lives longer or gets started earlier.

Now, it is rare to have a monarch who moves toward democracy, but it has occasionally happened in human history, right? Maybe she could have encouraged her son Paul to take up new business ventures or something else which tends to reward risk and different ways of doing things.
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