any and every institution created by humans is fatally flawed and eventually corrupted. history shows this. whether or not a society is good or bad depends on an individuals views because people get rolled over in the name of democratic progress too (usually on the outside), the only difference is how a society justifies itself to itself. and in this case there are many subjects and non subjects of Caesar that think the legion has some very good and very bad characteristics. individuals freedoms are not always at the top of a persons values.

talk to Cass or Raul about the legion and NCR (i only omit House because nobody actually knows anything about him except the courier). Cass is hilarious when she compares the NCR to L.D. Johnson and begrudgingly admits the the Legion is actually more conducive to free trade the NCR and basically that the NCR is like a dumb-ass little brother who means well but just cant get its [censored] straight. Raul states that from personal experience that the Legion territories are actually a nice place and that not everyone is a slave. where formerly they where hellish.

I can see where Caesar would think Democracy is not the answer, he educated enough to see that it didn't stop the world from burning, and maybe by attempting to unite all humanity under a single Empire will prevent the type of conflict that caused the bombs to drop. this has actually been attempted in history by many great conquerors and is actually quite effective considering our civilization is build on the ones that came before us.