Tyranny

I re-read through Cicero's Commonwealth, I think I may have missed what you are talking about. There was a ton about why one becomes a tyrant, and the mannerisms they take on, but I couldn't yet find him talking in detail about the "why" people follow tyrants. However, this is what I was able to come up with after researching about this.

"Then since the private condition is naturally exposed to fears and
alarms, the people invest him with many powers, and these are continued in his hands.
Such men, like Pisistratus of Athens, will soon find an excuse for surrounding
themselves with body guards, and they will conclude by becoming tyrants over the
very fools that raised them to dignity. If such despots perish by the vengeance of the
better citizens, as is generally the case, the constitution is re–established"

Here, he's saying that when the people realize that a tyrant is among them, that tyrant will be overthrown. So I guess when thinking about the picture, the people won't over throw their dictator unless 1. The majority actually want's the ruler gone. 2. They have the man power to do it. 3, They know what kind of government they want after that.
What I've gathered from what Cicero said is that people will put someone into power, someone in whom the people put their trust to rule over them. If said person were to rule wisely, then the people will keep them. However, if this person were to abuse the power given to them, then the people will accordingly dispose of them.
He saying that people won't find a tyrant to put in power, it's if the person becomes a tyrant, and they will only get rid of the corrupted person if the majority thinks that what the tyrant is doing is wrong.

After doing more research,(outside of Cicero) it was interesting to realize that freedom has a big part to do with this. For the most part, people want to be led, and choices need to be made. Since we come from a fallen nature, it's easy for us to teeter to a tyrannical basis. Repeating what all of the philosophers we've been studding said, without the proper morals, we will always tend towards chaos.