Are Plato's "Philosopher Kings" truly free?

I have been reading Plato since I was a college freshman, and each time I come away a little more enlightened.  His writings and his ideas are deep and hard to comprehend, but once I do understand them, I get the ever-satisfying "light-bulb-effect".  Pow!  Oh, so THAT'S what he meant! 

The first time I experienced this "light-bulb-effect" was in sophomore Philosophy.  We were talking about Plato's allegory of the cave.  Granted, I had read about it the night before, but it hadn't made much sense to me.  When Dr. Stone began to lecture on it, though, I began to comprehend.  When I went back to read the text that night, everything I finally got the big picture. 

Instead of reiterating Plato's allegory, I have included a brief video that illustrates his points:

 

I want to focus on the escaped prisoner, the one who was actually able to experience life.  This is what has always fascinated me about Plato's allegory - that there are a select people who are able to free themselves from the mundane and who are able to understand the world.  In World Lit I, the term "philosopher king" was used to described these escaped prisoners.  We learned that the philosopher kings had a responsibility: it was their job to enlighten the prisoners who were still bound.  

So, I wonder if it really was a blessing or a curse to be set free?  If we are freed from the world as we know it and are able to become enlightened, what use would it be if it becomes our duty to enlighten the others, who are still trapped.  To me, this is like trying to describe a sunset to a person who was born blind.  Wouldn't the philosopher king, then, be trapped again?  He would not be bound to a cave wall, but to those who remain imprisoned.  He could not enjoy life - not fully, at any rate - while trying to enlighten others.  So, are the philosopher kings truly better off?  Is it better to become enlightened only to be bound to those who remain ignorant or to never have been freed at all? What do you think?