In all honesty, I don't feel bad for Rondo.
For one, as a result of the Big Three, he'll never have to face that list with John Stockton (and soon, Steve Nash), the greatest pass-first point guard who didn't win a ring.
But yet, w/o being on that list, he didn't develop a reliable mid-range jumper like the prior prodigy passer, Jason Kidd. And Kidd's ring was the luck of being at the Ray Bourque moment, at the right time, in Dallas towards the end of his career.
So yes, Rondo's got his moments in the sun but at the same time, let's face it, during the playoffs, opponents know how to defend against a Rondo-led squad.