Can a lifetime of goodwork exempt one from an error of judgement made in a moment of weakness?

This sure is going to be a controversial post.

A New York court sentenced Mr. Rajat Gupta, former director of Goldman Sachs Group Inc., to two years in prison for leaking corporate secrets to Wall Street. The sentence comes months after Mr. Gupta was found guilty of passing confidential information about the bank to the hedge fund of Raj Rajaratnam, a friend and business associate.

Two disclaimers before I come to heart of the issue.

a. No denying the fact that Mr. RG's achievements were indeed one of the finest
b. This post is with all due respects to RG and his admirers. I don't intend hurting anyone's sentiments.

This post is however trying to address a larger issue. Can a lifetime of good work exempt one from an error of judgement made in a moment of weakness? I would put forth the five questions which are bothering me..

1. In someways and form isn't every crime an error of judgement made in a moment of weakness?

2. Aren't people who have done a lifetime of good work supposed to be more evolved and mature? In which case won't their level of judgement be naturally more evolved and well placed?

3. Speaking of "Moment of weakness", aren't these evolved folks prone to less "Moments of weakness" than an ordinary Joe on the street for whom a "moment of weakness" may mean choosing between life and death.

4. Next, assuming that it was indeed an "error of judgement" in a "moment of weakness", Shouldn't one come clean at least when one was caught? However, Mr. RG's reaction was "I am stunned and shocked by the proposed action.  Let me assure you, I have done nothing wrong.  The SEC's allegations are totally baseless" (based on a communication dated March 2011)

5. Summarizing my case, being less prone to "moments of weakness", being better placed in one's  "judgement" and having denied the whole issue as baseless, does one indeed deserve leniency?

Views, answers, comments and criticisms are welcome. However be considerate that you are dealing with an individual (yours humbly) whose view of the world in issues like these is largely binary.