Pirke Avot 1:6, 7- When Should We Give People the Benefit of a Doubt?

In Christian Scriptures, Matthew (7:1) says "Judge not that ye not be judged."  To put it in more secular parlance, "Who are you to judge?  You've made mistakes in the past.  Back off!"  Although the reasoning for the sentiment is different, I would contend that the verse from Matthew has influenced the American concepts of tolerance and understanding to the point where we think we have no place to judge others. 

We find ourselves in yet another situation in which Judaism is counter-cultural.  In Jewish thought, it is not so much if we can judge others, but how we should go about judging others.  Although we don't realize it, many still subconsciously make judgments about others.  And since it plays such a key role in our interactions with other people, it should occur and matter.  This brings me to the most well-known verse in Judaism that tells us how to go about judging others:

והוי דן את כל האדם לכף זכות.

"Judge the whole of a man to the side of merit." -Pirke Avot 1:6

 
Are we to give every man the benefit of a doubt?  Rashi's commentary on the verse would suggest so when he said that you should "give everyone the benefit of the doubt, and assume that a person's actions are meritorious.  For doing so, you will be judged favorably."  I am going to take a few issues with this commentary.  One, I am more prone to think that Rashi was reading this third portion of the mishnah within in the context of the two first thirds (i.e., it applies solely to one's רב and חבר).  Second, זכות is a tricky word to translate, since it can mean "merit, favor, acquittal, credit."  Context better helps with what זכות means.  Since the direct object is "the whole of a man (כל האדם)," as opposed to "humankind" (המין האנ), I am linguistically much more inclined to believe that the verse is telling us to judge based on the entirety of a human being and his merits.  Fourth, and what I find to be most important, is what Rabbi Nitai, has to say in the next verse:
 

"Keep far from an evil neighbor, do not associate with a wicked man, and do not abandon the belief in retribution." -Pirke Avot 1:7              

 
If Rabbi Nitai really was trying to teach us that we should give everybody the benefit of a doubt, he wouldn't tell us in the next verse to keep away from evil people with a ten-foot pole!  We have established that we should not associate with evil people in any way, shape, or form, and that we should not give everyone the benefit of a doubt. 
 
What about righteous people?  What do we think when they ostensibly have done something wrong?  Maimonides says that if there is the slightest bit of doubt, you doubt him favorably.  As long as that reasonable doubt exists, you are not permitted to judge him unfavorably.  As the Talmud (Shabbat 97a) says, "He who suspects the upright should be whipped." 
 
A majority of individuals are neither overtly pious nor overtly evil like the tzaddik or the rasha.  What do we do about the person who would really be considered neither?  As R. David Rosenfeld points out from Maimonides' commentaries, "If an act leaves little room for doubt -- and the person is not exactly known for his saintliness -- one need not find some favorable interpretation to his act," which is another way of saying "don't pull of acrobatics of implausibility to justify his actions."  I have found that in life, clear-cut scenarios are not as voluminous as one would like to think.  Many situations have multiple reasonable doubts.  How do we perceive such an individual at that point?
 
To briefly re-cap, we are now dealing with a majority of individuals in a majority of situations.  The individual is neither defined as particularly righteous nor particularly wicked.  The situation is really ambiguous and unclear.  In dealing with this scenario, we should give the individual the benefit of a doubt.  Although it's a more theocentric message, I like how R. Rosenfeld shows why this is important:
 

When we view others in such a manner, it sends a different message to G-d. I know Your creations are good human beings. They stumble and fall at times, but I have not lost faith in them as a result. They mean well, and I'm sure they'll pick themselves up again and try harder. And this is the attitude we should only wish G-d would have towards us. He (more than anyone else in creation) knows that human beings are basically good creatures. We have good souls and active, restless consciences. If we recognize the innate goodness in others, chances are we will see it in ourselves equally well.

 
The Jewish view on judgmentalism and giving people the benefit of a doubt is neither credulous nor overtly criticizing.  We judge blatant evil by distancing ourselves from it, whereas we give a near absolute benefit of a doubt to the righteous person, unless the evidence convicting him is so damning that cognitive dissonance is blinding you from making an objective judgment.  As for the gray area that we are most likely to encounter with people in the middle ground, when you find reasonable doubt, err on the side of goodness.  Rather than cultivating paranoia, cynicism, and animosity by focusing on shortcomings, we can focus on mercy, loving-kindness, and optimism.  When making judgments, give the benefit of a doubt as often as you can.  As the Talmud teaches, "Anyone who judges others favorably will be judged favorably in Heaven (Shabbos 127b)."  It's good for society and good for the soul.