Unfortunately, Pollyanna has received a bad rap as a sort of brainless hyper-optimist, even though the actual book makes it clear that she was merely seeking the good in even the worst situation—and according to Torah, it is correct to do so.
However, many people misunderstand the obligation to give the benefit of the doubt, causing harm to themselves and others, and transgressing other serious prohibitions.
At one point, I caught myself doing it and noticed many others doing it, so I looked to our Sages for advice.
Doing so clarified what really needed to be done and enabled me to live a more honest, more balanced, and overall better life.
However, many people misunderstand the obligation to give the benefit of the doubt, causing harm to themselves and others, and transgressing other serious prohibitions.
At one point, I caught myself doing it and noticed many others doing it, so I looked to our Sages for advice.
Doing so clarified what really needed to be done and enabled me to live a more honest, more balanced, and overall better life.
Rebbi Levi & the Kli Yakar vs. Malignant Optimists & Flying Monkeys
Torah lectures and literature contain countless admonitions and stories illustrating how vitally important—and correct—it is to give the benefit of the doubt.
Unfortunately, doing so in the wrong way leads to a severe transgression of the Torah prohibition of chanifah (among other severe transgressions, such as "standing in the blood of your neighbor" and believing lashon hara and placing "a stumbling block before the blind," and more).
But let's focus on chanifah.
Commonly translated as "flattery," our Sages define chanifah as a form of falsehood. Orchot HaTzaddikim (Ways of the Righteous) and Shaarei Teshuvah (Gates of Repentance) both elaborate on what constitutes chanifah.
Essentially, chanifah is:
In the field of Narcissism, some forms of chanifah are known as "malignant optimism" and "flying monkeys."
Flying monkeys and malignant optimists are the "nice," well-meaning people who enable the worst atrocities in history as exemplified by the everyday Communists, civilian Nazis, Left-Wing citizens in Western countries and Israel today, and more.
I guess we've all seen very nice and well-intentioned people stubbornly defend and rationalize the actions and intentions of very harmful people—and they tend to pressure others to do the same.
The rationalizations are always given under the misguided notion that it's obligated by the Torah as the mitzvah of giving the benefit of the doubt and seeing others in a positive light (AKA, an ayin tovah).
Unfortunately, doing so in the wrong way leads to a severe transgression of the Torah prohibition of chanifah (among other severe transgressions, such as "standing in the blood of your neighbor" and believing lashon hara and placing "a stumbling block before the blind," and more).
But let's focus on chanifah.
Commonly translated as "flattery," our Sages define chanifah as a form of falsehood. Orchot HaTzaddikim (Ways of the Righteous) and Shaarei Teshuvah (Gates of Repentance) both elaborate on what constitutes chanifah.
Essentially, chanifah is:
- any behavior or speech that implies a forbidden behavior is permitted, or even praiseworthy
- behaving or speaking in a way which implies that an evil or sinning person is perfectly okay, or even righteous, whether only to others or to the sinning person directly
In the field of Narcissism, some forms of chanifah are known as "malignant optimism" and "flying monkeys."
- The Malignant Optimist: This is the ever hopeful victim who always sees the innocent intentions and the good potential in their abuser.
- Flying Monkeys: Named after the winged primates who enthusiastically did the bidding of the Wicked Witch of the West in The Wizard of Oz, "flying monkeys" follow the abuser's bidding, which the abuser uses to increase the torment of his or her targeted victim. "Flying monkeys" may act out of loyalty or misguided "good" intentions or out of fear, not realizing that the abuser will scapegoat them whenever necessary without a second thought or any remorse.
Flying monkeys and malignant optimists are the "nice," well-meaning people who enable the worst atrocities in history as exemplified by the everyday Communists, civilian Nazis, Left-Wing citizens in Western countries and Israel today, and more.
I guess we've all seen very nice and well-intentioned people stubbornly defend and rationalize the actions and intentions of very harmful people—and they tend to pressure others to do the same.
The rationalizations are always given under the misguided notion that it's obligated by the Torah as the mitzvah of giving the benefit of the doubt and seeing others in a positive light (AKA, an ayin tovah).
 Flying Monkeys |  Malignant Optimist |
For many decent people, it is hard to accept that some people they know and even like do consistently hurt others and actually mean to.
Such people may even enjoy it.
These types consistently behave badly with bad intentions (even as they often feel totally justified and will indeed offer convincing rationalizations for their harmful behavior. Again. And again. And again.)
Even their good deeds are usually done for negative reasons.
It is not giving the benefit of the doubt to encourage oneself or others to assume ignorance or lack of intention when there is a pattern of awareness and bad intention.
Such people may even enjoy it.
These types consistently behave badly with bad intentions (even as they often feel totally justified and will indeed offer convincing rationalizations for their harmful behavior. Again. And again. And again.)
Even their good deeds are usually done for negative reasons.
It is not giving the benefit of the doubt to encourage oneself or others to assume ignorance or lack of intention when there is a pattern of awareness and bad intention.
(Just to be clear: When this topic refers to bad or abusive people, it does not mean basically decent people who are going through a temporarily hard time (exhausted, stressed, or sick) or who make mistakes or who possess one or two traits that regularly mess them up in certain areas. Bad or abusive people consistently behave harmfully over the long term and even their good behavior tends to be motivated by negative intentions.)
So how can we focus on the good in others and give the benefit of the doubt without becoming malignant optimists or flying monkeys?
To start with, we have the timeless example of Rebbi Levi of Berditchev (1740-1809).
Rebbi Levi‘s Do’s and Don’ts
Many of us know the story of how Rebbi Levi approached a Jew who was smoking on Shabbat. Rebbi Levi first inquired as to whether the Jew knew it was Shabbat. Perhaps the Jew didn’t realize that smoking was forbidden on Shabbat? Perhaps the Jew had some legitimate reason for smoking on Shabbat?
When the Jew’s answers showed that he certainly knew exactly what he was doing, Rebbi Levi then proclaimed: "Lord of the Universe, see the holiness of your people! They’d rather declare themselves sinners than utter a lie!"
Note what Rebbi Levi did not do:
Instead, Rebbi Levi completely sidelined the Jew’s Shabbat behavior and detoured around to another quality within that same Jew: honesty.
And Rebbi Levi also paused from interacting directly with the willfully sinning Jew and instead turned to address Hashem.
(Meaning, Rebbi Levi didn’t tell that Jew nor did he say to others, "Well, violating Shabbat isn’t so great, but at least he’s honest about it.")
It is true that the Jew was intentionally violating Shabbat.
It is also true that the Jew refused to lie about it.
There is no, "Yes, but...."
Rebbi Levi did not in any way justify this very public and willful transgression. Instead, he found something else positive to say about his fellow Jew and then re-routed it to Hashem.
He also prayed for people--even the most horrible people.
Of course, this example doesn't totally address the issue of dealing with a very harmful person. Someone can violate Shabbat, yet behave well in other areas.
And the opposite is also true.
To start with, we have the timeless example of Rebbi Levi of Berditchev (1740-1809).
Rebbi Levi‘s Do’s and Don’ts
Many of us know the story of how Rebbi Levi approached a Jew who was smoking on Shabbat. Rebbi Levi first inquired as to whether the Jew knew it was Shabbat. Perhaps the Jew didn’t realize that smoking was forbidden on Shabbat? Perhaps the Jew had some legitimate reason for smoking on Shabbat?
When the Jew’s answers showed that he certainly knew exactly what he was doing, Rebbi Levi then proclaimed: "Lord of the Universe, see the holiness of your people! They’d rather declare themselves sinners than utter a lie!"
Note what Rebbi Levi did not do:
- He did not express any opinion indicating that it was okay, understandable, funny, or "cute" to be smoking on Shabbat.
- He didn’t insist that the Jew was violating Shabbat by accident after the Jew clearly showed that he was violating Shabbat with full knowledge and intent.
- He didn’t rationalize that the smoking Jew's possibly "difficult childhood" or "having a bad day" as a justification of the Shabbat violation. (Meaning, Rebbi Levi did not say it's okay or permissible to violate Shabbat because of a mood or certain feelings.)
Instead, Rebbi Levi completely sidelined the Jew’s Shabbat behavior and detoured around to another quality within that same Jew: honesty.
And Rebbi Levi also paused from interacting directly with the willfully sinning Jew and instead turned to address Hashem.
(Meaning, Rebbi Levi didn’t tell that Jew nor did he say to others, "Well, violating Shabbat isn’t so great, but at least he’s honest about it.")
It is true that the Jew was intentionally violating Shabbat.
It is also true that the Jew refused to lie about it.
There is no, "Yes, but...."
Rebbi Levi did not in any way justify this very public and willful transgression. Instead, he found something else positive to say about his fellow Jew and then re-routed it to Hashem.
He also prayed for people--even the most horrible people.
Of course, this example doesn't totally address the issue of dealing with a very harmful person. Someone can violate Shabbat, yet behave well in other areas.
And the opposite is also true.
So this brings us to the Kli Yakar’s discussion of King Achashverosh (a truly bad person) in Parshat Titzaveh 28:39 (which in non-leap years, comes out right before Purim, so the Kli Yakar found the Torah portion's connection to the Purim story).
Azamra! Finding the Diamond Chip Floating around in the Mountain of Sludge
Mountain of Sludge
The Kli Yakar describes Achashverosh as karov l’shogeg—"close to being an unintentional sinner."
This is a radical statement considering how many Sages consider Achashverosh to have been even more evil and more of a Jew-hater than Haman.
Likewise, the Kli Yakar also calls Achashverosh "that rasha"—a wicked person who sins intentionally against both people and God. The Kli Yakar also quotes Megillah 12, in which the angels themselves refer to Achashverosh as "the rasha."
(Just so there's no room for doubt.)
Furthermore, the Kli Yakar explains that Achashverosh even consulted with the Jewish Sages of his time as to the holy symbolism of the Priestly Garments and holy vessels.
And those Sages, in addition to explaining the symbolism, also clearly told him that wearing these garments was absolutely forbidden for anyone other than the Kohen Gadol—the High Priest.
Nahafochu—Twist!
Yet the Kli Yakar also explains that the appallingly blasphemous things done by Achashverosh—like wearing the Priestly Garments, holding a feast using the holy vessels from the Beit Hamikdash, and even symbolically acting out parts of the Priestly Service with his servants—were meant by Achashverosh as an atonement for himself!
(See the Kli Yakar on Parshat Titzaveh for the exact atonements rendered by the different garments.)
As the Kli Yakar explains,
This is a radical statement considering how many Sages consider Achashverosh to have been even more evil and more of a Jew-hater than Haman.
Likewise, the Kli Yakar also calls Achashverosh "that rasha"—a wicked person who sins intentionally against both people and God. The Kli Yakar also quotes Megillah 12, in which the angels themselves refer to Achashverosh as "the rasha."
(Just so there's no room for doubt.)
Furthermore, the Kli Yakar explains that Achashverosh even consulted with the Jewish Sages of his time as to the holy symbolism of the Priestly Garments and holy vessels.
And those Sages, in addition to explaining the symbolism, also clearly told him that wearing these garments was absolutely forbidden for anyone other than the Kohen Gadol—the High Priest.
Nahafochu—Twist!
Yet the Kli Yakar also explains that the appallingly blasphemous things done by Achashverosh—like wearing the Priestly Garments, holding a feast using the holy vessels from the Beit Hamikdash, and even symbolically acting out parts of the Priestly Service with his servants—were meant by Achashverosh as an atonement for himself!
(See the Kli Yakar on Parshat Titzaveh for the exact atonements rendered by the different garments.)
As the Kli Yakar explains,
His main intention was to wear the Priestly Garments to be an atonement for him….he thought that all this would ascend as [God’s] Will, as if everything was performed on the actual Altar….he said:
"I will use these vessels in their prescribed manner, with the eating exceeding the drinking. Then I will not desecrate their holiness."
Achashverosh also wanted to avoid the punishment meted out to Belshatzar, who also abused the sanctity of the holy items.
And this explanation demonstrates one of the spectacular things about Judaism and the secret to greatness: the ability to embrace paradox.
Finding a Couple of Diamond Chips Does Not Mean the Mountain of Sludge is a Hidden Diamond Mine
Achashverosh had a couple of good intentions—after all, if he craved atonement (no matter how superficial), he must have had some awareness that he was doing the wrong thing and that there is Din (judgment) and that there is a Dayan (a Judge), whom he wanted to appease.
And so the Kli Yakar, in the same passage where he twice refers to Achashverosh as a rasha, also deems him as "karov l’shogeg—close to being an unintentional sinner"—close, but not quite.
And this explanation demonstrates one of the spectacular things about Judaism and the secret to greatness: the ability to embrace paradox.
Finding a Couple of Diamond Chips Does Not Mean the Mountain of Sludge is a Hidden Diamond Mine
Achashverosh had a couple of good intentions—after all, if he craved atonement (no matter how superficial), he must have had some awareness that he was doing the wrong thing and that there is Din (judgment) and that there is a Dayan (a Judge), whom he wanted to appease.
And so the Kli Yakar, in the same passage where he twice refers to Achashverosh as a rasha, also deems him as "karov l’shogeg—close to being an unintentional sinner"—close, but not quite.
And he thought he would be exempt [from sin]....[But] all this was just a fantasy and there was no actual avodah….for there was nothing in all his deeds except fantasy alone.
At the end of the day, Achashverosh was still a hopeless rasha.
Even Mordechai HaYehudi, the spiritual giant of that generation who saved Achashverosh’s life, didn’t try to change him.
Furthermore, being married to Queen Esther, a paragon of emuna and everything good, had no effect on the degenerate king.
And yes, Achashverosh also did some other really nice and merciful things, like glorifying Mordechai for saving his life, and not killing Queen Esther for going against serious protocol, and also by sending out an edict that encouraged the Jews to defend themselves against his previous edict, thereby discouraging the Jew-haters from killing Jews.
(Although this wasn't him so much as Hashem orchestrating angels and events behind the scenes.)
Despite these good deeds and despite his desire to preserve the sanctity of the Temple vessels and despite his admittedly superficial desire for personal atonement...
...Achashverosh was still NOT "basically good underneath it all."
Some people aren’t. Really.
But they still have their random good points.
No justifications, no excuses, no rationalizations, no validations, and no white-washing.
Just a couple of good points.
And that’s all we need to acknowledge in such people.
Even Mordechai HaYehudi, the spiritual giant of that generation who saved Achashverosh’s life, didn’t try to change him.
Furthermore, being married to Queen Esther, a paragon of emuna and everything good, had no effect on the degenerate king.
And yes, Achashverosh also did some other really nice and merciful things, like glorifying Mordechai for saving his life, and not killing Queen Esther for going against serious protocol, and also by sending out an edict that encouraged the Jews to defend themselves against his previous edict, thereby discouraging the Jew-haters from killing Jews.
(Although this wasn't him so much as Hashem orchestrating angels and events behind the scenes.)
Despite these good deeds and despite his desire to preserve the sanctity of the Temple vessels and despite his admittedly superficial desire for personal atonement...
...Achashverosh was still NOT "basically good underneath it all."
Some people aren’t. Really.
But they still have their random good points.
No justifications, no excuses, no rationalizations, no validations, and no white-washing.
Just a couple of good points.
And that’s all we need to acknowledge in such people.
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