The 49*49 Principle: Embracing Complexity over Simplicty
A discussion on seeing all sides of an argument.
Case Study

Every year, the local Federation board chooses an outstanding leader to honor at the annual gala. The goal is not only to help encourage increased giving from the honoree but also to showcase the values and character of the leader in order to model the kind of positive leadership that the Federation values and wants to encourage others in the community to follow in their footsteps. You are the chair of the Federation's board and there is great pressure on you to appoint the proper honoree. The leading candidate not only fits this description as an outstanding leader but has already agreed to a sizable six figure gift and is excited to help engage some of his other high capacity friends who are not current Federation donors.

There is also a hotly contested election in your community. You learn that your honoree has aligned themselves closely with one of the candidates, including giving significant donations and hosting events for the candidate. You know this candidate is a contentious figure loved by some, hated by others. This election is beginning to gain national attention and it is likely that the candidate and your honoree will be in the national press related to this issue.

While the honoree's political activism is not yet public, you know that it will come out eventually and that his partisan views have the potential to set off an explosive fight in the community. While there are certainly community members that agree with the views of the honoree, you also know that there is a large segment of the Jewish community who would consider his views as reason to prevent him from being honored.
What is your first instinct on how to handle this as the chair of the committee?

(ג) . א"ר ינאי לא ניתנו דברי תורה חתוכין אלא כל דבר ודבר שהיה הקב"ה אומר למשה היה אומר מ"ט פנים טהור ומ"ט פנים טמא. אמר לפניו רבונו של עולם עד מתי נעמוד על בירורה של הלכה. אמר לו (שמות כג ב) אחרי רבים להטות. רבו המטמאין טמא רבו המטהרין טהור.

Rabbi Yanai said: The Torah was not given in a clear-cut manner, rather on every statement that G-d said to Moses, He would say forty-nine reasons (panim, lit. faces) the matter could be pure, and forty-nine reasons why the matter could be impure. He (Moses) said to Him, ‘Master of the Universe, when will we know the truth (or clarification) of the matter?’ He said to him (Moses): ‘Go according to the majority’ (Exodus 23:2). If the majority rules it is impure – it is impure, if the majority rules it is pure – it is pure.

אמר רב יהודה אמר רב אין מושיבין בסנהדרין אלא מי שיודע לטהר את השרץ מה"ת

Rav Yehuda says that Rav says: They place on the Sanhedrin only one who knows how to render a carcass of a creeping animal pure by Torah law. The judges on the Sanhedrin must be so skilled at logical reasoning that they could even produce a convincing argument that creeping animals, which the Torah states explicitly are ritually impure, are actually pure.

Why is it so important to be able to articulate positions contrary to your own?

Take hot button issues such as: abortion, war, immigration. This source is saying that you need to be able to articulate both positions convincingly.

What makes the Torah's approach unique?

(ב) וזה הענין מה שאמ' (סנהדרין י"ז.) אין מושיבין בסנהדרין אלא מי שיודע לטהר את השרץ וכו' ובתוס' הקשה מה לנו בחריפות של הבל וכו'. אך הפי' הוא כדי שיוכל ללמד זכות על מי שמתודה ואינו חוזר בו דאי' בגמ' (תענית ט"ז.) למה הוא דומה לאדם שתופס שרץ בידו שאפי' טובל וכו'

(Rabbi Tzadok HaKohen of Lublin

Composed: c.1845 - c.1895 CE)

This is to enculcate in a person the ability to see virtue even in someone who does wrong for the Gemara compares such a person to one who immerses in a ritual bath [to purify himself] yet holds a dead bug [which itself causes him ritual impurity]

How can you see virtue in the people who disagree with you most?

(יז) כָּל מַחֲלֹקֶת שֶׁהִיא לְשֵׁם שָׁמַיִם, סוֹפָהּ לְהִתְקַיֵּם. וְשֶׁאֵינָהּ לְשֵׁם שָׁמַיִם, אֵין סוֹפָהּ לְהִתְקַיֵּם. אֵיזוֹ הִיא מַחֲלֹקֶת שֶׁהִיא לְשֵׁם שָׁמַיִם, זוֹ מַחֲלֹקֶת הִלֵּל וְשַׁמַּאי. וְשֶׁאֵינָהּ לְשֵׁם שָׁמַיִם, זוֹ מַחֲלֹקֶת קֹרַח וְכָל עֲדָתוֹ:

(17) Every dispute that is for the sake of Heaven, will in the end endure; But one that is not for the sake of Heaven, will not endure. Which is the controversy that is for the sake of Heaven? Such was the controversy of Hillel and Shammai. And which is the controversy that is not for the sake of Heaven? Such was the controversy of Korah and all his congregation.

Meiri, Avot, Chapter 5 (1249-1310, France)
And which is the machleket (disagreement) thatis for the sake of Heaven?
Thatof Hillel and SHammai (100 bce), for one would rule on a matter and the other would disagree with him in order to understand the truth and not just for the sake ofprovocation or a desire to win.
... but that of Korah andhis congregation, they came tocomplain and Moses, our Teacher, mayhe rest in peace, about his leadership solely out of jealoust and provocation, in a desire to win