1/ Last year I read Moment magazine's Five Books Project ( https://momentmag.com/five-books-project/) - which asks prominent Tribespeople which 5 books are essential to be an educated Jew.

To put it mildly, this topic is right in my wheelhouse (book maven, rabbi, PhD in Jewish Studies)
2/ The basic question is: "which books I should read to be an 'educated Jew'" & it's variously interpreted. Initially, I was being cute: Bible, Babylonian Talmud, Jerusalem Talmud, Mishnah Torah, Shulchan Arukh.

But that's actually a poor answer.
3/ Ya see, I'm a book guy, but 80% of my vast library are reference books. I've read, cover-to-cover, 20% of my library (& 5%+ of my books I haven't even opened, oy)

The Moment shyla is abt reading, not owning. So for my 5 Books I needed to set real rules if I want to be useful
4/ I need to propose 5 books that are: (a) ones I've actually read & usually read often; (b) books I can expect everyone to be able to read before they're 30 yrs old; (c) and key: the basis for being educated no matter what stream of Judaism, from Reconstructionist to Chasidic
5/ Ya see, I can't expect everyone to read my original 5 (Talmud, Bible etc) because I personally had to force myself to read all of the Bible & did so only once. I took over 7 years to finish the Babylonian Talmud. And I don't ever expect to read all of the Shulchan Arukh.
6/ Those 5 books are basically reference; only the super-elite has read all 5 "books" (which is really over a 100 actual books) & in my own life, that's not what I re-read to make me educated and prepared to be the best servant of God I can be
7/ So I came up with my list last year & so far it's unchanged. These are 5 books (2 actual single books, 3 series) that I've read, that I can assign to ppl (& have done so for my conversion students) & I believe will be needed for every Jew from every form of secular & religious
8/ The Five:
(1) Rashi on Chumash
(2) Rabbi Menachem Leibtag's Chumash commentary
(3) Rambam's Laws of Repentance
(4) Kitov's "The Book of Our Heritage"
(5) Rav Soloveitchik's "Fate and Destiny"

See below for why.
9/ #1 Rashi on Chumash ( https://www.chabad.org/library/bible_cdo/aid/8165/showrashi/true)

This is the largest series, but most schools start this at the youngest age. While it looks cheap to basically add a 6th book (the Torah), it's also pretty much a given to know the Chumash.
10/ #1 cont: But my point is that knowing the parsha/Chumash isn't as needed as knowing Rashi's interpretation. Rashi's project is to choose one or two the paramount rabbinic comments on the verse out of the *hundreds* in the Gemara & many books of Midrash.
11/ It's usually wrong to claim 'Rashi says' b/c what we're quoting is a Gemara or Mechilta or Sifrei. Rashi's genius is choosing what he prefers. That's why other rabbis 'disagree' with Rashi - b/c they disagree w/ his choice or w/ his interpretation of the Chazal.
12/ This is also why choosing Rashi isn't being Ashkenaz-centric, b/c his commentary is just a collection of earlier sources. E.g., when Saadia Gaon sounds like Rashi, it's b/c Saadia is quoting the same Chazal.

Yet this popular misconception about Rashi shows his importance.
13/ I'm putting Rashi on the list, and as #1, b/c Rashi's comment on a verse is how the majority of Jews over our history have understood that verse. Rashi has become the baseline for how our people have primarily understood the Torah & as such knowing Rashi = knowing Chumash
14/ Knowing Rashi doesn't mean accepting the Midrash as the pure definition of the verse (for oh so many reasons) but IMO it's crucial for everyone to have a shared starting point, which has been Rashi (aka the rabbinic statements quoted by Rashi) for over a millennium
15/ It's also crucial to recognize that Jewish tradition rejects a literal translation of the Bible, and that also comes through when we read Rashi.

True, many people then take Rashi literally... but that's an easier theological/epistemological problem to deal with.
16/ That's the first of the 5:
*(1) Rashi on Chumash*
(2) Rabbi Menachem Leibtag's Chumash commentary
(3) Rambam's Laws of Repentance
(4) Kitov's "The Book of Our Heritage"
(5) Rav Soloveitchik's "Fate and Destiny"

In a moment, I'll add the next 2-5
17/ #2 Rabbi Leibtag on Chumash ( https://tanach.org/ ) feels like a cop-out b/c it's not even in a book yet (I'm trying! Send him an email to ask him to do it!) but it's 2020 & even suggesting 'books' feels outdated. Remember when we needed to say 'cordless' phone? 'Color' TV?
18/ Rabbi Menachem Leibtag (RML) has distilled the 20/21st Century work in 'pshat' commentary (esp. from Gush) & processes it through his own high quality pedagogy & clarity. While Rashi is needed as the baseline (even RML references it), every Jew needs to know the pshat.
19/ I taught Bible in Stern College for 3 years & I defined Pshat as the *necessary* interpretation of the Biblical text (as op. to "drash" which is a didactic interp., or at least a *possible* interp.)

Nobody has collected & taught the pshat on Chumash better than Rabbi Leibtag
20/ So since I believe an educated Jew needs to know the Chumash, my first 2 choices are #1 Rashi - to know what Jews over millennia, from the time of the Gemara until now, say about Chumash & #2 Leibtag - to know what the Chumash really means.
22/ Every student needed to spend at least one year living a Jewish life in a community, practicing the customs of the year, and I had them read Kitov to prepare for each season

Kitov is like Rashi for Jewish life & the holidays. In that, he teaches what traditional Jews "know"
23/ Kitov describes & explains the customs of the holidays, the laws, & the prominent midrashim.

He writes at a level for everyone to understand (see https://www.chabad.org/search/keyword_cdo/kid/11363/jewish/Kitov-Eliyahu.htm) as op. to Zevin's "Festivals in Halacha" which I love, but is more for elites
24/ These 3 books #1 Rashi on Chumash, #2 R'Menachem Leibtag on Chumash, #3 Kitov on the holidays are basically enough for every Jew to know how to understand God's covenant (the Chumash) as common custom (Rashi) & meaning (RML) & to understand Jewish life & the holidays (Kitov)
25/ The next two books are about philosophy, morality & life's mission:
#4 Rambam's Laws of Repentance
#5 Rav Soloveitchik's "Fate and Destiny"

Both are single books; but b/c they can be seen as specific to Orthodoxy, I need to substantiate the choices.
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