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Written by Leibel Estrin Reviewed by PO3 Michael Maman, USCG

When I first received orders to Astoria, Oregon in summer 2020, I already knew that the nearest Jewish community was two hours away. This would mark the first time I would be on my own without an in-person Jewish connection. Little did I know how much that would take a toll on me when I actually arrived and sought to incorporate Judaism into my everyday life.

Growing up in a traditional conservative household, our family embraced Jewish holidays, especially Shabbat every week. I enjoyed the Ashkenazic tradition from my mother’s side, and Sephardic from my father’s side. But synagogue attendance was rare, and I was never careful about following the mitzvot. I did not know how to follow the prayers in a basic siddur. Those were seen as luxuries I did not have time for. It was not until I entered USCG boot camp that I seriously considered incorporating Jewish practices into my everyday life. The shock and intensity of the training shook me so much I reached out to Hashem on a daily basis for spiritual strength to get through the day. I found myself saying the first paragraph of Birkat Hamazon silently after every meal, and taking free moments to recite Shemoneh Esrei when I could from a pocket siddur I brought with me. After boot camp, I left with a feeling of “Where do I go from here?” in terms of observance. I bought many books on prayer and faith to guide me along, and eventually, I got a basic idea on how to pray. Had I been given a copy of Leibel Estrin’s book Judaism from Above the Clouds upon arriving in Astoria, I am confident I would have been able to achieve my objective a lot sooner.

Judaism from Above the Clouds is a dense volume, but a quick read packed with insight. From the first few pages I knew this volume had a lot to offer. For example, the opening of the book discusses how the concept of “An eye for an eye, tooth for a tooth” (Exodus 21:24) is often misquoted. Noting that the same injury will affect people in different ways, Estrin points out that it is impossible to be taken literally. In Jewish circles most of us are familiar with the rabbinic interpretation of the verse to being about financial compensation. But Estrin raises the question: Why doesn’t the Torah just plainly say so? The response is profound in my opinion. Estrin writes, “We could easily miss the point. Compensating someone for damages could become as ordinary as buying milk. Therefore, the Torah stresses we should feel another person’s pain as if it were our own!” For me, that commentary adds so much more meaning to the verse than initial impressions, emphasizing the critical importance to de-escalate feelings of bitterness and hatred among people. We are each created unique in the image of the Divine and should, never resort to harming one another.

The book is structured as a crash course textbook in Judaism, beginning with the macro concepts of G-d, creation, man, Torah, and goes into the micro, or minute details of mitzvot, blessings, prayer, Shabbat, the Jewish Calendar, and Jewish Lifecycle. It’s all here, and nothing is left out. All of the prayers are discussed, and readers get a general sense of how a prayer service goes, which is helpful to someone like myself who never could follow the order in shul.

Each chapter has several footnotes for further clarification of ideas, as well as a “Words of Wisdom” section at the end of every chapter with insightful quotes and anecdotes, adding an additional layer of clarity for a given topic. Estrin makes sure to include as much depth as he can for each topic, while keeping chapters concise. For example, discussing the spiritual meanings behind the months on the Jewish calendar that we may not think about, and specific ways we celebrate that meaning in the holidays that occur during those months. For readers that are hungry for more knowledge, Estrin includes additional readings at the end of each chapter as well. Because each chapter is relatively short and reads fast, you can quickly go back to a topic of interest and find what you were looking for.

Additionally, Estrin incorporates concepts from Kabbalah and Chassidut to give deeper meaning and insight to each chapter. The exact parameters of Chassidut are not explained in depth, but Estrin calls it a “path to serving G-d.” Essentially it consists of teachings from the Hasidic movement, in the form of Torah commentary and Kabbalah making deeper meanings pertaining to G-d, the soul, and Torah more accessible to the layman in their service to G-d in everyday life. For example, in the chapter on Torah, Estrin cites the sages saying that there are five levels of the Torah, which are Pshat (simple meaning), Remez (allusion), Drush (homiletical interpretation), Sod (secrets of Torah), and Chassidut (path to serving G-d).

For someone unfamiliar with the Torah having different levels, you are immediately drawn in and want to learn more. An example of this breakdown is provided with the Modeh Ani prayer said in the morning upon waking up. The breakdown is fascinating to follow, but I think the Drush (Homiletical) explanation is my favorite. Estrin writes, “G-d faithfully returns to soul every morning, and does not withhold it for and debts we owe. So too, we should not withhold an article or our help for any ‘debts’ or other obligations that we may have made to others.” So the Drush message is one of forgiveness and starting anew for human relationships. Estrin says these five explanations can be
applied to the entire Torah, an amazing concept that opens up so many possibilities for exploration of various passages and prayers. The above is one of many examples of facets to Jewish thought that I was unaware of, despite my months of intensive self-study in Astoria with many Jewish volumes.

The section on blessings provides many insights as well. A list of morning blessings is given with their general meanings, but Estrin offers a footnote from Rebbetzin Chaya Teldon on the blessing, “Blessed are you Hashem for not making me a slave.” Apparently this blessing can be posed as a question daily, to say, “I may not be a slave, but have I liberated myself from being a slave to my desires, habits, and ways of thinking?” For almost two years I had recited that morning blessing daily and never thought of it on that deep level. It’s amazing how little tidbits can offer greater depth and understanding to something you have been doing for a while. The chapter closes with words of wisdom from Rabbi AJ Twerski on the Shehakol blessing for food and drink; that when early Chassidim would say the blessing, they would also have in mind things that deserve a blessing but never get one, such as music, joy, love, friendship, beauty, and so on. Again, a short and simple insight, but how easily can this be incorporated into daily blessings!

Judaism from Above the Clouds even goes beyond the intellectual and philosophical. In the Shabbat chapter, a tasty Challah recipe from Spice and Spirit cookbook is given. The appendix has lots more to check out, including the five levels of the soul, and an overview of the chain of scholarship in Judaism, starting from Moses until codified Jewish law.

My three minor criticisms are that first, that the book is written from the Ashkenazic perspective, so customs from the Sephardic, Mizrahi, or Yeminite traditions are not discussed when it comes to prayers, food, or the holidays. Also, all of the Hebrew in the book is transliterated. It would have been nice to see a side by side Hebrew text of the prayers or blessings with the transliteration followed by the English translation. Additionally, the front tagline reads “A Handbook for the Wondering Jew,” but on the back cover summary it says the book was written for people who want to know more about Judaism. So the book’s audience needs to be clarified whether it is just for Jews or the public at large.

The book serves as an intellectual crash course in Judaism as well as a basic overview of how to pray and being more spiritually aware. There are insights to pick up no matter your level of observance, and Estrin writes that becoming observant is a process, not an “all or nothing” approach. In that sense, I think Judaism From Above the Clouds can serve for both Jews and wider audiences. As stated previously, if I’d had a copy of this book in August 2020, I would have been much more versed in Judaism on a philosophical and practical level. I highly recommend the Aleph Institute to consider publishing a version for all Jewish US service members that they can carry with them to reference when needed

Originally published in the Shavuos 2022 issue of The Jewish American Warrior.