kosher bookworm

Entering the gates of teshuva


It is that time of year, a moment of intense retrospection, of looking inward to pave the way for teshuva, to perform the intense process of repentance from deeds that were of questionable spiritual value. Teshuva, to repent, is one of the most intense and important deeds for the Jewish people to engage in.

With this in mind, and in preparation for the upcoming High Holidays, I would like to bring to your attention a new work based upon the classic work on teshuva, “Shaarei Teshuva,” by Rabbeinu Yonah of Gerona. 

Last year we witnessed the publication by Artscroll of a detailed translation and commentary on this classic. This year, a new volume on this classic, a commentary with contemporary themes and convincing methodology was recently released in Jerusalem timed and themed for this holiday season.

“Opening The Gates of Teshuva: A Contemporary Commentary on Rabbeinu Yona’s Shaarei Teshuva” (Adir Press) by Rabbi Asher Baruch Wegbreit of Yeshiva Bircas HaTorah in Jerusalem, was compiled to give the modern Jewish reader a comprehensive thematic understanding of our sages teachings as a useful and practical tool for to the enhancement of one’s commitment to Teshuva.

As has been my want, I will now give the author the opportunity to present his take on his method for your edification. 

Please read Rabbi Wegbreit’s teachings carefully. His case in expressing the need for a modern commentary on Shaarei Teshuva in my opinion is most compelling:

“No one can deny that Shaarei Teshuva is one of the most important texts in Jewish history. Other than the Rambam’s Hilchos Teshuva, Shaarei Teshuva arguably stands alone as a guide and source of inspiration for the profoundly important mitzvah of teshuva.”

This brief introduction leads the rabbi to relate to us further both his method and purpose:

“I resolved to provide an English commentary that is based on some of the highly regarded commentaries available in Hebrew. These include the recent classic Zeh HaShaar by Rav Benyamin Zilber; Shaarei Teshuva HaMevo’ar by Rav Modechai Zuckerman; and a recent work by the noted baal mussar Rav Eliahu Rote entitled Shaarei Teshuva HaMeforash. These works bring out myriad deep and masterful insights in Rabbeinu Yonah’s work.

“In addition, I felt that there was another compelling reason to attempt a contemporary version of this classic work: I was concerned that the relevance of this text to our lives — and our obligation of yiras Hashem, the mitzvah to fear G-d — can be lost in a mere translation into English. This is due to the perceived fragility of our generation. Many great rabbis have cautioned against placing too much emphasis on the topic of ‘fear of punishment.’

Therefore, a modern-day reader who reads Shaarei Teshuva may be afraid to focus on what appears to be a great deal of ‘fire and brimstone’.”

Rabbi Wegbreit’s basic motive and theme in writing this sefer can be summed up in the following phrase:

“Rendering fear of Hashem accessible to our generation,” that being that when teaching belief, emunah, we must be clear in our teachings in basic, clearly explained language as to what G-d expects from us, at all times.

“Recognizing the power contained in this work, I attempted to distill Rabbeinu Yonah’s insights in a way that demonstrates how we can reframe our perspective in favor of the life — enhancing view of the Torah. We can attempt to absorb the true outlook concerning good and evil. 

“In addition, I provided many practical exercises to enable the reader to experience Shaarei Teshuva as a guidebook, transforming the concept of complete teshuva from something out of reach to something feasible. My goal is to empower every Jew with the ability to do teshuva that ascends to the Throne of Glory.”

To say that this work is different from other works on teshuva would be a gross understatement. We live in both dangerous and most difficult of times. Our faith makes many demands upon us. Both our life style and our religious obligations mandate many obligations that could prove to be most daunting to the average adherent of our faith.

Giving our fellow Jews both deep purpose and convincing reason to adhere to the words of and commands by G-d require deep teaching methods and sincere purpose of faith. Anything less could lead to a failure in the success of doing true and successful teshuva at this most sacred time of year.

Rabbi Wegbreit, in his method of presentment gives us the answer to our quest for spiritual success.


Last year we experienced the teachings of Rabbi Immanuel Bernstein from his excellent sefer, “Teshuvah” (Mosaica Press). If you already have it, do reread it. If you do not have a copy, I strongly urge you to buy one. 

Also, Far Rockaway’s Rabbi Yechiel Yitzchok Perr’s excellent anthology of teachings, “Mind Over Man: The Climb to Greatness” (Israel Bookshop), adopted by Rabbi Yehuda Keilson, will provide you with a series of excellent teachings that will further add to the spiritual quality of the upcoming holidays.

And, lastly for this week, please consider Woodmere’s Rabbi Yanki Tauber’s volume two, “Inside Time: Rosh Hashanah to Purim” (Meaningful Life Center) as an excellent source of short teachings for this holiday season and beyond.

In the meantime may I take this opportunity to wish you, my dear readers, a heartfelt ketiva v’chatima tovah.