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Rabbi Ya’akov Trump serves as the Rabbi of the vibrant community of the Young Israel of Lawrence Cedarhurst. Part of his mission is to share his passion for the Torah and its relevance in contemporary times. His innovation has led to numerous engaging programs in his community and beyond. He is a featured speaker on YUTorah.org, has his own Nach Yomi website, has produced a number of podcasts including Nach Yomi, Aliya Yomi and Epilogues. He recently released an App on both the App Store and Google Play. He is the on the executive board of the RCA as vice president for the New York area. He was listed in the City and State magazine in the Faith 100 of 2023. He was also nominated for the Marquis Who’s Who of America 2023 volume. Rabbi Trump is a current fellow at the Krauthammer Fellowship of 2023-24 with the Tikvah Fund. Rabbi Trump sits on the board of the Vaad of the Five Towns and Far Rockway.

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Check latest episodes from Rabbi Trump podcast

Hidden Figures on Sukkos

2026/09/23

Which figures from our past stand behind the festivals, and how do their legacies shape the closing days of Sukkos? Drawing on the Tur, the Sfas Emes, and the teachings of Ohr Gedaliahu, this shiur explores the Avos, Dovid HaMelech, and Moshe Rabbeinu in relation to Sukkos, Hoshana Rabba, and Shemini Atzeres. The sources uncover the power of simple prayer and the shared inheritance that binds every Jew to Torah.

Two Clouds

2026/09/23

If Sukkos commemorates the clouds that accompanied us out of Egypt, why do we celebrate it in Tishrei? This shiur examines the Vilna Gaon's teaching alongside sources that distinguish the cloud of guidance from a cloud of spiritual illumination. That distinction opens a deeper understanding of what was lost after the Golden Calf and what the return of the clouds means for Sukkos.

The Sukkos Triangle

2026/09/23

What connects the shelters Yaakov built, the first stop after the Exodus, and the sukkah we enter each year? Following the parallels between these three appearances of Sukkos, this shiur explores the first night of freedom as a leap of faith met by Hashem's protection. It offers a fresh understanding of the relationship between Pesach and Sukkos, and why we revisit our vulnerability precisely at the season of the harvest.

Stars and Raindrops

2026/09/23

How much of the sky should a sukkah let in? Beginning with the halachos of stars, sunlight, and rain passing through the schach, this shiur explores the balance between shelter and openness to Hashem. It connects that openness to the renewed relationship with Hashem after Yom Kippur and the special joy of Sukkos.

Festival of Water

2026/09/23

Why does water play such a central role in the celebration of Sukkos? Through the water libation, the prayers for rain, and the Midrash of the “weeping waters,” this shiur explores the longing of the earthly world to draw close to its Creator. These sources reveal how Sukkos turns dependence on water into an expression of yearning, reunion, and joy.

The Whys of Judaism - Yomim Noraim

2026/09/08

This is a source based compilation of "why" questions covering the Elul through Yom Kippur cycle, moving from Erev Rosh Chodesh fasting and shofar blowing in Elul, through Selichos customs, Rosh Hashana practices (simanim, 100 blasts, Tashlich), the Aseres Yemei Teshuva, and the Yom Kippur liturgy from Kol Nidrei to Neilah.

Journey through Nach - Shoftim 18: The Shrine Heist

2026/09/08

Shoftim 18 opens with five Danite scouts who lodge at Micha's house, recognize the voice of his Levite priest, and ask him for a sign before heading north to Layish, a quiet and isolated city they report back as easy prey. Six hundred armed men then return, strip the shrine of its pesel, ephod and terafim, poach the priest with the offer of serving a whole tribe instead of one household, and leave Micha asking what he has left now that his god and his kohen are gone, after which they destroy Layish and rebuild it as Dan. The shiur presses the question of who the heroes are and concludes there are none, since the only innocent party is the Sidonian population of Layish, and it closes with the dispute of Ralbag, Radak and Rashi over how long the pesel of Micha stood in Dan, from the era of Yavin, to the exile of the aron at the end of Eli's life, to the exile under Sancheriv.

Embracing Inconvenience

2026/09/03

Why does the Torah sometimes demand the harder path when an easier one would achieve the same result? Drawing on the Meshech Chochma's insight into Sukkah, Rivkah's kindness at the well, the principle of mitzvah bo yoter mibshlucho, and Tim Wu's essay "The Tyranny of Convenience," this shiur explores when Judaism asks us to resist the pull of ease. In a world where convenience decides everything, discover how embracing friction builds character, deepens relationships, and shapes who we become.

Am I always in the middle? A guide for the Yemei Ratzon

2026/09/03

What does it actually mean to be a beinoni, the person whose fate hangs suspended between Rosh Hashana and Yom Kippur? Starting from the Gemara in Rosh Hashana 16b and the Rambam's formulation in Hilchos Teshuva, this shiur works through two core questions: why is standing still spiritually so dangerous, and how can anyone's merits and sins truly balance out when the law of averages says a perfect tie is nearly impossible? Answers from the Lechem Mishna, the Alter of Novardok, Pachad Yitzchak, and Nesivos Shalom reveal that the scales measure character rather than a tally of deeds, and that teshuva itself is what tips them

Journey through Nach - Shoftim 17: The Shrine of Micha

2026/08/28

Micha creates a private shrine containing an idol, sacred objects, and a priest, revealing the spiritual confusion of Israel during the era of the Judges. When a wandering Levite arrives, Micha hires him as his personal priest and treats his presence as a guarantee of divine favor. The story illustrates how people can reshape religious practice around personal desires while convincing themselves that God approves.

All or Nothing

2026/08/28

Examining how high to set the bar for goals in life. The higher we set them, the more likely some will excel but the fewer people will hit them. We will examine this from through the models of Chanukah, Sefiras Haomer, fasting, Tefilah and Emunah.

Journey through Nach - Shoftim 16: The Fall of Shimshon

2026/07/30

This episode explores the tragic downfall of Shimshon as his relationship with Delilah leads him to reveal the secret of his strength and fall into the hands of the Pelishtim. Drawing on classical sources, it examines Shimshon’s spiritual decline, the consequences of his choices, and the deeper meaning of his blindness and captivity. The story concludes with Shimshon’s final act of courage and sacrifice, through which he strikes a devastating blow against Israel’s enemies.

Whys of Judaism - Jew and the World

2026/07/21

This session explores some of the most common questions people ask about Orthodox Jewish life and practice, including the yarmulke, head coverings, handshaking, modest dress, Shabbos observance, Hatzalah, organ donation, and Jewish involvement in society. Drawing on the Talmud, halachic sources, and historical context, Rabbi Yaakov Trump explains not only what these practices are, but the ideas and values that shaped them. This shiur is part of the Why's of Judaism series, which uncovers the reasoning and meaning behind Jewish beliefs and observances through classical Torah sources and practical contemporary applications.

Journey through Nach - Shoftim 15: Widening Gyre of Revenge

2026/07/21

Shoftim 15 traces the widening cycle of betrayal and revenge as Shimshon burns the Philistine crops, retaliates against their violence, and is ultimately handed over by the fearful men of Yehuda. The shiur explores the symbolism of the foxes, the halachic and moral questions surrounding Shimshon’s surrender, and his miraculous victory with the jawbone of a donkey. It concludes by examining Shimshon’s complicated emergence as a leader whose deliverance of Israel remains powerful but incomplete.

Why's of Judasim - Blessings

2026/07/19

This installment of The Whys of Judaism explores the world of blessings, asking why Judaism insists that we pause and acknowledge God before enjoying anything in this world. It traces how brachos evolved from spontaneous personal expressions into the standardized formulas we know today, and explains the logic behind their many varieties, from blessings on food and mitzvos to blessings of praise and wonder. Along the way it tackles curious questions, such as why there is no blessing on giving charity, why we say 100 blessings a day, why we remove the knife before Birkas Hamazon, and why Ashkenazim and Sephardim differ on the besamim blessing at Havdalah.