Gary Sheng & David Kobrosky - Yom Kippur Theological Dialogue

Divine Connection on Yom Kippur

The Nudge

David opens explaining his outreach: "I just had this like, you know, it kept coming up like a couple times last night... Gary Sheng."

Gary's interpretation: "I just have to imagine it was God that made you reach out especially on a holy... I think so."

David confirms exclusivity: "There's no one else I'm messaging. I'm messaging you... It was just your name. Just you. It wasn't the new Intros feature."

Gary's Baptism and Healing Ministry

Upcoming Baptism

Gary shares major news: "I'm going to get baptized this weekend."

David's response: "Oh, wow. That's a big deal... Congratulations."

The Healing Pastor

Gary describes finding a pastor he respects: "He's highly favored... He has helped the blind see, the deaf hear... apparently thousands of cases."

Character description: "He's like the most humble dude who literally just... All he does is respond to nudges from God."

Theological grounding: "His theology is that like you can't just randomly heal people. God needs to basically be the one that's doing it. You're the vessel."

Most extraordinary claim: "He said he's raised people from the dead."

Divine Introduction Story

Gary explains how he met this pastor through Brenda Gentry: "In March this pastor, he was praying one day then the name Brenda Gentry came into his mind."

The journey: "He drives up, there's all kinds of issues that happen on the way... that's often called spiritual warfare. All kinds of things about the car wasn't working... the car was stolen."

Portal experience: "He literally saw a portal open to heaven... an extreme atmosphere of holiness."

Gary's Eye Healing

Personal testimony: "He healed my eyes. It's not perfect. But my eyes are actually... I can see further than I used to."

Faith test: "They found glasses after I left that venue... But I was like, no, I want to have faith that this healing actually will work."

Result: "I think it's sufficient for driving without glasses now."

Israel and Jewish People Theology

Gary's Repentance

Major confession: "What I repented for a few days ago like a week ago was having negative feelings towards Jews."

Recognition: "It was just like a realization that I have to be a lot more careful about the content that I'm consuming because... how hostile it's become against Jews."

Biblical Understanding of Chosen People

Gary's evolved view: "The Jewish people are chosen... Christians when they're seeing things clearly, they are out of God's love for all humanity. We are being grafted into the greatest story ever told."

On replacement theology: "The church is not Israel in the Bible."

Covenant faithfulness: "God created a covenant with the Jewish people... Our God is a faithful God meaning... covenant meaning contract... Our God Yahweh is a God that does not forget the promises that he makes."

Prophecy About Jewish Conversion

Gary shares biblical scholarship: "Really really smart Bible scholar Christian Bible scholars are like God prophesied that the Jewish people would be among the last to convert."

The remnant: "When it happens, it really happens and it will happen through a small remnant of 144,000 people."

End times significance: "This all then marks the... end times where a bunch of things happen."

Theological Institutions Critique

Catholic Church Analysis

Gary's assessment: "I have advised and probably will continue to have a toe with the Vatican... I did not sense holiness in that structure."

Vatican politics: "What I was privy to was cardinals framing different cardinals for different things."

Conspiracy mention: "People say that you have to sacrifice a child to even be in the running to actually be picked for [Pope]."

Candace Owens and Anti-Semitism

Gary warns: "Candace Owens is a converted Catholic... She has one of the largest anti-Semitic YouTube channels... she has seven million [subscribers]."

Content description: "It's just like constantly like the Jews did it, the Jews killed Charlie Kirk."

David's AIPAC Experience

Youth Lobbyist at 15

David's teenage motivation: "I was 15. I didn't give a shit. I was just like... I just wanted to meet girls."

Activities: "They would fly me to DC and I'd like talk to like... four or five senators about like why Israel's important for the America relationship."

Witnessing Big Money

Donor event story: "This wife next to me of like some rich old Jewish guy looks to him. He's like hey, honey, I kind of want to go to the middle section for the nicer meal. And he looks at her, he goes, okay. Writes me a fifty thousand dollar check."

David's shock: "I'm like what? Are you serious? That's real money."

Realistic View of Lobbying

David's assessment: "I don't think it's a big conspiracy. I think it's pretty clear... It's very transparent. They're like hey we want your money, this is important."

AIPAC strategy: "They aggregate a lot of rich people... They organize sessions and they're really adamant about setting up meetings with as many of the senators."

Uncomfortable Truths Discussion

Old Testament Violence

Gary raises difficult topic: "There's a lot of cases in the Old Testament of God telling the Israelites to mass murder entire tribes."

Political reality: "I can see why Netanyahu would have to be lying a lot... because of the secular real political dynamics."

Gaza Situation Analysis

Gary's empathy: "If I'm a Gazan boy, I grew up to a military age, I'm gonna kill as many Jews as possible."

Rehabilitation question: "How can they be rehabilitated after what has been done to them?"

Ethnic cleansing reality: "If every single person that you let grow up into that age is a liability to your family..."

Islam as Conquest Religion

Gary's analysis: "Islam is a religion of conquest, forced conversion... and real politic."

Contrast with Christianity: "This is different from Jesus saying render unto Caesar what is Caesar's... be peaceful... but also true to your faith."

Dearborn, Michigan Example

Cultural takeover: "On like these big loud speakers at 5:30 a.m. there's like these Muslim prayer sounds... in Dearborn, Michigan."

Pattern recognition: "That is just a small microcosm of what happens when Muslims take over a municipality. They take it over, they make it so that it's insufferable to live your own life."

Torah as Compressed Wisdom

Gary's Insight

Revolutionary framing: "What the Old Testament, what the Torah was, was a hyper compressed history and wisdom about how to live your life in a way that God would find pleasing."

David's response: "That's a great way to put it. I've never thought of it that way. But I think that's the best description I've heard of it."

Memory and Transmission

Why poetry and songs: "Why is it helpful, David, to record wisdom about how God's universe works in poetry, in Psalms? Why David? Because it's easier to remember songs."

Pre-printing press reality: "When you're just not able to carry around a whole encyclopedia because you're always like on the move."

David's Worldview and Response

Current Spiritual Status

David's position: "I'm Jewish. Culturally mainly. I think it's... It feels good. It's like part of my family."

On conversion: "I don't see myself converting. I don't have any like... I'm kind of more in the process of forming my own worldview."

God's place: "I think God's probably a part of it but I think there's other more tangible parts of it."

Intellectual Framework

Kyle Harrison influence: "Your religion you're a part of... should be like a lagging indicator of your values not like a leading one... You should figure out what you believe or have principles and then kind of determine where you belong, not join a group and then adopt your principles to that group."

Logical consistency requirement: "Worldview has to be a logically consistent... to respect your own intelligence."

Advice to Gary

Cautious wisdom: "The thing I would caution against as a friend is just like... if you're going to commit to something make sure it's really is as rationally sound as possible."

Recognition of Gary's importance: "You're an important thinker in the world... very few spiritual thing... you're a rare thinker... Maybe you're a form of a prophet."

Israel-Palestine Views

David's Nuanced Position

Current concerns: "What's going on in Israel is absolutely terrible... especially the food thing... it's really fucked up."

Self-destruction worry: "The reason Israel doesn't exist in 50 years from now is because we keep going down this path."

Reform advocacy: "The pro-Israel move right now should be to... reform Israel probably."

Moral lines: "There's a lot of stuff I'm like there's no argument for this. There's just no... aside from power grabs."

Gary's Evolution

From simplicity to complexity: "Even though previous part of me wanted that simple answer [genocide narrative]... it's about really seeking the truth."

Individual calling: "Maybe God wants you to do that [support Israel financially]. But maybe God just wants you to be a good mother or father or build that community tech startup."

Yom Kippur Reflection

David's Tradition

Surfing for reflection: "I remember I surfed one year probably 10 years ago... I remember being on the water just me and my surfboard... I had some really reflective moments."

Breaking routine: "It was such a break in my typical schedule that it kind of like opened my mind up a little bit."

Significance of the Day

David's gratitude: "When I look back in a couple years from now it'll be like oh I talked to Gary. I got to [talk with] Gary Sheng for an hour on his thoughts about religion and Judaism."

Temple equivalent: "I feel like this was my equivalent of going to temple today. So thank you."

Individual Calling and Free Will

Gary's Understanding

Divine script: "God gives each of us individual callings and is like the script writer for the most amazing story ever written with tons of plot twists."

Opposite sides casting: "I think he sometimes casts two people that are superficially on opposite sides as well."

True Christianity

Heart transformation requirement: "You only have really come into the faith when you have... Your heart has completely changed... You have emptied yourself completely of your will and replaced it for God's will."

Love with truth: "You have deep love for your fellow man while being truthful about uncomfortable truths."

Denominational Independence

Gary's approach: "Why I've not jumped into joining some kind of denominations because I think when you join a denomination you stop interrogating these truths super seriously and you delegate all your thinking to priests, to bishops, to Pope."

Numbers game problem: "When you're trying to get your numbers up you're often making mental shortcuts... being a politician... what does the base want me to say versus what does God want me to believe."

Final Exchanges

Gary's Blessing

On conversion: "If it is meant to be you will have the exact experiences that you need to make it all make sense to you."

Gratitude: "I feel privileged that you reached out to me on this holy day to just have a conversation about where my head has been."

David's Journey

Commitment to truth: "I think it's wherever the truth takes you... It has to be a logically consistent worldview."

Morning practice: "I've spent a lot of time writing most mornings recently about this... how the world works and discovering how the world works."

Open path: "I'm gonna keep on that journey... I'll go where the world takes me."

Key Themes

1. Divine Orchestration: David's Yom Kippur nudge interpreted as God-ordained connection
2. Theological Wrestling: Gary's journey from anti-Jewish sentiment to understanding chosen people theology
3. Uncomfortable Truths: Frank discussion of ethnic conflict, Old Testament violence, Islamic conquest
4. Institutional Critique: Skepticism of Catholic Church and denominational thinking
5. Logical Consistency: David's emphasis on worldview that respects intelligence
6. Individual Calling: God's unique path for each person beyond political positions
7. Truth Seeking: Both committed to following truth wherever it leads
8. Cultural vs. Religious Identity: David's secular Jewish identity alongside spiritual openness

This conversation represents a profound theological dialogue between a newly zealous Christian convert and a culturally Jewish secular thinker, sparked by what Gary interprets as divine intervention on Judaism's holiest day. The discussion navigates complex territories of Israel-Palestine, chosen people theology, uncomfortable biblical truths, and the nature of genuine faith while maintaining mutual respect and intellectual honesty.