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Omar Jackson

@omarljackson

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What a great team, what a great city! 🩷 We’re humbled as we mark and name the faithfulness of God through this past year and hopeful as we turn our eyes with Spirit-filled expectancy toward what’s ahead in the next.

God is at work in Chicago and we’re are up for the adventure! Serving churches, training leaders, and working together to make Jesus visible in every neighborhood of Chicago.

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You caught the morning lineup. Now here’s round two. 👀

After you refuel at lunch, you’ll get a second shot to sit in a room that speaks directly to where you are right now. Same energy, new topics, another chance to walk away different.

We’ve got topics like shame , integrity, distraction, burnout, belonging. Pick your room. Saturday, August 22.

Comment CHICAGO and we’ll send you everything you need to register. 🔗

#chicago #legacy #legacydisciple #discipleship #disciple

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The rock star of my family, my nephew @omarljackson bringing the word this morning. Tune in to First Baptist Church South Hill! ❤️

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How should Christians think about race and identity from a theological standpoint?
It starts here: love does no harm to a neighbor. (Romans 13:10) And racism — at its core — is harm. It’s taking some characteristic of a person and using it to elevate yourself and push others down.
But the gospel forces a harder question — what insecurity inside of me needs that? Because when we make race or ethnicity an idol, we’re not just harming our neighbor. We’re violating the second commandment.
Our pathway is different. It’s pursuing flourishing together — every tribe, every tongue, every nation. Just like Jesus purchased. (Revelation 5:9)

#legacy #legacydisciple #lovethyneighbor

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Happy First Father’s Day to my boo 🤍

I see your sacrifices and I hope you know how deeply appreciated you are. Klay has an amazing Father to look up to as he grows and learns over the years what it means to be a man.

You are a present, kind, loving, loyal, hardworking man and I am so grateful for you. Happy First Father’s Day!! You are OVERLY deserving of this new title and we love youuu!! ♥️♥️♥️ #zdaddy #daddy

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The Prize is Christ!🙌🏻 Thank you to our brother, Omar, for preaching the Word with passion, and to Mr. Cruz for the Spanish recording.

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What a great endcap to this year’s Lead the City Conversations 2026 event series! 🙌 Big thanks to Chicago West Bible Church for hosting, Drew Hyun for sharing with us, and our sponsors—Wheaton College Graduate School, Crossway, Exponential, and The Chicagoland Collective—for helping make these gatherings possible and free for attendees.

We’re encouraged by what God is doing across Chicago and looking forward to summer! 😎

What topics or conversations would you like to see included in the 2027 Lead the City Conversations lineup? Share your ideas in the comments below.

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In this episode, Omar sits down with Esau McCaulley for a conversation that’s as thoughtful as it is formative.
Esau is a New Testament scholar, professor at Wheaton College, pastor, and contributing writer for the New York Times. His work often sits at and explores the intersection of faith, culture, and scholarship.

Together, they explore Esau’s faith rooted in the Black experience and how it shapes the way he reads the Bible and impacted his intellectual journey. Through metaphors they talk through the tension between experience and theology, and how our stories can both inform and challenge how we engage the text.

Diving into this beauty and complexity Esau shares how our perspectives can help us see things others miss, while also reminding us of the need to stay rooted in the truth of God’s Word.

This episode is an invitation to hold both the spiritual and the intellectual. To embrace mystery, pursue understanding, and remain anchored in a high view of Scripture.

If you’ve ever wrestled with how your story shapes your faith, or how culture and theology come together—this conversation is for you.

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I may be the one who sings and waves his arms around, but the other Jacksons have real star power, especially my nephew @omarljackson. Happy Birthday man. Keep leading the way! 🏆

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Chicago is a refuge of hope and encouragement🙌🏾

Spending time with @visionnehemiah, @heidimdye and the rest of the Legacy crew, reminded me just how simple and beautiful the Gospel really is. There’s a simplicity to seeing a problem, and being willing to pause your comfort to meet it. The way the Dyes love on their people (and strangers alike) is so deeply countercultural that it can only be evidence of the Gsopel at work.

I’ve genuinely never a seen a more missional, unselfish unit (and I know great people).They truly live their lives in constant accommodation of others, not for the sake of future gain or present glory, but out of humble and faithful obedience to Christ.

The last few months has been a serious wrestle with what ministry looks like as a young black woman outside of the formal theological institutions. It often feels like I am not just an anomaly, but a liability to the church.

In Chicago I was reminded that none of the identities that I’ve been taught to fear are central to the Great Commmission, because I am not called to make disciples of myself, but disciples of Christ. More than that, in spaces where caring for those in need is the Central mission, the question of who gets to help becomes way less important. For the first time in a long while, I wasn’t questioning if it was “my place to speak”….. If I was “allowed” to engage in the conversation, and I didn’t feel the pressure to be perfect to earn or justify my place. Something needed to be said, and I felt the freedom from both pride and shame, to just say it.

Ended the trip with a resisting the empire tour with @revdocmalc and @amishobaraka which genuinely felt like finding my people. Jesus was never a mascot for the Christian empire we’re all trying to build, He’s come to build a kingdom that dismantles the empire at its root…it’s a much greater investment (and that’s all imma say in that for now)

Sooo many sweet moments, tough conversations (and much needed silence)
Biggest takeaway was that I need to spend more time in Chicago🤷🏾‍♀️

See how I’m just sharing my life 👀 (I’m trying out here lol)

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Currently savoring this chapter and allowing it to unfold slowly. 5 months later…meet our sweet baby boy Klay 🙌🏽✨💙mama and dada are crazy about you mannn 🤪🫶🏽✨ We love you so much!

We asked God to order our steps and in this chapter, He gave us, you!!

💖✨Swipe to see (0-5months) ▶️⏩️

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