Cover image of show The Awkward Pastor

The Awkward Pastor

Podcast by Brandon Estep and Tim Waybright

English

History & religion

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About The Awkward Pastor

The Awkward Pastor is a savage Christian podcast for people exhausted by fake religion, shallow answers, and plastic faith. Hosted by Brandon—a pastor and Iraq war combat vet—and Tim, a seasoned believer with real ministry scars, this show confronts chaos with biblical truth, satire, and zero concern for religious comfort. From grace for the worst sinners to exposing church hypocrisy, nothing is off-limits. If you’re tired, skeptical, or done pretending—hit play.

All episodes

24 episodes

episode (Ep. #22) The Night Everything Changed: The Story of Jon Holt artwork

(Ep. #22) The Night Everything Changed: The Story of Jon Holt

What happens when a man survives the kind of night that should’ve killed him? In this powerful episode of The Awkward Pastor, we sit down with Jon Holt — an Iraq War veteran that Brandon served with, Purple Heart recipient, and law enforcement officer whose story sounds more like a movie than real life. After surviving a devastating EFP roadside bomb attack in Iraq that killed two of his brothers-in-arms and left him severely wounded, Jon was told he may never walk normally again. But that wasn’t the end of his story. It was the beginning. By the grace of God, Jon went from the battlefields of Iraq to a life spent serving and rescuing others as a police officer — pulling people from burning homes, responding to horrific crashes, and walking through trauma most people could never imagine. His journey is one of pain, resilience, brotherhood, faith, survival, and purpose. This episode dives deep into: * The reality of combat trauma and PTSD * Survivor’s guilt and grief after war * Brotherhood forged in combat * The mental and emotional cost of law enforcement * Faith in the middle of suffering * How God can bring purpose out of devastation * Overcoming impossible odds * Redemption, resilience, and hope after pain This is not a polished Hollywood war story. It’s raw.It’s human. And it’s unforgettable.

14 May 2026 - 2 h 3 min
episode (Ep. #21) If Your Gospel Requires Your Help...It's Fake artwork

(Ep. #21) If Your Gospel Requires Your Help...It's Fake

What if the most dangerous false gospel isn’t outside the church…but sounds almost exactly like the truth? In this episode of The Awkward Pastor, we expose the “Jesus + something” gospel...a subtle, soul-crushing lie that started with the Judaizers and still shows up in churches, sermons, and social media feeds today. They didn’t reject Jesus. They just made Him… insufficient. “Jesus saves you… but you better perform.” “Grace starts it… but you better maintain it.” “Faith matters… but your effort proves everything.” It sounds spiritual.It sounds serious.It sounds right. But it’s poison. In this episode, we break down: What the Judaizers were really teaching (and why it spread so easily) * Why adding anything to the gospel doesn’t strengthen it—it destroys it * How performance-based Christianity quietly replaces peace with pressure * The difference between real obedience and religious exhaustion * How to finally rest in a gospel that doesn’t depend on you If your faith has ever felt like a constant test you’re failing… If you’ve been stuck trying to prove something God already settled… If Christianity feels more like a burden than freedom… This episode is going to hit you right where you live.

29 Apr 2026 - 1 h 10 min
episode (Ep. #20) Why Did Jesus Have To Die? (The Cross Explained) artwork

(Ep. #20) Why Did Jesus Have To Die? (The Cross Explained)

With Good Friday approaching, we’re forced to confront a question most people avoid—why did Jesus have to die? The cross of Jesus Christ is the center of the Christian gospel. Without His death and resurrection, there is no forgiveness, no peace with God, and no hope of salvation. But if God is good, why didn’t He simply forgive sin and move on? Why the cross? Why did Jesus have to be crucified? In this episode of The Awkward Pastor, we go deep into the why behind the cross—exploring God’s holiness, justice, and mercy, and what was really happening when darkness fell and the earth shook. We also examine the supernatural events surrounding the crucifixion and unpack the powerful symbolism behind them, revealing that the cross was not just an execution, but a divine act of redemption. Joining us is A.T. Stewart, a seasoned Bible expositor, and former pastor with over 50 years of ministry experience bringing clarity, depth, and biblical truth to one of the most important questions in Christianity. Check out Dr. Stewart's sermons here: https://podcasts.apple.com/us/podcast/a-t-stewart-ministries/id82454198

25 Mar 2026 - 1 h 8 min
episode (Ep. #19) When The Phone Rings at 2AM: Dealing with Tragedy artwork

(Ep. #19) When The Phone Rings at 2AM: Dealing with Tragedy

Tragedy is something every person will face eventually. A sudden death. A devastating accident. Suicide. Violence. Loss that makes no sense. In this episode, Brandon and Tim step into an honest, raw conversation about tragedy in a broken world. This episode was motivated by the recent sudden and tragic death of Brandon’s close friend, which forced a deeper reflection on questions many people wrestle with but rarely say out loud: Why does tragedy happen? Where is God in the middle of it all? With biblical truth, real-life experience, and the occasional dark humor that life sometimes requires, Brandon and Tim talk openly about the reality of living in a fallen world while still holding on to hope. In this episode, they discuss: • Why tragedy exists in a broken world • Why suffering and loss are part of the human experience • How hope and meaning can still emerge from painful moments This conversation isn’t about giving easy answers or pretending tragedy is simple. It’s about facing the hard realities of life with honesty, faith, and the kind of discussion that happens when friends sit down and talk about the things that actually matter. If you’ve ever struggled to understand suffering, wrestled with grief, or wondered how faith survives real-life tragedy, this episode is for you. Because sometimes the most honest conversations about faith begin in the darkest moments.

11 Mar 2026 - 1 h 10 min
episode (Ep. #18) We Got A Letter from Son of Sam (Live) artwork

(Ep. #18) We Got A Letter from Son of Sam (Live)

We went live with Investigator Eric Smith (featured in our previous episode series “Serial Killers That Received Christ”) to talk about one of the most controversial questions in true crime and Christianity: 👉 Can a serial killer truly be saved? After those episodes, we reached out to David Berkowitz...also known as the “Son of Sam.” He wrote us back. In this episode, we read his letter live and wrestle with what it means for the power of the Gospel to transform even the darkest lives. But this didn’t stay theoretical. This live stream turned into a powerful moment of conviction and response ending in a clear Gospel presentation and an altar call for anyone ready to stop playing games and come to Christ. This isn’t about sensational true crime...it’s about whether we actually believe the Gospel is powerful enough to save anyone...and we do.

18 Feb 2026 - 56 min
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