Episode Recap: The Devil's Advocate (1997)

Leadership Lessons from Satan's Master Plan

Jul 28, 2025

In this explosive episode of the Hard Knock University podcast, my co-host Seth Caples and repeat offender Chris Day joined me in the updated studio to dissect the 1997 thriller "The Devil's Advocate" through the unforgiving lens of leadership and project management. What we discovered was both brilliant and terrifying: Al Pacino's John Milton isn't just the devil… he's also one hell of a project manager. And that should scare the shit out of every leader out there.

TL;DR – Leadership & Project Management Lessons from The Devil’s Advocate (1997)

Q1: What leadership lessons can be learned from The Devil’s Advocate movie?
A: The film reveals how technical brilliance without ethics leads to destruction. Al Pacino’s character, John Milton, models high-level strategy, stakeholder management, and persuasion, yet uses those tools for manipulation. The core lesson: Leadership without morality is just control.

Q2: Is John Milton a good project manager in The Devil’s Advocate?
A: Disturbingly, yes. He scores high in scope, time, and communication management. He plays the long game flawlessly, builds systems that reward ambition, and tailors messaging for every stakeholder. But he fails at ethics, empathy, and emotional risk, making him a cautionary case study.

Q3: How does The Devil’s Advocate relate to real-world corporate culture?
A: Many of Milton’s manipulation tactics mirror toxic workplace behaviors: isolating high performers, promoting unhealthy competition, and ignoring long-term consequences for short-term wins. It’s a dramatized, hellfire version of dysfunctional leadership structures that actually exist.

Q4: What project management mistakes does Kevin Lomax make in The Devil’s Advocate?
A: He fails to manage scope (both professionally and personally) sacrificing his marriage and values for unchecked ambition. He lacks self-awareness and doesn’t set boundaries, leading to burnout and moral collapse.

Q5: What is the main leadership takeaway from The Devil’s Advocate?
A: Methodology without morality isn’t leadership… it’s manipulation. You can have all the tools and tactics, but if you lose your ethical foundation, your “success” becomes self-destructive.

Sharing this podcast might not save souls… but it might save someone’s next project!

THE PARADOX OF EVIL EXCELLENCE

Here's the uncomfortable truth that hit me like a freight train during our analysis: John Milton is arguably one of the most competent project managers I've ever seen portrayed on screen. This realization forced me to confront something I didn't want to admit; technical competence and moral bankruptcy can absolutely coexist in the same person, often to devastating effect.

I've spent years studying leadership failures, and Milton's approach to project management is methodical and sophisticated in ways that would make most Fortune 500 CEOs jealous. He identifies high-value targets, develops comprehensive long-term strategies, and executes with precision that I have to respect, even while it disgusts me. His recruitment of Kevin Lomax demonstrates masterful stakeholder analysis. He understands exactly what motivates his target and crafts an irresistible value proposition.

What makes Milton particularly dangerous as a leader is his ability to combine genuine strategic brilliance with complete moral flexibility. I've seen this combination destroy companies and lives. He understands human psychology at an expert level, knows how to build systems that reward the behavior he wants to see, and maintains unwavering focus on his ultimate objective across decades of planning. His communication skills are flawless. He tells people exactly what they need to hear, when they need to hear it, delivered with the perfect balance of charm and authority.

The chilling realization for me was that Milton's methods aren't entirely foreign to modern corporate culture. I've witnessed his manipulation tactics in real workplaces; isolating employees from outside influences, creating competitive environments that erode ethical boundaries, and rewarding short-term wins while ignoring long-term consequences. The difference is merely one of scale and ultimate intent.

This creates a challenge I wrestle with as someone who teaches leadership: how do we learn from Milton's undeniable competencies without adopting his moral framework? How do we distinguish between effective leadership techniques and manipulative exploitation? The answer I've come to is this; methodology without morality isn't leadership at all. It's just sophisticated manipulation dressed in a business suit.

THE DEVIL'S RESUME

Note: This résumé is not available on LinkedIn, but if it were, it would have endorsements from Machiavelli and Elon Musk.

After breaking down Milton's operation, I had to admit he'd built quite the empire. His hypothetical business plan reads like something from a top-tier consulting firm:

Company: Dominion Holdings International
Industry: Legal services, real estate development, corporate acquisition, and soul procurement
Mission Statement: Acquire, elevate, and control high-performing humans by maximizing their ambition, exploiting moral weaknesses, and removing all friction between desire and decision
Ultimate Goal: Create the Antichrist Exit Strategy: Eternal reign through systemic corruption

I mean, you've got to admire the clarity of vision, even if the vision makes you want to throw up.

PROJECT MANAGEMENT SCORECARD: RATING THE DEVIL

I scored Milton using my standard leadership and project management criteria, and the results were both impressive and terrifying.

Milton's Project Management Score: 4.5/5

For scope management, I gave him a perfect five. The guy knows exactly what he wants and never loses sight of the ultimate goal. His time management also earned a five. He masters the infinite long game with patience that spans decades. Most project managers I know can barely plan three months out.

Risk management got a four. He's excellent at minimizing exposure and maintaining plausible deniability, but he gets blindsided by emotional variables. That's what ultimately destroys his plan. He doesn't account for Kevin becoming unpredictable after losing his wife.

Communication earned him another five. He's a master manipulator who tells people exactly what they want to hear. I hate to admit it, but his persuasion skills are textbook perfect.

Stakeholder management dropped him to a three. He's great with everyone except his main target when things get messy. When Kevin starts cracking, Milton has no safety net, no backup plan for managing that relationship. This is what happens when leaders ignore feedback loops. If your only backup plan is ‘hope,’ you’re one bad sprint away from Milton-level meltdown.

Ethics got a negative 666, which is actually the industry standard for ‘burn it all down.’ Your ethics are the hidden secret weapon. Ignore them, and the project fails… guaranteed.

Milton's Leadership Score: 2.5/5

His vision scored a perfect five; world domination doesn't get clearer than that. Motivation also earned a five because he knows exactly how to trigger people's ambition and manipulate them accordingly.

But empathy? One out of five. He uses people without ever truly supporting them. Self-control got a two; he gets emotional when challenged and is blinded by his own pride. That ego is what kills him in the end.

Coaching and development earned a three. He builds successors but manipulates rather than mentors. There's no genuine development happening, just exploitation.

Humility scored a big fat zero. The guy literally brags that vanity is his favorite sin. That tells you everything you need to know about his leadership style.

Want to test your own leadership like we tested Milton’s? Use this scorecard on yourself (or your boss if you’re brave enough).

KEY LEADERSHIP LESSONS LEARNED

The movie's central theme hit me hard: free will is both a gift and a curse. As Milton states in his epic monologue, "I don't make anybody do anything." The greatest manipulators don't force decisions, they create conditions where people choose poorly on their own. I've seen this happen in my own projects when leadership set up incentive structures that rewarded the wrong behavior.

Kevin Lomax's downfall wasn't caused by external forces. It was his own unchecked ambition. Healthy drive becomes destructive obsession when ambition becomes self-serving and you stop caring about the people around you. I've made this mistake myself, and I've watched it destroy careers.

The scope creep lesson was particularly painful for me to watch. Kevin's inability to manage work-life balance led to the destruction of his marriage and ultimately his soul. I learned early in my career that scope creep doesn't just apply to contracts. It applies to personal life too. When you let the job bleed into everything else, disasters follow. Scope creep doesn’t just wreck your timelines. It will wreck your marriage, your sanity, and possibly get you recruited by Beelzebub Inc.

Milton's strategy of surrounding Kevin with enablers while isolating him from moral guidance reminded me why I always seek out people who will tell me when I'm being an idiot. Echo chambers are dangerous for any leader.

THE HARD KNOCK PHILOSOPHY CORNER

Chris Day brought some serious theological firepower to our discussion, diving deep into concepts that honestly made my brain hurt. He explored the plural nature of "Elohim" in Hebrew scriptures, the difference between monotheism and henotheism in ancient religions, and how original sin doctrine developed centuries after Christ.

His key insight stuck with me: "It's always your own decision that leads you to damnation." That's pure Hard Knock University philosophy right there. Own your choices, own your consequences.

BEHIND THE SCENES INTEL

Fun Facts That We Learned Along the Way:

Al Pacino initially turned down the role five times, thinking the script was too heavy-handed
Keanu Reeves took a $2 million pay cut to work with Pacino
The film was sued by sculptor Frederick Hart for copying his work
Donald Trump's actual penthouse was used for the billionaire's apartment scenes
Pacino improvised much of his famous "God is an absentee landlord" speech

THE BOTTOM LINE

The Devil's Advocate serves as a masterclass in both brilliant strategic planning and catastrophic leadership failure. Milton's tactical genius gets undone by his own ego. It’s a cautionary tale for any leader who thinks they're untouchable.

Here's what I want you to take away from this: own your mistakes when you make them. You're gonna make mistakes. You're gonna do the wrong thing. Nobody's perfect except for JC, and even he made mistakes when he was in the physical realm. Get over it, move on with your life, learn from it, and then teach other people about the mistakes you made so they don't have to make the same ones.

MISSION CONTINUES

The episode wrapped with a powerful reminder that while we may face temptation and make poor choices, redemption is always possible through acknowledging our mistakes, learning from them, and helping others avoid the same pitfalls.

Remember this: the devil's greatest trick isn't making you believe he doesn't exist. It's convincing you that your failures define you permanently. That's bullshit. Your failures are just tuition at the Hard Knock University. The devil wants you to think your worst mistake is the end of your story. It’s not. It’s the intro to your best chapter.

#HardKnockLesson:
Technical brilliance without moral backbone is just weaponized competence.
You can hit every milestone and still lose your soul. Build the kind of legacy you’d be proud to explain to your kid… or to St. Peter.

Drop a comment if you’ve ever had a “Milton” for a boss—or been one. We’re all friends here.