Summary
This article examines how human behavior under pressure—described in Robert Greene’s The 33 Strategies of War—mirrors the four biggest mistakes defendants make during a federal investigation: silence, excuses, inconsistency, and delay. Using lessons from Aristotle’s Golden Mean, Wonka’s characters, and real Presentence Report examples, I explain why defendants often lose years not because of the crime but because of how they respond afterward. This long-form guide helps readers understand stakeholder expectations and what they can begin doing today to influence their sentencing outcome.
Table of Contents
Where This Started
Why Greene Applies to Sentencing
Foundation One: Silence
Foundation Two: Excuses
Foundation Three: Inconsistency
Foundation Four: Delay
The Real Connection
What You Can Do Today
FAQ
Resources & Links
About the Author
Call to Action
Where This Started
While traveling back from Northern California last week, I finished Robert Greene’s The 33 Strategies of War. And I’ll be transparent: I tried to read the book without applying it to sentencing or prison — but apparently I’m just not normal.
At this point, I’m not changing or fixing it. I’m not sure what to do other than embrace it. The truth is, I can’t read a book without dragging it into something related to a government investigation. Every book becomes the same lesson.
A few days ago, I was reading Willy Wonka and the Chocolate Factory with my son, Jason. Most dads would read it, share a few thoughts, and move on. Instead, I somehow turned Augustus Gloop’s behavior into a conversation about Aristotle’s Golden Mean — the idea that the good life sits in the middle between two extremes:
- cowardice on one end, recklessness on the other — courage in the middle
- stinginess on one end, wastefulness on the other — generosity in the middle
- passivity on one end, obsession on the other — balanced discipline in the middle
Augustus Gloop, I told my son, lives nowhere near the Golden Mean. He lives in the “you’re going to regret this any second now” part of the chart.
As I continued this lesson on Aristotle, comparing it to a fictional child drowning in chocolate, my son finally asked, “Is this a joke?” Then my daughter walked in and said, “Ugh… another Wonka lesson.”
After those two not-so-nice comments from my children, I still continued — dragging them into Veruca Salt. Because if there’s anything more accurate than a sentencing parable, it’s a child demanding, “I want it now.” I haven’t found anything better.
So when I picked up The 33 Strategies of War, I tried to read it like a normal person:
No parallels to prison.
No analogies to sentencing.
No “Here’s what this teaches defendants.”
I even told my buddy Lawrence, “It’s just a book.”
He laughed.
By Chapter 3, with dozens of highlighted pages and notes copied into my phone, I knew this would become something for our community. Greene isn’t just writing about war — he’s writing about human behavior under pressure. Which means he’s writing about defendants, whether he knows it or not.
Why Greene Applies to Sentencing
A quick update before we dive in:
After the Fall, Chapter 6, will be out next week. It covers a conversation I had with Michael Santos immediately after his release from prison — at a McDonald’s next to his halfway house in the Tenderloin District in San Francisco.
Now, back to Greene.
Tayana and I recently finished our new book, 14 Costly Errors That Lead to a Longer Federal Prison Sentence. Part One covers the four foundations of failure:
- Silence
- Excuses
- Inconsistency
- Delays
Greene writes about these same behaviors. Not in courtrooms — in battles.
But human behavior doesn’t care about context. It repeats itself everywhere.
Let’s break down how Greene’s strategies reveal the same patterns we see in federal sentencing.
Foundation One: Silence — Greene’s Death Ground, Sun Tzu, and the False Comfort of Waiting
Greene writes about commanders forcing their own men onto death ground — terrain where there’s no escape. Sun Tzu wrote:
When warriors know there is no way out, they stop fantasizing and start acting.
Defendants do the opposite.
When the indictment arrives, instead of preparing, they tell themselves:
- “Let’s wait.”
- “My lawyer’s got it.”
- “It’s too early to do anything.”
- “I don’t want to make things worse.”
It wasn’t too early for the government to indict you, for banks to fire you, for the DOJ to issue press releases. Get started dammit!
Case Example: The New York Doctor
He prepared seven minutes for his PSR interview. His silence came across as minimizing. Probation wrote:
“The defendant offered very little information and appeared evasive.”
The judge sentenced him to 54 months, the top of the range.
Silence isn’t strategy.
It’s avoidance.
Sun Tzu’s Lesson
Greene calls this self-directed warfare — confronting illusions before confronting your enemy.
Defendants who delay preparation only confront themselves too late.
That’s where regret starts.
Foundation Two: Excuses — Napoleon, Sherman, and Emotional Self-Destruction
Greene’s recounting of Napoleon’s retreat from Russia is devastating.
Napoleon lied to himself about weather, terrain, morale — everything.
Excuses feel good. They destroy outcomes.
Case Example: The Boston Broker
He spent his PSR interview complaining about the DOJ press release. Probation wrote:
“Downplayed the seriousness of his offense and shifted blame.”
The judge gave him 46 months.
Case Example: The Dallas CPA
He didn’t fight the press release. He acknowledged it, used it as a teaching moment for his kids, volunteered consistently, documented everything, and removed all justifications.
The government wanted two years. He received nine months.
Sherman’s Lesson
Sherman teaches: Stop negotiating the past. Move. Act.
Prosecutors advance their careers while defendants defend their feelings.
Foundation Three: Inconsistency — Pericles, Scipio, and the Collapse of Trust
Greene tells the story of Pericles, who watched Athens collapse not because of an external enemy, but because every faction told a different story.
Sentencing works the same way.
Case Example: The Inconsistent Defendant
He gave different versions of himself to every stakeholder:
- remorse to the judge
- defensiveness to probation
- anger to prosecutors
Not intentional — but damaging.
Case Example: The Seattle Tech Founder
He aligned everything:
- restitution plan
- compliance training
- volunteer work
- release plan
- communication with prosecutors.
He got nine months instead of 18-months in federal prison.
Scipio’s Lesson
Same troops, same terrain — unified strategy wins.
Consistency builds credibility.
Foundation Four: Delay — Genghis Khan, Frederick the Great, Mao, and the Cost of Waiting
Greene uses Genghis Khan to show the power of early movement.
Khan didn’t wait. He moved before enemies organized.
Defendants wait for the “right time.” It never comes.
Case Example: The L.A. Financial Advisor
He wrote his apology a few days before sentencing.
Opened with:
“I take full responsibility, but…”
Too late. He got 37 months.
Case Example: The Defense Attorney
He owned his conduct immediately:
- notified the board
- built a transition plan
- volunteered early
- documented everything
He got 11 months — and a rare self-surrender date.
Frederick & Mao’s Lessons
Frederick hesitated and paid.
Mao pivoted early and survived.
Defendants who pivot early benefit. Those who wait get crushed.
The Real Connection
Under every Greene story is the same truth defendants know:
People make the worst decisions of their lives while trying to avoid discomfort.
Preparation is uncomfortable.
Regret is worse.
What You Can Do Today
Think from the perspective of stakeholders:
- Prosecutors want career advancement.
- Judges respect accountability and structure.
- Probation looks for sincerity, authenticity.
Ask:
- What values am I demonstrating today?
- Have I documented them?
- Are they real or last-minute?
Defendants don’t only get longer sentences because of what they did.
They get longer sentences because of how they respond.
FAQ
How can Robert Greene’s strategies help someone facing federal sentencing?
Greene explains how humans behave under pressure—panic, denial, delay, excuses. These behaviors match what defendants do after indictment.
FAQ
How can Robert Greene’s strategies help someone facing federal sentencing?
Greene explains how humans behave under pressure—panic, denial, delay, excuses. These behaviors match what defendants do after indictment.
What are the four biggest mistakes defendants make?
Silence, excuses, inconsistency, and delay.
Why does silence hurt defendants?
It reads as minimizing or evasive to probation and judges.
Why is consistency important?
All stakeholders read your file. Mixed messaging damages credibility.
How does the PSR affect sentencing?
Simple, the words the probation officers writes will influence how long someone serves in federal prison.
What should defendants do immediately after pleading guilty?
Begin building assets that show why they are different than the government’s version of events.
Resources & Links
Internal Links
External Links
About the Author
Justin Paperny is the founder of White Collar Advice and author of Lessons From Prison and Ethics in Motion. After serving a federal prison sentence in 2008, he dedicated his career to helping defendants prepare for sentencing, navigate prison, and rebuild their lives with integrity and discipline. His work has been featured by CNN, Fox News, The Washington Post, Forbes, and many others.
Call to Action
Join our next Tuesday webinar where Tayana and I walk through these strategies in detail.
Ready to prepare for sentencing the right way? Schedule a call with our team today.
