Chapter 26: The Line Crossed
Day 92, and Louis brought me the biggest case of the quarter.
"Whitmore Industries. Family-owned manufacturing company, hundred-year history, selling to a tech conglomerate for three hundred forty million."
He set a stack of folders on my desk—easily three feet tall.
"The patriarch wants a clean exit into retirement. Hired us to make sure the deal closes without complications. Harvey's team is handling the acquirer side. We're representing the sellers."
I looked at the mountain of documents.
"What's my role?"
"Comprehensive due diligence. Five years of financials, corporate structure, subsidiary operations. Find anything that might give the acquirer cold feet or tank the deal."
[WIN RATE CALCULATOR: INITIAL ASSESSMENT]
[SUCCESSFUL DEAL PROBABILITY: 72% (±16%)]
[STANDARD COMPLEXITY: MOTIVATED PARTIES, CLEAR TERMS]
[RISK FACTORS: UNKNOWN LIABILITIES IN FINANCIAL HISTORY]
"Timeline?"
"Three weeks until signing. Start with the most recent financials and work backward."
Louis left, and I began the methodical process of document review.
This is what I'm good at. Finding patterns others miss. Seeing problems before they become disasters.
Day 93, 2:17 AM, and I was deep in subsidiary financial records.
The main Whitmore Industries financials were clean—consistent revenue, manageable debt, reasonable profit margins. But they had seven subsidiary companies acquired over the years, and those were messier.
I was reviewing expense reports for Whitmore Manufacturing Ohio—a small subsidiary acquired in 1987—when the System flagged an anomaly.
[BLACKMAIL ARCHIVE: PATTERN DETECTED]
[EXPENSE REPORTING: IRREGULAR PATTERNS]
[CROSS-REFERENCING: 400+ TRANSACTIONS]
[ANOMALY IDENTIFIED: SYSTEMATIC EXPENSE INFLATION]
I pulled up the detailed transaction records.
Someone had been inflating expense reports. Not dramatically—$45,000 to $80,000 per quarter, buried in legitimate business expenses, shuffled through subsidiary transfers that made the money nearly impossible to trace.
Three years of activity. Approximately $850,000 total.
I dug deeper, following the money trail through corporate accounts, personal reimbursements, credit card charges.
The pattern emerged clearly.
Marcus Whitmore. The patriarch's son. VP of Operations.
Embezzlement. Sophisticated, sustained, and completely missed by the auditors.
I sat back in my chair, staring at the numbers on my screen.
[ARGUMENT CRUSHER: CONSEQUENCE ANALYSIS]
[IF REVEALED: DEAL COLLAPSES]
[ACQUIRER WALKS DUE TO FINANCIAL INTEGRITY CONCERNS]
[FAMILY REPUTATION DESTROYED]
[FIRM LOSES $8M IN FEES]
[CRIMINAL CHARGES LIKELY]
What do I do with this?
The embezzlement had stopped four months ago—Marcus must have gotten nervous, sensing increased scrutiny as the sale approached.
The money was gone. Revealing it now wouldn't recover it. It would just destroy the deal, humiliate the family, and potentially send Marcus to prison.
But it's fraud. Material information that the acquirer deserves to know.
I spent three hours running scenarios.
[SYSTEM ALERT: CRITICAL CHOICE POINT]
[OPTION A: REPORT TO LOUIS IMMEDIATELY]
[ETHICAL: CORRECT]
[OUTCOME: DEAL COLLAPSES, CHAOS ENSUES, FIRM LOSES REVENUE]
[OPTION B: REPORT TO JESSICA DIRECTLY]
[ETHICAL: BYPASSING CHAIN OF COMMAND BUT TRANSPARENT]
[OUTCOME: SAME AS OPTION A]
[OPTION C: ARCHIVE PRIVATELY, EXCLUDE FROM REPORT]
[ETHICAL: QUESTIONABLE TO SEVERELY PROBLEMATIC]
[OUTCOME: DEAL CLOSES, PROBLEM BECOMES LEVERAGE, FAMILY OWES YOU]
I sat with that decision as the sun came up over Manhattan.
The embezzlement isn't ongoing. It's not an active threat to the company's operations. Revealing it serves no purpose except to satisfy abstract ethical requirements.
But keeping it secret is withholding material information. That's a line I've never crossed.
At 7:30 AM, I made my choice.
I created a new entry in my Blackmail Archive—every transaction, every pattern, every piece of evidence meticulously documented and encrypted.
Then I excluded it from my due diligence report.
[BLACKMAIL ARCHIVE: NEW ENTRY CREATED]
[MARCUS WHITMORE - EMBEZZLEMENT]
[AMOUNT: $850,000 OVER 36 MONTHS]
[STATUS: INACTIVE (CEASED 4 MONTHS AGO)]
[EVIDENCE: COMPLETE TRANSACTION PATTERN ANALYSIS]
[CLASSIFICATION: LEVERAGE - FUTURE USE]
[ETHICAL STATUS: WITHHELD MATERIAL INFORMATION]
The System stored it without judgment. But I felt the weight of it.
This is different from everything else I've done. This isn't strategic positioning or calculated networking. This is deliberately hiding fraud.
Day 94, I submitted my due diligence report to Louis.
Comprehensive. Thorough. Clean.
Environmental liabilities: clear. IP transfer issues: clear. Tax compliance: clear. Financial irregularities: none reported.
Louis reviewed it in his office while I waited.
"Perfect work, Scott. Not a single red flag."
"The company's in good shape."
"This is why I trust you with the important cases. Thorough, reliable, excellent analysis."
I nodded, keeping my expression neutral.
He trusts me. And I just betrayed that trust by withholding information.
I left his office and went back to my desk, the weight of what I'd done settling over me like a physical thing.
That evening, alone in my apartment, I sat on my couch with a beer I wasn't drinking, staring at nothing.
The System hummed quietly with its new secret.
First time I've crossed a clear ethical line. Not for survival. Not for defense. For future advantage.
What does that make me?
My phone buzzed.
Donna: Dinner tomorrow?
I stared at the message for a long time.
The person she's dating just became someone slightly different. Someone who withholds fraud for leverage. Someone who calculates morality instead of following it.
I typed back: Yes. 7 PM?
Perfect. I'll pick the place.
I set down my phone and finished my beer.
The System offered no guidance, no probability calculations, no strategic recommendations.
Some choices existed outside its framework.
I'd crossed a line. Deliberately. With full awareness of what I was doing.
Can't uncross it now.
All I could do was decide what to do with the leverage I'd created.
And hope that when the moment came, I'd choose something better than the worst version of myself.
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