If you’ve been following the Brockman–Smith saga, you already know this: the biggest tax crimes don’t just happen in the shadows. They happen in the cracks of a system—one that’s either outdated… or working exactly as designed.

In this episode, Dominique sits down again with Jens Heycke, author of Death, Taxes, and Turduckens, and Corey Smith, longtime DOJ tax prosecutor, to zoom out from the scandal and talk about the bigger issue: why schemes like this are possible—and what it would actually take to prevent the next one.

This is a reform episode, but it’s not partisan. It’s about incentives, enforcement, complexity, and the uncomfortable math of who can afford to fight the IRS—and who can’t.

• A clear explanation of the tax gap—what it is and what it includes (underreported income, offshore concealment, false deductions, fake entities)

• Why Jens says the U.S. tax gap is ~$447B/year for personal income taxes alone—and over $600B when corporate tax is included

• The “other gap” nobody talks about: legal avoidance (preferential rates and rules like carried interest) and why it’s so hard to define or measure

• Jens’s estimate that “legal loopholes” could be 2–3x the tax gap (depending on definitions)—potentially trillions

• The shocking double-cost problem:

  • ~$447B lost to underpayment/evasion

  • ~another ~$447B spent on compliance (recordkeeping, filing, paid help)

  • Together: roughly $1 trillion in economic drag

• Corey’s take on why simplification and enforcement matter—but offshore secrecy is still the biggest practical obstacle

• The reform Corey wanted for decades: treat fraudulent offshore entities differently than legitimate privacy-protected accounts

• Why reforms often stall: they aren’t “sexy,” and politicians don’t see a win in championing tax enforcement

• Jens’s argument that tax compliance is regressive: smaller businesses spend far more (as a % of income) on compliance than billionaires

• How complexity fuels regressiveness: more code = more advantage for people who can afford experts

• A fascinating comparison: Estonia’s flat tax system and tiny tax code—versus the U.S. “industry” built around navigating complexity

• Jens’s behavioral economics idea: a Top Taxpayer List—turning ego and competition into voluntary compliance

• A hard truth about deterrence: in 2023, only 363 people were convicted of tax fraud—making prosecution feel rare and non-threatening

• Corey’s view on what deters best: high-profile cases against the biggest players (because the public pays attention)

• How to get the public to care: big cases, big headlines, then use that moment to educate

Complexity is a feature, not a bug… for the people who can afford it. The more complicated the code, the more it rewards scale.

Jens Heycke — Author of Death, Taxes, and Turduckens, focused on the incentives and failures that make billion-dollar evasion possible. Corey Smith — Former DOJ tax prosecutor, bringing decades of frontline experience on what works (and what doesn’t) in enforcement.

In our last episode, we peeled back the layers of the “Turducken”—the offshore nesting-doll structure allegedly used to hide billions. Today, we go inside the investigation with the people who lived it: Jens Heycke, author of Death, Taxes, and Turduckens, and Corey Smith, the longtime DOJ prosecutor who helped build the case.

This conversation is part true-crime thriller, part investigative masterclass: encrypted messages hidden inside photos, false-bottom briefcases, a psychiatrist taking the Fifth in court, and an offshore infrastructure so layered that even the IRS nearly walked away from chasing the assets.

If you liked The Big Short or Catch Me If You Can, this is that… but in the tax world.

• How Jens first got pulled into the Brockman story—and why it had “bad blood” energy from the beginning

• What the “Turducken” actually is (and why it’s the perfect metaphor for offshore schemes)

• A simple explanation of the layered structure: trust → offshore company → offshore company → foreign bank account

• How prosecutors actually start tracing cases like this (domestic accounts outward + foreign ownership back inward)

• What made the Brockman structure different: the income allegedly never touched U.S. hands to begin with

• Why nominee controllers are both the “solution” and the Achilles’ heel of offshore concealment

• The critical Bermuda raid that seized a key computer—and why it triggered Brockman’s downfall

• Why Jens says it’s “horrifying” the IRS nearly gave up chasing the assets after Brockman died

• The “Tweel ruling” separation between civil and criminal IRS enforcement—and how it can leave money unrecovered

• What this case cost to prosecute (Corey’s estimate) and why the return on investment still makes it worth it

• The bombshell meeting where the Attorney General made the call not to indict Robert Smith—and how Corey handled it

• The “wish list” of 14 demands Robert Smith agreed to in exchange for the non-prosecution agreement

• Corey’s candid take on the psychology of white-collar criminals: insecurity + arrogance wrapped together

• Why billionaires can “buy time” with endless litigation, and how that intimidates agencies into backing down

• Jens’s take on enforcement “economies of scale”—and why tax defense is easier the richer you are

• A teaser for the next episode: reform ideas to fix the system that makes Turduckens possible

Jens Heycke — Author of Death, Taxes, and Turduckens, investigative writer tracing offshore secrecy from the Caribbean to the courtroom. get your copy here

Corey Smith — Former DOJ prosecutor with 33+ years experience leading major tax fraud prosecutions, including the Brockman case.

In this episode of Tax Crime Junkies, hosts Dominique Molina and Tom Gorczynski unravel one of the most astonishing tax crime stories in U.S. history — the intertwined rise and fall of Robert Smith, billionaire private-equity titan and philanthropist, and Robert Brockman, the secretive software mogul behind the largest individual tax-evasion case ever charged.

The story opens with a moment of national celebration: Robert Smith pledging to pay off the entire student debt of Morehouse College’s Class of 2019. But behind that generosity lies a labyrinth of offshore trusts, nominee settlors, shell companies, and concealed bank accounts — what author Jens Heycke famously calls a “Turducken” of tax evasion.

Dom and Tom trace Smith’s ascent from Bell Labs prodigy to Goldman Sachs banker to founder of Vista Equity Partners — and his fateful partnership with Brockman, who taught him a sophisticated offshore blueprint designed to hide income from the IRS while maintaining total control.

As the scheme grows, so do the cracks:

• a high-stakes divorce demanding full financial disclosure

• a Swiss bank turning over account data to U.S. authorities

• a massive charitable pledge quietly withdrawn

• trustees smashing hard drives with hammers while racing to the airport

What follows is a dramatic collision between ambition, secrecy, and enforcement — culminating in a non-prosecution deal for Smith and a 39-count indictment against Brockman, whose case would never reach trial.

This episode isn’t just about two men. It’s about beneficial ownership, where legal tax planning ends and criminal evasion begins, and why even the most complex schemes collapse under real-world pressure.

• The Morehouse College moment that shocked the nation

• Who Robert Smith really is — visionary, philanthropist, tax evader… or all three

• Robert Brockman’s offshore empire and the A. Eugene Brockman Charitable Trust

• How the “Turducken” offshore structure actually works

• Carried interest: legal tax planning vs. criminal concealment

• Why foreign trusts use nominee settlors — often elderly relatives

• Beneficial ownership and why paperwork doesn’t control tax outcomes

• The spending sprees that gave the scheme away

• Divorce as the ultimate tax-crime truth serum

• The withdrawn charitable donation that blew Brockman’s cover

• Protective refund claims and the IRS “checkmate” moment

• Evidence destruction, hammer-smashed hard drives, and panic

• Why Robert Smith avoided indictment — and Brockman didn’t

• The dementia defense, competency hearings, and ultimate collapse

• Key lessons for taxpayers, CPAs, and advisors

• Death, Taxes, and Turduckens by Jens Heycke - get your copy here

• DOJ Offshore Voluntary Disclosure Program (OVDP)

• FBAR penalties and foreign account reporting

• Preqin, private-equity performance database

Next week on Tax Crime Junkies, we go inside the case.

We’re joined by:

• Jens Heycke, author of Death, Taxes, and Turduckens, and

• Corey Smith, the DOJ senior prosecutor who led the Brockman prosecution

You’ll hear firsthand how the case was built, why Robert Smith was spared indictment, and what this story reveals about the strengths — and failures — of the U.S. tax system.

What if one of the largest, wealthiest sectors in America never had to file a tax return?

In this episode of The Fine Line Files, Dominique Molina takes listeners inside one of the oldest—and most controversial—features of the U.S. tax system: church tax exemption.

From its origins in the Roman Empire to a bombshell 2025 IRS decision allowing churches to endorse political candidates from the pulpit, this episode unpacks how religious organizations became some of the most protected—and least scrutinized—entities in the tax code.

This is not an attack on faith. It’s an investigation into power, money, history, and the rules that govern them.

• Why churches have been tax-exempt for nearly 1,700 years

• How federal income tax exemption for churches became law in 1894

• The unique tax privileges churches enjoy today—including automatic 501(c)(3) status and no Form 990 filings

• The parsonage exemption and why clergy housing is treated differently than any other nonprofit leader

• The 2025 IRS pivot that now allows churches to endorse political candidates during religious services

• A dramatic case study: Scientology vs. the IRS and the 25-year legal war over tax-exempt status

• Why taxing churches would not fix the federal budget (and what the numbers really say)

• The strongest arguments for and against church tax exemption

• Where the real “fine line” lies between religious liberty and government subsidy

Is tax-free status a constitutional shield protecting religious freedom… or a mask that sometimes hides behavior we’d never tolerate in any other sector?

As always, Dominique invites listeners to question assumptions, follow the money, and decide for themselves where the line should be drawn.

In this episode, we dive into two of the most feared audits in American life: the IRS audit… and the Scientology audit. One asks for receipts. The other asks for your deepest spiritual secrets. And neither one thinks “I don’t remember” is an acceptable answer.

Join Dominique Molina and Tom Gorczynski as they unravel the decades-long war between the Church of Scientology and the Internal Revenue Service — a conflict that involved covert operations, infiltrations, forged IDs, wiretaps, thousands of lawsuits, and one of the strangest reversals in IRS history.

• How Scientology’s version of “auditing” works — and why it can cost up to $800 an hour

• The IRS’s early suspicion that Scientology was “a profit-making scheme for Hubbard’s personal enrichment”

• How the 1967 revocation of Scientology’s tax-exempt status launched a 26-year legal and covert battle

• Scientology’s spy operations inside federal agencies — including the IRS, DOJ, DEA, and more

• The largest FBI raid in history targeting Scientology offices

• How 11 high-ranking Scientologists ended up convicted and sent to prison

• Scientology’s strategy of overwhelming the IRS with 200 lawsuits from the church and 2,300 from individual members

• The mysterious 1991 meeting that allegedly changed everything

• Why the IRS granted Scientology tax-exempt status in 1993—despite repeated court rulings against them

• What the leaked agreement revealed (hint: Scientology paid $12.5 million instead of more than $1 billion in back taxes)

• The constitutional questions that continue to haunt this decision

The Scientology–IRS saga isn’t just a story about tax exemption. It’s a story about power, pressure, and the limits of government oversight. It reveals how far a determined organization can go to bend the system—and how even the most powerful tax agency in the world can be pushed to its breaking point.

• John Oliver on IRS church exemptions https://youtu.be/7y1xJAVZxXg?t=550

• John Oliver creating his own church https://youtu.be/7y1xJAVZxXg?t=895

When religion meets revenue, the waters get murky. The paper trail always tells the real story.

How Scammers Borrow Credibility — and How to Spot It

In this episode of The Fine Line Files, Dominique Molina unpacks the unsettling case of Sherry Peel Jackson — a former IRS agent, CPA, and Certified Fraud Examiner whose professional authority became the perfect disguise for one of the most persistent financial fantasies in America: the tax defier movement.

But this isn’t just a story about tax law or conspiracy theories. It’s a story about credibility — how it’s earned, how it’s manipulated, and how easily it can be misused.

Fraudsters don’t succeed because their schemes are brilliant. They succeed because their messengers look legitimate.

Through Sherry’s journey from IRS insider to anti-tax crusader, we explore:

• Why scammers recruit people with titles, credentials, and insider backgrounds

• How movements use “beards” to make false claims feel true

• Why intelligent, well-trained professionals can still fall for misinformation

• The difference between real expertise and performative authority

• Simple tests to tell whether a testimonial is trustworthy—or a trap

In a world overflowing with polished social media experts, paid reviews, “former government insiders,” and influencers selling certainty, this episode offers a practical guide to spotting the difference between a trusted voice… and a well-positioned prop.

Because facts don’t need a beard. Only scams do.

• How do you know who to trust online?

• How do scams use credible people to lure victims?

• Why do smart professionals sometimes fall for bad information?

• What’s the difference between questioning the system and rejecting reality?

What happens when an IRS insider trades audits for anti-government conspiracies? In this week’s episode, we dive headfirst into the tangled world of the Tax Defier Movement a universe of pseudolegal theories, fringe seminars, cruise-ship conferences, and people who genuinely believe the income tax is optional.

Our case study? Sherry Peel Jackson, a former IRS agent, CPA, and Certified Fraud Examiner who went from enforcing the tax law… to denying it applies at all. After discovering a full-page ad claiming that “income taxes is a fraud,” Jackson fell down a rabbit hole of books, seminars, and misinformation that would eventually lead to a four-year federal prison sentence.

Join Dominique and Tom as they trace Jackson’s journey from respected IRS employee to one of the most notable faces of the modern anti-tax movement. Along the way, you’ll hear:

How an ad in USA Today helped fuel a nationwide surge in tax-defier ideology The rise (and spectacular fall) of the Global Prosperity and PQI schemes Why cruise ships are apparently the unofficial headquarters of tax fraud The most common (and most debunked) myths tax defiers swear by Section 861, the 16th Amendment, 5th Amendment claims, and more How the IRS and DOJ have responded to the growing wave of “tax truthers” Why rhetorical attacks on the legitimacy of the tax system not lost revenue pose the real threat

This episode untangles the conspiratorial logic behind the Tax Defier Movement and shows why these arguments fail in court every. single. time. Spoiler: judges don’t accept “I am a sovereign citizen of my own bedroom” as a legal defense.

By the end, you'll understand how an intelligent, credentialed professional can get swept into a movement built on flimsy interpretations and wishful thinking and why the IRS will never, ever buy the claim that taxes are voluntary.

If you’ve ever wondered how misinformation spreads, who profits from it, and why so many smart people fall for bad tax advice… this episode is your case study.

What happens when a man who built a $200 million business on lies tries to warn you about someone else’s fraud?

In this Tax Crime Junkies Fine Line Files special edition, Dominique sits down with Barry Minkow—the teenage mastermind behind ZZZZ Best, the ex-con-turned-pastor-turned-SEC informant—for a one-of-a-kind interview.

But this isn’t the redemption arc you might expect.

Instead, Dom gets a front-row seat to monologue filled with red flags, Reg D horror stories, and just enough self-awareness to leave you wondering: Is he helping protect people—or just starring in his next act?

In this episode, you’ll hear:

🔹 Why Reg D investment deals are a playground for fraud 🔹 How repeat offenders can sound convincing—even while making confessions 🔹 What Barry says about his own history, and the victims he now advocates for 🔹 The subtle, dangerous charisma of a career con man

And the chilling takeaway from Barry himself:

“Perpetrators of financial fraud can’t guard the front door. And only a crook like me would know that.”

🎧 This episode is a warning, a case study, and a reminder: even a man who lies for a living can sometimes tell the truth. But that doesn’t mean you should trust him.

Call to Action: Have you seen a shady Reg D deal pitched to one of your clients? Know a repeat fraudster who keeps popping up in the industry? We want to hear your story. Leave us a voicemail on our hotline or DM us @TaxCrimeJunkies.

Subscribe, share, and remember: Stay curious. Stay vigilant. And stay on the right side of The Fine Line.