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 They happen in the cracks of a system—one that’s either outdated… or working exactly as designed.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.