In this episode of The Fine Line Files, Dominique Molina and Tom peel back the layers on one of the most controversial—and misunderstood—tax strategies in modern history: conservation easements.

What started as a well-intentioned policy to protect land and promote environmental stewardship quietly transformed into one of the IRS’s most aggressively targeted tax battlegrounds. Billions of dollars. Explosive valuations. Senate outrage. And an audit spotlight so intense most tax professionals won’t even say the words out loud.

Today, we break the silence.

• What a conservation easement actually is—and why it qualifies as a charitable deduction

• How “highest and best use” valuations turned land preservation into a tax goldmine

• Why syndicated conservation easements became the IRS’s public enemy number one

• The four hallmarks that can land a deal on the listed transaction watchlist

• How a 2.5x valuation multiple became the real tripwire

• The difference between donating your own land and joining a syndicated deal

• Audit risk, valuation risk, and penalty exposure—what’s real and what’s hype

• Why conservation easements aren’t dead… just quieter, tighter, and evolving

Between 2010 and 2017, taxpayers claimed over $26 billion in conservation easement deductions—and the IRS has been trying to claw them back ever since. The result? A legal minefield where one missing attachment or appraisal sentence can detonate an entire deduction.

This episode doesn’t sell the strategy. It doesn’t condemn it either.

Instead, it explains why conservation easements live squarely on the fine line—and why understanding that line matters more than ever for taxpayers and advisors alike.

We go deeper into how tax incentives meant to protect land became a battleground of auditors, appraisers, promoters, and regulators—and how to navigate this space without stepping on a financial landmine.

Because in tax planning, the line between strategy and scheme is thinner than you think.

Stay curious. Stay vigilant. Stay on the right side of the Fine Line.

In this episode of Tax Crime Junkies, Dominique Molina and Tom Gorczynski unravel one of the largest syndicated conservation easement fraud schemes in U.S. history—an operation that generated over $1.3 billion in false tax deductions while hiding behind the language of land preservation.

What began as a seemingly noble effort to conserve rural land in North Carolina evolved into a nationwide tax shelter machine fueled by inflated appraisals, compliant professionals, and promises that sounded too good to be true because they were.

At the center of it all: CPA Jack Fisher, a trusted insider who understood the tax code well enough to exploit it.

And haunting the story to this day: Kate Joy, the investor-relations coordinator who vanished just as the federal indictments landed.

We break down how Fisher and his network:

• Turned conservation easements—a legitimate charitable tax incentive—into a mass-marketed tax shelter

• Used pre-determined appraisal values to guarantee investors a fixed 4:1 deduction ratio

• Structured partnerships to obscure land values and acquisition costs

• Paid CPAs millions in disguised commissions to promote the deals

• Expanded deductions when offerings were oversold instead of disclosing dilution

• Created paperwork that looked perfectly compliant… while hiding fraudulent intent

On paper, everything checked out. In reality, the deduction was the product.

This isn’t just a story about one bad actor.

It’s about:

• How legitimate tax incentives can be weaponized

• The ethical responsibilities of CPAs, EAs, and advisors

• The danger of “clean” paperwork masking fraudulent substance

• Why the IRS and Congress are now aggressively targeting syndicated conservation easements

And it’s a reminder that when a tax strategy requires secrecy, backdating, or “just trust us”… the ending is rarely a happy one.

In Part Two, we’ll cover:

• The federal indictments and sentences

• The IRS crackdown on syndicated conservation easements

• Congressional attempts to reform the law

• The ongoing battle between conservation, compliance, and abuse

And we’ll zoom out to answer the big question: Can conservation easements survive after schemes like this?

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.