The Tax Times

Thursday, May 7, 2026

Taxpayers Need to Consider Documenting Business Purpose After Liberty Global

In a highly anticipated and long awaited decision, on April 21 the U.S. Court of Appeals for the Tenth Circuit ruled in favor of the IRS in Liberty Global Inc. v. U.S. The court held that Liberty Global's disputed transactions lacked economic substance and that the economic substance doctrine did not require a threshold relevancy determination to be applied.

Setting the stage: why Liberty Global matters

For years, the codified economic substance doctrine in section 7701(o) sat atop an already muddled common‑law landscape, with courts disagreeing on when the doctrine is “relevant” and how intrusive it should be in evaluating tax‑motivated planning. Congress tried to clarify, not replace, existing doctrine in 2010, expressly limiting section 7701(o) to “any transaction to which the economic substance doctrine is relevant,” but never defining what “relevant” means. Initially, the IRS imposed internal executive‑level approval requirements before agents could assert economic substance and the strict‑liability penalties under sections 6662(b)(6) and 6662(i), but those approvals were lifted in 2022 following TIGTA criticism that the Service was under‑using the doctrine in large corporate and partnership cases. Since then, exam teams have invoked economic substance with increasing frequency, often against complex corporate restructurings and cross‑border plans that formally comply with Code mechanics but generate eye‑catching tax benefits.

The Liberty Global transaction and holding

Liberty Global’s “Project Soy” was a four‑step cross‑border restructuring designed to exploit a timing mismatch among the GILTI, Subpart F, and section 245A regimes to transform approximately 2.4 billion dollars of gain into a dividends‑received deduction. In the district court, Liberty Global conceded that the first three steps of the plan failed the two‑prong economic substance test—no meaningful non‑tax economic change and no substantial non‑tax purpose—leaving on appeal only whether section 7701(o) was even “relevant” to Project Soy. A divided Tenth Circuit affirmed the District of Colorado, holding that the codified economic substance doctrine applies even when the taxpayer has mechanically followed the literal terms of the Code, so long as the resulting tax benefit is not one Congress can reasonably be thought to have intended. The majority further rejected the argument that common M&A elements or ordinary business steps are categorically immune from economic substance review, emphasizing that section 7701(o)(5)(D) permits courts to analyze an integrated series of steps as a single transaction even when individual pieces resemble routine business moves.

U.S. Circuit Judge Allison Eid dissented, reading section 7701(o)’s “relevant” language as demanding a threshold inquiry before courts can apply the doctrine, and warning that skipping this step invites economic substance into ordinary‑course transactions Congress did not mean to police in this way. Her dissent provides a roadmap for further litigation, including a possible en banc request in the Tenth Circuit or a future certiorari petition that squarely asks the Supreme Court to define “relevant” for purposes of section 7701(o).

How Liberty Global fits with Patel and Perrigo

Recent cases underscore that Liberty Global is part of an emerging split on the scope of the doctrine and the role of the relevancy requirement.

· In Patel v. Commissioner, a reviewed 2025 Tax Court decision involving microcaptive insurance arrangements, the court held that Congress “could hardly have been clearer” that the economic substance doctrine is only relevant to certain transactions. After expressly conducting a relevancy inquiry under section 7701(o), the Tax Court concluded the microcaptive structure lacked both meaningful non‑tax economic change and substantial non‑tax purpose, disallowing the deductions and sustaining 20% and 40% strict‑liability penalties. Patel is now on appeal to the Fifth Circuit, which will have an opportunity to endorse or refine the Tax Court’s articulation of the relevancy requirement.

· In Perrigo Co. v. United States, the Western District of Michigan rejected the government’s attempt to invoke common‑law economic substance and related sham doctrines to disregard an intercompany assignment of contract rights to a controlled Israeli affiliate. The court found the restructuring had genuine business drivers and declined to treat economic substance as a catch‑all anti‑abuse tool where section 482 and other specific provisions already provided a tailored framework. Although Perrigo addressed the uncodified doctrine rather than section 7701(o), it signals judicial skepticism toward using economic substance to override transactions that fit cleanly within detailed statutory and regulatory regimes.

Taken together, Patel and Perrigo stand in tension with the Tenth Circuit’s willingness in Liberty Global to treat “relevance” as essentially satisfied whenever a taxpayer uses Code mechanics to achieve a result courts view as inconsistent with congressional intent. That divergence increases the odds that the appellate courts—and eventually the Supreme Court—will be asked to draw clearer lines around when economic substance can and cannot be deployed.

Different judicial approaches at a glance

Case	Court / Circuit	Doctrine applied	Approach to “relevance” or scope	Outcome for taxpayer
Liberty Global	10th Cir. (appeal from D. Colo.)	Codified §7701(o)	Majority treats doctrine as relevant to mechanical use of Code to obtain unintended benefits; no separate threshold carve‑out for ordinary‑looking steps.	Government win; 2.4B dollar benefit denied.
Patel	Tax Court (appeal to 5th Cir.)	Codified §7701(o)	Explicit relevancy inquiry; emphasizes that doctrine is limited to “certain transactions” and not universal.	Government win; microcaptive deductions disallowed; penalties sustained.
Perrigo	W.D. Mich. (appeal to 6th Cir.)	Common‑law economic substance and sham doctrines	Treats doctrine as inapplicable where detailed rules (e.g., section 482) fit better and transactions show real business substance.	Taxpayer win; intercompany assignment respected; substantial refund allowed.

Implications for planning, exams, and penalties

The Liberty Global majority opinion is likely to embolden the IRS to assert economic substance more aggressively in cases where taxpayers have exploited timing, hybrid entities, or structural asymmetries in the Code to achieve large deductions or deferrals. Tax advisors can expect exam teams to cite Liberty Global when challenging cross‑border restructurings that are technically compliant but difficult to square with a principled reading of congressional intent, especially in the GILTI, Subpart F, section 245A, and related international regimes. Because section 7701(o) carries strict‑liability penalties—40 percent for undisclosed transactions and 20 percent with adequate disclosure—the risk calculus around “mechanical” planning has shifted further in the government’s favor, particularly in the Tenth Circuit and in cases likely to influence national guidance.

At the same time, Perrigo offers a counter‑narrative for taxpayers arguing that economic substance should not be used as a blunt instrument where more precise tools like section 482 already exist and where transactions have clear commercial rationales. Patel demonstrates that courts are capable of conducting a disciplined relevancy analysis and still reaching a government‑favorable result, which could appeal to appellate judges concerned about unchecked judicial anti‑abuse doctrines. If the Fifth and Sixth Circuits embrace Patel’s and Perrigo’s more bounded views, the split with the Tenth Circuit’s Liberty Global framework will become sharper and potentially ripe for Supreme Court review.

Practical takeaways for taxpayers and advisors

From a practical standpoint, Liberty Global reinforces that taxpayers cannot safely rely on formal compliance with Code text alone when the economic outcome appears tax‑driven and disconnected from business realities. To mitigate audit and litigation risk:

· Elevate business purpose: Ensure that every major step in a transaction can be tied to a concrete business objective—operational efficiency, market access, regulatory requirements, financing needs—supported by contemporaneous evidence. Advisors should help clients articulate these rationales in clear, non‑tax‑centric terms.

· Build a cohesive documentary record: Maintain a consistent story across board materials, internal slide decks, tax memos, external opinions, emails, and press releases; inconsistencies or “tax‑only” project names create fertile ground for an economic substance challenge. Contemporaneously document alternative structures considered, why they were rejected, and how the chosen path better addressed the underlying business problem.

· Preserve key transaction artifacts: Keep detailed reorganization plans, financial projections pre‑ and post‑transaction, valuation reports, legal opinions, and operational integration documents readily accessible for a future exam. Identifying a clear business “owner” for each transaction—someone who can credibly explain commercial motivations—is often as important as the written record.

· Rethink penalty posture and disclosures: Given the strict‑liability penalties and the Tenth Circuit’s expansive reading of “relevance,” taxpayers should carefully evaluate whether protective disclosures are warranted for significant tax‑motivated restructurings, especially those involving legislative gaps or timing mismatches. Opinions should analyze not just literal statutory compliance but also how a court might view economic substance in light of Liberty Global, Patel, and Perrigo.

Liberty Global is unlikely to be the last word on economic substance, but it meaningfully re‑weights the balance between taxpayer reliance on statute text and judicial anti‑abuse authority.

Need Advice on Tax Restructuring?

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Sources:

1. https://www.pwc.com/us/en/services/tax/library/us-court-of-appeals-rules-against-liberty-global.html

2. https://www.ntu.org/foundation/detail/tenth-circuit-liberty-global-decision-unfortunately-supports-broad-interpretation-of-economic-substance-doctrine

3. https://www.davispolk.com/insights/client-update/divided-10th-circuit-affirms-district-court-economic-substance-doctrine

4. https://www.cov.com/en/news-and-insights/insights/2026/04/tenth-circuit-grants-us-win-on-economic-substance-in-closely-watched-liberty-global-tax-case

5. https://www.thetaxadviser.com/issues/2026/feb/penalties-under-codified-economic-substance-doctrine-upheld/

6. https://www.ca10.uscourts.gov/sites/ca10/files/opinions/010111286948.pdf

7. https://www.law360.com/articles/2468310/liberty-global-loses-2-4b-tax-substance-fight-in-10th-circ

8. https://www.currentfederaltaxdevelopments.com/blog/2025/11/12/examining-penalties-in-microcaptive-transactions-patel-v-commissioner

9. https://www.captive.com/news/tax-court-addresses-economic-substance-and-disclosure-penalties-in-micro-captive-case

10. https://insightplus.bakermckenzie.com/bm/dispute-resolution/united-states-district-court-upholds-economic-substance-of-intercompany-transactions-in-perrigo

11. https://www.millerchevalier.com/publication/perrigo-opinion-upholds-economic-substance-intercompany-assignment-contract-rights

12. https://taxnews.ey.com/news/2026-0397-district-court-judge-approves-final-judgment-in-case-on-economic-substance-doctrine

13. https://www.hklaw.com/en/insights/publications/2024/05/beware-liberty-global-appeal-puts-basic-tax-planning-in-jeopardy

14. https://www.currentfederaltaxdevelopments.com/blog/2026/4/21/the-tenth-circuit-codifies-the-reach-of-the-economic-substance-doctrine-over-mechanical-statutory-compliance

15. https://captivereview.com/news/tax-court-upholds-penalties-in-patel-micro-captive-case/

Borrowed From the IRS: How Payroll Tax Evasion Turns Small Shortcuts Into Big Trouble

Payroll tax evasion is quietly becoming one of the riskiest “shortcuts” a business can take, and recent cases show that the government is responding with longer prison sentences and bigger crackdowns, especially in construction and other labor‑intensive industries.

What Payroll Taxes Are – And Why They Matter

When you get a paycheck, your employer withholds money for income tax, Social Security, and Medicare, and then sends those funds to the IRS on your behalf. The employer also pays its own share of Social Security and Medicare taxes on top of what is taken from employees’ checks.

These withheld amounts are called “trust fund” taxes because the employer is holding them in trust for the government and for workers’ future benefits. They are a major source of funding for Social Security, Medicare, and a large chunk of overall federal income tax collections.

How Payroll Tax Evasion Works

Payroll tax evasion happens when a business withholds taxes from paychecks but never sends them in, or simply never withholds what it should in the first place. Sometimes owners do this to prop up a struggling business for “just a few months,” and other times they do it to fund a more lavish lifestyle.

Common schemes include:

· Paying workers in cash “off the books”

· Treating clear employees as “independent contractors” to dodge withholding

· Running wages through shell companies or check‑cashing services

· Withholding taxes from paychecks but using the money as a personal or business slush fund

In construction, authorities say they are seeing large networks of shell companies and fraudulent documents used to avoid payroll taxes and workers’ compensation premiums, costing governments hundreds of millions of dollars a year.

Real People, Real Prison Time

Recent prosecutions show what can happen when payroll taxes are treated like extra cash instead of a legal obligation. One Dallas staffing‑company owner failed to send more than $3 million of withheld payroll taxes to the IRS and instead used the money for international travel, luxury goods, and a $10,000‑a‑month home. After a jury trial, she was sentenced to more than eight years in prison and ordered to pay hundreds of thousands of dollars in restitution.

In another case, a former Virginia business owner withheld employment taxes over many quarters but didn’t file returns or pay the IRS, causing about $3.1 million in tax loss and earning a sentence of more than six years in prison. The Justice Department emphasizes that timely payment of these taxes is “critical to the functioning of the U.S. government” and that they will “fully pursue” these offenses to protect tax dollars.

These are not isolated stories; commentators and watchdogs have noted that the number and size of payroll tax violations are increasing, and that traditional civil penalties alone are not enough to stop the trend.

Why Enforcement Is Ramping Up

Several developments are driving tougher enforcement around payroll taxes:

· Focus on high‑risk areas: IRS Criminal Investigation and the Justice Department’s Tax Division list employment tax fraud as a major priority, because every unpaid dollar multiplies quickly through interest, penalties, and harm to federal programs.

· Construction crackdowns: FinCEN and IRS investigators recently issued a joint notice warning of a “concerning increase” in payroll tax evasion and workers’ comp fraud in residential and commercial construction, especially involving shell companies and check‑cashing operations.

· Better data tools: Authorities are increasingly using bank‑report data and analytics to spot suspicious patterns, such as large cash withdrawals and complex flows through multiple business accounts that suggest hidden payrolls.

Regulators have even highlighted how Bank Secrecy Act reporting by banks can help expose payroll tax and insurance fraud schemes, making it harder to hide these activities in the shadows.

What Business Owners Should Take Away

For honest business owners, the message is simple: payroll taxes are never optional, even in a cash crunch. The government treats them as money that belongs to employees and the public, not to the company, which is why violations often trigger both steep civil penalties and criminal charges.

If a business falls behind, the safest move is to get professional help quickly, work with the IRS, and avoid making matters worse by trying to “borrow” from payroll tax funds. Recent cases show that once prosecutors believe an owner knowingly crossed the line and ignored warnings, prison time and large restitution orders are very much on the table.

If you were reading this as a potential client or business owner, would you find it more helpful to see a short checklist of “do’s and don’ts” to stay out of payroll‑tax trouble?

Have Payroll Tax Problems?