The Tax Court’s decision in
Waimana Enterprises, Inc. v. Commissioner
(consolidated with
Albert S.N. Hee and
Wendy R. Hee v. Commissioner, T.C. Memo. 2026‑53) is a case study in what
happens when a closely held C corporation is run as a personal checkbook and
the IRS decides it is done giving the benefit of the doubt.
For owners, officers, and
advisors, the opinion is a roadmap of what the government looks for when
reclassifying corporate spending as constructive dividends and when pushing a
case over the line into civil fraud under section 6663.
The Story: A Corporate Group Used As a Personal
Piggy Bank
Albert S.N. Hee formed
Waimana Enterprises, Inc. in 1988 as a holding company for several subsidiaries
including Sandwich Isles Communications, Clearcom, and a captive insurer,
Ho‘opa‘a Insurance Co. He was the sole shareholder and president of Waimana and
also ran each subsidiary.
Instead of separating
business and personal spending, Mr. Hee routinely used his personal credit
cards for a wide range of charges, had the corporations reimburse him, and then
deducted those charges as business expenses through the operating subsidiaries
and Waimana. Trips taken by other employees went through a formal travel-review
process; trips by Mr. Hee and his family were exempt from that process
altogether.
An IRS examination for
2003–2012 led to a criminal referral. Mr. Hee was convicted in federal court of
corruptly impeding the IRS and filing false returns for 2007–2012, receiving a
46‑month prison sentence and restitution obligations. After that conviction,
the Service asserted large deficiencies and section 6663 civil fraud penalties
against both the individual and the corporation for a broad range of disallowed
deductions and recharacterized payments.
What the Court Disallowed: Personal Life Run
Through the Company
The Tax Court walked
systematically through categories of spending and explained why each failed as
a business deduction and became constructive dividends to Mr. Hee.
Health, education, and family “employment”
·
Massage therapy as “business
expense.”
Waimana paid between $6,000 and $10,000 per year for twice‑weekly, two‑hour
massages for Mr. Hee, which he said were cheaper than replacing him and were
recommended by a chiropractor. The court treated these as inherently personal
health costs, not deductible under section 162, and reclassified them as
constructive dividends.
·
MIT tuition for a child.
The company paid $33,523 to MIT for a daughter’s tuition, room, and board and
booked it as “educational” and “travel” expense. Because her architecture
studies were unrelated to Waimana’s telecommunications business and there was
no broad educational assistance program, the court held this was purely
personal and a constructive dividend.
·
Salaries and benefits to
children and spouse.
Waimana paid substantial salaries and retirement benefits to Hee’s children and
his wife, despite the children being full‑time students on the mainland and the
lack of credible evidence of actual services. The court applied heightened
scrutiny to related‑party compensation, found no bona fide employment
relationship, and treated those payments as benefits to the shareholder under
the assignment‑of‑income doctrine. Similar reasoning applied to the wife’s
purported compensation where evidence showed she was largely a stay‑at‑home
parent.
Travel, entertainment, and lifestyle spending
The opinion is practically a
catalog of how not to handle section
274(d) substantiation.
·
Children’s airfare and
family trips.
The court disallowed children’s airline tickets between college and Hawaii for
lack of any documented business purpose and treated them as constructive
dividends. A 2008 family “business” trip to France and Switzerland, a family
trip to the 2009 presidential inauguration, a Tahiti vacation, a Walt Disney
World trip, and a Hawaii resort “shareholder meeting” all failed either section
162 business‑purpose standards or the strict recordkeeping rules of section
274(d).
·
Clothing, meals, and retail
purchases.
A $1,246 sport coat purchased at Saks for a dinner with Raytheon executives was
nondeductible because it was suitable for general wear, flunking the three‑part
test for clothing expenses. Various charges at Costco, Target, Nordstrom,
meals, and ATM withdrawals labeled as “office expenses” were also reclassified
as constructive dividends due to missing substantiation and obvious personal
character.
The Santa Clara “corporate residence”
Waimana bought a
five‑bedroom house in Santa Clara, California, near Santa Clara University,
supposedly to facilitate visits to a biotech investment near Menlo Park. Two of
the Hee children attended Santa Clara, lived there rent‑free, rented other
rooms to classmates, and kept the rent; Waimana reported no rental income.Him
The court accepted the IRS
expert’s fair market rental value analysis and held that Waimana had no
ordinary and necessary business reason to own the property. The fair rental
value of the lodging provided to the children became constructive dividends to the
parents, totaling more than $192,000 over the years at issue.
“Loans to Shareholder” That Were Really Dividends
Perhaps the most important
structural issue for closely held corporations in the opinion is the treatment
of over $1.1 million booked as “Loans to Shareholders.”
The court applied the
familiar multi‑factor debt‑vs‑equity analysis (including the Welch factors) and focused on objective
indicators:
·
No promissory notes or written loan agreements for years of
advances.
·
No fixed repayment schedule and no collateral.
·
No regular interest accruals; interest was only imputed late in
the game after the CPA firm raised questions during the audit.
·
Questionable ability to repay at the time of the advances.
Although Mr. Hee eventually
made two large “repayments,” one of them was funded using a $1 million dividend
that flowed from the captive insurer up to Waimana and then to him,
undercutting the notion of genuine debt reduction.
By contrast, the same
corporate group had papered and secured a real loan to a non‑shareholder
employee with a note and formal terms, demonstrating that the company knew how
to structure a bona fide loan when it wanted to.
Given those facts, the court
found that the advances booked as shareholder loans were in substance
distributions, taxable as constructive dividends to the extent of earnings and
profits.
Why This Became a Fraud Case, Not Just a Big
Audit Adjustment
The opinion is also
significant for its expansive fraud analysis. To sustain section 6663 penalties
and invoke the fraud exception to the statute of limitations under section
6501(c)(1), the IRS had to show by clear and convincing evidence both an underpayment
and an intent to evade tax.
The court found multiple
“badges of fraud,” including:
·
Consistent, substantial understatement of income exceeding $2
million across 2004–2012.
·
Inadequate records and systematic bypassing of internal travel and
expense controls for the shareholder and his family.
·
Implausible explanations for the business purpose of trips and the
Santa Clara residence.
·
Supplying incomplete and misleading information to tax preparers,
including mislabeling a massage therapist as a consultant and failing to
disclose family salaries and rental activity.
·
Lack of credibility in trial testimony and collateral estoppel
from the prior criminal conviction for filing false returns.
Because a corporation acts
through its officers, the court attributed Mr. Hee’s fraudulent intent to
Waimana and upheld civil fraud penalties against both the individual and
corporate petitioners. The fraud finding also kept the assessment period open
indefinitely for all years at issue, neutralizing what would otherwise have
been powerful statute‑of‑limitations defenses.
Practical Takeaways for Closely Held Corporations
and Their Advisors
For business owners and tax
professionals, Waimana Enterprises
provides a concrete checklist of what to do—and what to avoid.
·
Draw and respect a bright
line between corporate and personal spending.
Running family lifestyle costs through the company is not just an “aggressive”
tax strategy; with enough volume and concealment, it can support a fraud
finding and open closed years indefinitely.
·
Formalize shareholder loans
from day one.
Genuine loans should be documented with signed notes, stated interest at market
rates, fixed maturity, and enforcement mechanisms, and they should be serviced
with real payments that do not themselves come from round‑trip dividends.
·
Treat family compensation
like any other payroll.
For relatives, especially those away at school, maintain job descriptions, time
records, and evidence of actual services, and pay reasonable amounts
commensurate with work actually performed.
·
Follow section 274(d) to the
letter.
Travel, meals, entertainment, and mixed‑purpose trips demand contemporaneous
documentation of amount, time, place, and business purpose. Without that, the
Cohan rule does not rescue the deduction, and the IRS can reclassify the
spending as constructive dividends.
·
Give your preparers the full
story—or do not expect reliance to help.
Good‑faith reliance on a tax adviser collapses if the taxpayer filters or
mislabels information. Mischaracterizing personal expenses as consulting or
office costs is precisely the kind of conduct courts view as evidence of
intentional fraud, not mere negligence.
Have a Criminal Tax Problem?
Contact the Tax Lawyers at
Marini & Associates, P.A.
for a FREE Tax Consultation contact us at:
or Toll Free at 888-8TaxAid (888) 882-9243
Sources:

1.
https://www.currentfederaltaxdevelopments.com/blog/2026/6/23/constructive-dividends-corporate-formalities-and-the-civil-fraud-penalty-comprehensive-analysis-of-hee-v-commissioner
2.
https://www.currentfederaltaxdevelopments.com/blog/2026/6/23/constructive-dividends-corporate-formalities-and-the-civil-fraud-penalty-comprehensive-analysis-of-hee-v-commissioner
3.
https://static1.squarespace.com/static/54a14f8ee4b0bc51a1228894/t/6a4143b5a631a0287c4b6bb5/1782662070032/2026-06-29+Current+Federal+Tax+Developments.pdf
4.
http://oaoa.hawaii.gov/jud/opinions/sct/2006/26519mop.htm
5.
https://kpmg.com/kpmg-us/content/dam/kpmg/taxnewsflash/pdf/2026/02/tc-memo-2026-10.pdf
6.
https://www.govinfo.gov/content/pkg/USCOURTS-hid-1_14-cr-00826/pdf/USCOURTS-hid-1_14-cr-00826-0.pdf
7.
https://www.civilbeat.org/2025/11/dhhl-severs-ties-to-company-that-it-says-abandoned-homesteaders/
8.
http://www.smbiz.com/sbtc26.html
9.
https://www.supremecourt.gov/DocketPDF/24/24-793/339728/20250121124745222_24-
Petition.pdf
10.
https://www.justice.gov/archives/opa/pr/hawaii-businessman-convicted-federal-tax-crimes-failing-report-millions-dollars-income
11.
https://cctaxlaw.com/2026/06/25/lessons-from-hee-v-commissioner-how-badges-offraud-turn-a-tax-dispute-into-a-fraud-case/
12.
http://oaoa.hawaii.gov/jud/opinions/ica/2008/ica28056sdo.htm
13.
http://oaoa.hawaii.gov/jud/21369am.pdf
14.
https://www.currentfederaltaxdevelopments.com
15.
http://oaoa.hawaii.gov/jud/23702.htm
16.
https://wirelessestimator.com/articles/2020/fcc-fines-sandwich-isles-and-its-founder-50-million-for-fraud/