For the backstory on Royalty Management Insurance Co., T.C. Memo. 2026-26, filed 3//26/26, see my blogpost “Capturing Captivity,” 9/16/24. 

But Judge Albert G. (“Scholar Al”) Lauber left himself some mopping-up, as he must consider “… whether we should sustain the 40% accuracy-related penalty that applies in the case of a tax underpayment attributable to a ‘nondisclosed noneconomic substance transaction.’ See §§ 6662(b)(6), (i), 7701(o); Royalty Mgmt., T.C. Memo. 2024-87, at *53–54.” T. C. Memo. 2026-26, at p.2.

The issue here is “adequate disclosure.” Did the return for year at issue let enough cat out of the bag?

” Section 7701(o) codifies the ‘economic substance’ doctrine. That provision, applicable to ‘any transaction to which the economic substance doctrine is relevant,’ provides a conjunctive test whereby a transaction is treated as having economic substance only if (1) the transaction changes in a meaningful way (apart from Federal income tax effects) the taxpayer’s economic position and (2) the taxpayer has a substantial purpose (apart from Federal income tax effects) for entering into the transaction. § 7701(o)(1). ‘The determination of whether the economic substance doctrine is relevant . . . shall be made in the same manner as if [section 7701(o)] had never been enacted.’ § 7701(o)(5)(C).” T. C. Memo. 2026-26, at p. 3.

Section 831(b) treatment isn’t a Congressional incentive to permit microcaptives to deduct insurance premiums that don’t provide insurance. Relevance of economic substance analysis isn’t forestalled by favorable treatment of real expenses that provide real insurance; nowhere does the IRC allow deduction of phony expenses.

And the “insureds” had no interest except tax dodging. 

As for disclosure, “Sheperd Royalty filed a return on Form 1120S, U.S. Income Tax Return for an S Corporation, for [year at issue]. In computing its net income, it claimed a deduction of $1,110,206 for ‘insurance’ expenses. That figure included the $1,099,900 of premiums at issue here, but those premiums were not broken out separately as a distinct item. Apart from listing a deduction for ‘insurance,’ Sheperd Royalty’s return disclosed no facts whatever—either in the return or in an attached statement—about the microcaptive insurance arrangement. Because Sheperd Royalty was a passthrough entity, the Sheperds reported their distributive shares of its income and deductions on Schedule E, Supplemental Income and Loss, included in their [year at issue] joint return. But their individual return likewise disclosed no facts about the microcaptive insurance arrangement.” T. C. Memo. 2026-26, at p. 10. There wasn’t an iota of specific information about the microcaptive. 

Section 6662(i) enhanced chop sustained.

I said it back in 2022: “…dear reader, before you groan ‘Oh no, not another GA boondockery,’ know I said it first. But I have to blog it; you can stop reading now and ignore it.” See my blogpost “Price and Value,” 1/12/22.

Judge Albert G. (“Scholar Al”) Lauber is in the same unhappy boat as I. Making its third appearance in this my blog is Hancock County Land Acquisitions, LLC, Southeastern Argive Investments, LLC, Tax Matters Partner, T. C. Memo. 2026-28, filed 3/26/26. 

The Hancocks fold the discounted cash flow method of valuation when their appraiser who furnished the Form 8283 backup appraisal fails to testify on the trial. The sales-comparison method doesn’t help, as their argument that their land is too unique craters. There are 10 (count ’em, 10) sales close enough for Judge Scholar Al to find their $763K per acre valuation of these boondocks “an order of magnitude that is light years away” from any rational number. T. C. Memo. 2026-28, at p. 29. And the investor testimony the Hancocks proffered only proved the investors were buying tax write-offs.

The tax loss insurance the Hancocks bought was for their investors’ benefit, hence not a partnership expense and not deductible by the partnership. The Hancocks do get a $25K appraisal fee deduction, despite the appraiser having been retained by the promoter; the Hancocks were the beneficiary. They also get some additional title expenses. The rest of the claimed Section 162 partnership deductions are indocumentados. 

And as their trusty accountant also had a piece of the deal, reasonable reliance doesn’t offset the substantial understatement 20% chop Judge Scholar Al lays on whatever the gross valuation misstatement chop (no reasonable reliance offset for that) didn’t cover.

It’s a tale I’ve told many times: the injured party who settles out and finds that the award is entirely taxable. The 1996 Small Business Job Protection Act did eliminate the need for a tort judgment but left the personal physical injury or physical sickness requirement for Section 104 exclusion. This recognized the trend in the law towards no-fault and other statutory remedies that eliminated the need for a finding of fault. Ser my blogpost “The Egg and I,” 1/22/15.

Physical injury may have been at the core in Toni C. Perry, Docket No. 4647-25, filed 3/25/26, an off-the-bencher from Judge Nega, but the stip of settlement in her State law case didn’t make that clear enough.

“Pursuant to the settlement agreement, the lump sum that petitioner received was for a general release of all claims except for those related to her Connecticut Workers’ Compensation Commission Claim…. Petitioner presented evidence and testimony of physical injuries unrelated to this settlement and many predating the alleged date of the back injury she claims underlies the settlement. Petitioner did not testify or provide any evidence to show that any portion of the settlement proceeds were used or designated for amounts paid for medical care attributable to those injuries.” Transcript, at p. 7.

Workers’ Comp is the exclusive remedy for on-the-job physical injuries, except for employer intentionally-inflicted injuries or employer-created dangerous conditions.

Toni’s testimony shows she didn’t understand the settlement but that’s not the issue.

Toni is represented here by the Quinnipiac University Law School’s LITC. Who represented her in the PI case is not stated, but I won’t unload on him/her. CT has a high bar to avoid Comp exclusivity, and Toni’s employer has plenty of resources to fight a tort claim. Pleading physical injuries on the job will get a swift motion to dismiss for want of jurisdiction.

“Petitioner’s counsel argued that petitioner could just as easily sued for workers’ compensation. But see CONN. GEN. STAT. sec. 31-284(a) (2025); Suarez v. Dickmont Plastics Corp., 639 A.2d 507, 510 (Conn. 1994). They then continued [sic; probably should be “contended”] that this somehow supports their position that the settlement is not taxable under section 104. While the Court takes no position on the proper tax treatment of this alternative, it is clear that the lawsuit settled here did not give rise to proceeds that are eligible for exclusion under section 104(a)(2).” Transcript, at p. 8.