You can look at my coverage of Reed opinion to get my excuse for being slow on the August developments.
I Hate Crypto
I was intrigued by an August 6, 2026 ruling from Judge Philip Brimmer of the United States District Court for Colorado denying a motion by Jobadiah Sinclair Weeks to recover 8.6704622 Bitcoin (worth roughly $600,000 when he filed the motion in March). The Bitcoins had been seized in 2019 by IRS in an investigation that led to the indictment of Weeks and several others on December 5, 2019. The charges were conspiracy to commit wire fraud and conspiracy to offer and sell unregistered securities. There are over 600 entries in the Pacer docket for the case. It relates to BitClub Network which had been characterized as a Ponzi scheme. In July 2026 DOJ dropped the charges against Matthew Goettsche who seems to have been the mastermind. Weeks remains awaiting sentencing on his guilty plea. There is a website where you can get his side of the story. And this youtube video that you can spend nearly a half an hour of lifespan that you will never get back.
I still hate crypto, but this prosecution seems like a screw-up, although it may be a matter of elections having consequences.
When Setting A Precedent Doesn’t Get You Anything
Boechler PC is sort of a big deal, because there was a Supreme Court decision, which I covered back in 2022, and there are not that many Supreme Court decisions about tax. On June 5, 2015 IRS sent a letter to Boechler PC indicating there was a mismatch between the W-2s they filed and the corresponding Form 941s. (W-2’s report wages and withholdings. 941s are the payment forms. They need to reconcile.) There was no response, so IRS assessed a 10% intentional disregard penalty amounting to $19,250.37. On October 31, 2016 IRS sent a notice of intent to levy. Boechler PC requested a collection due process hearing. This would also be an opportunity to contest that penalty. There was some back and forth but ultimately the Office of Appeals sent them a letter confirming the proposed levy on July 28, 2017.
Boechler PC filed a petition with the Tax Court. Since there had been no previous opportunity to contest the liability in court, they would have that chance unlike a collection action from a notice of deficiency. The Tax Court received the petition on September 1, 2017 and it was postmarked August 29, 2017. That was day late so IRS moved for dismissal. Judge Carluzzo granted the IRS motion on February 15, 2019.
We should stop here and note that there are two lessons here. The first is to use a fucking payroll service, a well-established one. It is pretty improbable that they would create a mismatch between W-2s and 941s and if they did, the mismatch should end up being their problem not yours. The second is Reilly’s Seventeenth Law of Tax Planning – Don’t cut your deadlines close and use the US Mail with proof of mailing. Boechler PC violated the first half of the law.
Boechler PC appealed to the Eighth Circuit, which backed the Tax Court in its ruling on July 24, 2020. The idea is that the deadline is jurisdictional and the Tax Court has limited jurisdiction. So they don’t get to have an argument about why they should be allowed more time, which is referred to as “equitable tolling”. “Tolling” in this context means stopping the clock, so to speak. Normally that would have been the end of things, but this one went to the Supremes and they ruled on April 21, 2022 that:
“Section 6330(d)(1)’s 30-day time limit to file a petition for review of a collection due process determination is a nonjurisdictional deadline subject to equitable tolling.”
That seems like a big win for Boechler PC, but it has to go back to the Tax Court to consider how good the excuse was for being late. That ruling, on July 15, 2025, stated the excuse this way:
“Boechler is a sole practitioner law firm with limited staff. Its sole lawyer, Jeanette Boechler, is a single mother with a busy law practice and shared responsibility of caring for her elderly mother. The petition was mailed late because she miscalculated the date it was due.”
Note that if Ms. Boechler had followed the Seventeenth Law, miscalculating the due date by a day would not have been a problem. There were a lot of other demands on her time, including caring for her mother, but here is one that mystifies me a bit:
“Between August 17th and August 22nd of 2017, Ms. Boechler traveled to New York to assist her son in moving into his college dormitory. While there, she assisted him with his move and attended parent meetings at his new college.”
I have to admit that my ex-wife did that for our son, but I just didn’t get it. I also had a single mother and she helped me pack the trunk that got shipped to the college, but when it came time to go I just went. At any rate, Judge Buch ruled on July 15, 2025, that Boechler PC had not met either of the two requirements for equitable tolling:
“Boechler has satisfied neither of the requirements for equitable tolling. It did not establish that it diligently pursued its rights and did not establish any extraordinary circumstances outside of its control that prevented it from filing a timely petition. Accordingly, the petition is untimely and equitable tolling does not apply. Decision will be entered for the Commissioner.”
We’re still not done. It’s back to the Eighth Circuit which issued its ruling on August 10, 2026:
“BPC asserts that the “combined effect” of Boechler’s responsibilities as a caretaker, single mother, and sole practitioner amount to extraordinary circumstances that warrant equitable tolling. But the Tax Court found that Boechler, as BPC’s only attorney, “control her own workload,” and had co-counsel on several of her cases that were pending at the relevant time. And the record showed Boechler had other family members who were able to—and did—assist her with caregiving responsibilities. We see no clear error in these factual findings. See Chachanko, 935 F.3d at 629. And we agree this evidence was insufficient to support the conclusion that Boechler’s professional and personal circumstances were extraordinary such that they “stood in way” of BPC timely filing its petition for review. See Thompson, 919 F.3d at 1036.”
I am pretty sure they are using BPC to distinguish between Ms. Boechler and her eponymous corporation. That seems likely to be the end.
Of course, the IRS has to pick the collection file it put down a decade ago back up. The $19,250.37 has grown considerably since then. Assuming that they actually collect it, Boechler PC could ask for it back and the sue for refund in District Court.
In the end, though setting a Supreme Court precedent has not really done anything for Boechler PC, if the IRS has its act together enough to pursue the matter.
That phenomenon of the victor not getting any spoils from a Supreme Court opinion is not unprecedented. In 1991, the Supreme Court ruled in favor of John L Cheek. Cheek was an American Airlines pilot who believed that the income tax was unconstitutional. He indicated on his W-4 that he was exempt and did not file returns. He was indicted on multiple counts of willfully failing to file and willfully attempting to evade. The jury indicated that they had a difference of opinion about whether Cheek honestly and reasonably believed that he was not required to pay income taxes. The judge advised them:
“ person’s opinion that the tax laws violate his constitutional rights does not constitute a good faith misunderstanding of the law. Furthermore, a person’s disagreement with the government’s tax collection systems and policies does not constitute a good faith misunderstanding of the law.”
The judge followed that up the next day with “”n honest but unreasonable belief is not a defense and does not negate willfulness,” and “dvice or research resulting in the conclusion that wages of a privately employed person are not income or that the tax laws are unconstitutional is not objectively reasonable and cannot serve as the basis for a good faith misunderstanding of the law defense.”
The Supreme Court ruled that those instructions were wrong:
“However, it was error for the court to instruct 207*207 the jury that petitioner’s asserted beliefs that wages are not income and that he was not a taxpayer within the meaning of the Internal Revenue Code should not be considered by the jury in determining whether Cheek had acted willfully.”
Alternative tax thinkers were ecstatic to learn about the Cheek defense. There was a mini-industry of “tax professionals” who would write letters that you could use to show why you believed the income tax was unconstitutional. Among the people who purchased the letters for pretty short money was Kent Hovind who made the letter a big part of his innocence narrative, which I covered in 2015 when Bob Baty somehow found copies floating around on the internet.
It did not, however, help John L Cheek. On retrial, with revised instructions, he was convicted. He was sentenced to a year in prison and when he got back out American Airlines would not give him his job back. From what I can gather it has probably not led to a very large number of acquittals of others. When it came to Kent Hovind most of the counts in his indictment were for structuring which does not have a willfulness defense.
With respect to the Boechler opinion, it appears to me that the Tax Court is going to be pretty tough on people trying to take advantage of it, so the Seventeenth Law is going to stay in effect even for appeals of CDP hearings.
Another Deadline Case
Boechler is about the 30-day Tax Court deadline for CDP appeals. There is also a 90-day deadline to fight a statutory notice of deficiency. That is also being challenged with mixed results. The Eighth Circuit took it up again in Maniktala v Comm decided August 11, 2026. The Tax Court had not allowed a four month late petition by the couple. They will need to be looking at it again to consider equitable tolling.
There Is More
There are quite a few more August developments and it will be tough for me to get them done before this September becomes another one to remember. I am writing this on the last day of my seventy-fifth summer, so I have a lot to remember. Listen now to Jerry Orbach, singing about September well before Detective Lennie Briscoe was invented.
