Boyle Strikes Again: Incarcerated Individual Subject to Delinquency Penalties Even Though Attorney Embezzled Funds and Failed To File His Tax Returns

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We have often discussed the reach of the 1985 Supreme Court case United States v. Boyle. Section 6651(a)(1) and (2) impose delinquency penalties for failing to file a tax return or pay a tax unless the taxpayer can establish that the failure was due to reasonable cause and not willful neglect.  Boyle essentially stands for the position that taxpayers have a nondelegable duty to be aware of tax deadlines. An agent’s incompetence or willful misconduct will not excuse the taxpayer from delinquency penalties.

Lindsay v US is the latest case to apply the principle.


Lindsay was incarcerated and executed a POA to Bertelson, an attorney, to manage his affairs, including filing his tax returns.  The attorney assured Lindsay he was doing so for the years 2012-15; instead he failed to file the returns and for good measure embezzled hundreds of thousands of dollars. The actions resulted in Lindsay receiving $705,414.61 in actual damages and $1 million in punitive damages.

Lindsay eventually filed his tax returns and paid over $425,000 in delinquency penalties. He filed a claim for refund; IRS rejected and he filed a suit in district court. The district court, contrary to the magistrate’s recommendation, granted the government’s motion to dismiss, citing Boyle as precluding a claim for relief. Following a timely appeal, the Fifth Circuit affirmed. In so doing it applied Boyle to Lindsay’s somewhat sympathetic circumstances:

Lindsay claims that he exercised ordinary business care and diligence by giving Bertelson his power of attorney and by directing Bertelson to file his income tax returns and to pay his taxes. Lindsay routinely asked Bertelson whether he was handling Lindsay’s tax obligations, and Bertelson said that he was. In Lindsay’s view, he has a reasonable cause for late filings and delayed payments because he used ordinary business care and prudence but was nevertheless unable to file his returns and pay his income taxes due to circumstances beyond his control, i.e., Bertelson’s malfeasance.

Lindsay’s position was rejected in BoyleBoyle established that taxpayers have a non-delegable duty to promptly file and pay their taxes. 469 U.S. at 249–50. Unlike cases where taxpayers seek and detrimentally rely on tax advice from experts, “one does not have to be a tax expert to know that tax returns have fixed filing dates and that taxes must be paid when they are due.” Id. at 251. Lindsay’s argument fails.

The opinion disposed of a couple of other of Lindsay’s arguments. He also raised the IRS’s own definition of unavoidable absence as excusing delinquency. Citing George v Comm’r, a 2019 TC Memo opinion that collects cases on the point, the Fifth Circuit panel emphasized that the mere fact of incarceration itself does not mean there was reasonable cause to miss deadlines.

Lindsay’s final argument was that  Boyle does not control in cases where a taxpayer is not “physically and mentally capable of knowing, remembering, and complying with a filing deadline.” The opinion stated that even if Boyle created an incapability exception he could have done more, “much like he conducted business and employed a CPA while incarcerated.” 


Lindsay, like many other taxpayers, is out of luck when it comes to trying to recover delinquency penalties that can be directly linked to an agent’s misconduct or incompetence. He did have some recourse, however, as he was awarded significant compensatory and punitive damages from his embezzling attorney. 

Avatar photo About Leslie Book

Professor Book is a Professor of Law at the Villanova University Charles Widger School of Law.


  1. Kenneth H. Ryesky, Esq. says

    Anymore, the increasing complexity of the tax laws has made tax preparation professionals an integral part of the tax compliance process for many if not most Americans (I have been preparing my own since I was 17 years old, with the occasional help of the software). Things have significantly changed since the days of Boyle; perhaps it is time to take another look at just what constitutes business prudence and absence of negligence.

    Some historical parallels can be found with the telegraph’s legal status. The earlier cases held steadfastly to the notion that the telegraph operator was an agent of the sender, and the sender was accordingly bound by the message sent by the telegraph operator. [E.g., Durkee v. Vermont Cent. R.R., 29 Vt. 127 (1856); Dunning v. Roberts, 3 Barbour (NY) 463 (1862); Western Union Tel. Co. v. Shotter, 71 Ga. 760 (1883); Ayer v. Western Union Tel. Co., 79 Maine 493, 10 A. 495 (1887).].

    But with the inequitable results of such a rule, and the reality that the telegraphy equipment (and the personnel who operated it) were beyond the sender’s dominion and control, the courts began to view the telegraph companies as independent contractors and hold them liable for mutated messages that occurred on their watch [E.g, Pepper v. Western Union Tel. Co., 87 Tenn, 554, 11 S.W. 783 (1889); Shingleur v. Western Union Tel. Co., 72 Miss. 1030, 18 S. 425 (1895); Mt. Gilead Oil Co. v. Western Union Tel. Co., 171 N.C. 705, 89 S.E. 21 (1916).].

    {My after-school job as a teenager was at a local independent pharmacy (remember them?) which got the Western Union teletype terminal after Western Union shut down its local office, so I had occasion to deliver Western Union telegrams along with the prescriptions.}.

    • If you have not read it you might enjoy the biography of Tax Court Judge Vasquez which the ABA Tax Section published last December. He also had the job of delivering telegraphs.

  2. Bob Kamman says

    Lindsay’s problems, of course, all started with Buddy. See

    –which explains how Buddy, the drug-detection dog, smelled something funny when Lindsay was the subject of a traffic stop out in the West Texas town of Junction. To make a long story short, Lindsey went to a federal prison for possession with intent to distribute methamphetamines. Not every federal prison is a “Club Fed,” but Lindsey likely had more access to documents and visitors than if he were at a maximum-security state prison like the infamous one at Huntsville, Texas.

    Note to Ken Ryesky: My father retired from a 50-year Western Union career that started when he was a 15-year-old messenger in the Chicago Loop. He worked his way up to a job that required Morse proficiency, in the 20’s. When the school forms asked for father’s occupation, it was “telegrapher.” I was allowed to hang around the one-man office occasionally, like when the national media came to Prescott, Arizona, for the opening of the Goldwater presidential campaign. Much of their copy was filed by teletype through WU, back then.

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