Recently, the matter of insanity among judges came up through Sol Wachtler, former chief judge of the Court of Appeals of the State of New York, and Diane Kroupa, who sat on the United States Tax Court.  Each of these now ex-judges beclouded their respective benches.  Wachtler, who had claimed mental illness, copped a plea bargain, sparing the New York State Unified Court System a tidal wave of questions regarding the validity of his rulings.

I have speculated about Kroupa's objectivity in deciding tax cases while under examination by the IRS and while expecting indictment on criminal tax charges, a tax community sentiment in which I do not stand alone.

Quite unsurprisingly, per a plea agreement, Kroupa pleaded guilty before U.S. district judge Wilhelmina Wright on 21 October to one of the six tax crimes hanging over her.  (Robert Fackler, Kroupa's husband and co-defendant, had already pleaded guilty in the matter.)

As a tax professional, I found a number of aspects in Kroupa's plea allocution transcript quite interesting.  As likewise noted by Keith Fogg on his Procedurally Taxing blog, Judge Wright and Assistant U.S. Attorney Benjamin Langner meticulously questioned Kroupa, building the record to ensure, with ironclad security, that there will be no question whatsoever of Kroupa's complete and knowing understanding the significance of her guilty plea.

Imprimis, it is interesting that Kroupa, as a Tax Court judge, used the services of a tax return preparer for her own tax affairs:

Q. Is it true that you and Mr. Fackler, sometimes one or the other of you, then compiled those and provided them to your tax preparer?

A. Yes.

Judge Wright also cautioned that the guilty plea might cost Kroupa, as a United States citizen, her right to vote:

Q. Also, because you are a United States citizen and because you have been charged with a felony, if you plead guilty you may lose your right to vote, to hold public office, to serve on a jury, and to possess any kind of weapon or ammunition. Do you understand?

A. I do, Your Honor.

In this era, when citizenship is not a prerequisite for voter registration, perhaps Kroupa would have done better as an illegal alien.

Moreover, it seems that Kroupa, like Wachtler, is under treatment and medication for, among other things, a bipolar disorder:

[JUDGE WRIGHT]:  Now, I also have to ask you a few questions about drug use. When I say "drug," I mean any drug, so that could be prescription medication or over-the-counter medication that you might take. Are you under the influence of any drug or medication at this time?

[KROUPA]  Yes, Your Honor.

Q. Okay. You've taken --

(Defense counsel and defendant confer)

A. Excuse me, Your Honor. I misunderstood. I am not under the influence of any – it's not – my ability to understand what I am doing is not impaired.

Q. Okay. I'm going to ask you a little bit about the medication that you've taken over the past 24 hours. Would you tell me what type of medication that is.

A. Yes. I'm being treated for anxiety, depression, and bipolar II. I have six medications, prescribed medications, that I take. They are Depakote, which is for my bipolar II and my depression; Lamictal[.]

MR. KELLY [Defense Counsel]: Maybe you should spell them.

A. Would it be helpful if I spelled the names of the drugs?

[JUDGE WRIGHT]. It would be helpful.

A. Depakote is D-e-p-a-k-o-t-e. Lamictal, L-a-m-e-c-t-a-l [sic], I'm taking that for anxiety, bipolar II, and mood stabilizer. Wellbutrin, W-e-l-l-b-u-t-i-n [sic], it's for depression. Propra – I don't even know how to pronounce this. I'm just going to spell it.

[JUDGE WRIGHT]. You can just spell it.

A. P-r-o-p-r-a-n-o-l-o-l, which is for mood stabilizing and anxiety. Seroquel, S-e-r-o-q-u-e-l, I take for bipolar II, depression, and anxiety. And then Levothyroxine, L-e-v-o-t-h-y-r-o-x-i-n-e, I take that for a thyroid issue.

Q. Okay. So you've described several medications. Will any of that medication impair your ability to understand what we're doing here today?

A. No, Your Honor.

The fact that Kroupa's medication use was even mentioned seems to indicate that it had been discussed during the plea bargain negotiations, and if so, then as a mitigating factor asserted by her defense counsel.

Judge Wright is obviously concerned over the effects of Kroupa's misdeeds upon the public perceptions of, and respect for, the courts as an institution.

Judge Wright and AUSA Langner may or may not share my concerns regarding Kroupa's objectivity in deciding her cases, while Kroupa knew that a tax crime indictment against her and her husband was likely in the works. 

Per her plea allocution, Kroupa and her husband understated their joint income by approximately one million dollars, causing a tax loss to the government of approximately $450,000.  Knowing that this was Kroupa's price, my suspicions that she may have thrown some cases to the IRS in hopes of lenity have not abated.

Kenneth H. Ryesky, now a senior advisor in the U.S. desk of Ernst & Young's International Tax Services in Tel Aviv, is a lawyer who has taught business law and taxation at Queens College CUNY.  He formerly served as an attorney for the IRS.