100: Judge the Problem for Yourself

Stella Case No. 100, Originally Published: 11 January 2006

Dating back to his days at NBC, before he moved to CBS in 1993, late-night talk show host David Letterman was plagued by a persistent stalker. Margaret Mary Ray became the subject of headlines and the brunt of more than a few jokes with her activities over the course of a decade, which included breaking into Letterman’s Connecticut home, stealing his car and introducing herself to a highway toll-taker as his wife.

Before she knelt in front of an oncoming train in western Colorado in 1998 to end her life, she had spent 10 months in prison and 14 months in a mental institution for stalking Letterman — and had moved on to stalking astronaut Story Musgrave.

Colleen Nestler, too, fantasizes a special connection with Letterman. In December 2005, though, that imaginary relationship soured, at least in her mind. Nestler, 59, sought a temporary restraining order, contending that Letterman harmed her with “bankruptsy [sic], mental cruelty and sleep deprivation” continuously since 1994, a period during which she lived in New Jersey; Brooklyn, N.Y.; Camden, Maine; and finally Santa Fe, N.M.

She checked off options on a form filed in New Mexico’s First Judicial District Court in Santa Fe to request that the TV personality be required to stay “at least 3 yards away” from her; not “threaten, harm, alarm or annoy” her or her family members; not block her in public places; and not phone or contact her.

Late Show with David Letterman’s long-time title card.

She additionally requested in her own handwriting that Letterman be ordered not to “Think of me, and RELEASE ME from his mental harassment & hammering” (her emphasis).

The relationship she has concocted in her mind did not involve delusions of phone calls or encounters in the physical world. It involves messages she contends Letterman communicated to her in code via his show after he moved from NBC to CBS in 1993 to host The Late Show With David Letterman — coded messages he sent to her, she said in her court filing, during every single show.

Among those “messages” she claims Letterman conveyed was a proposal of marriage when Letterman uttered, during a teaser for his show, “Marry me, Oprah” — referring to her by “the first of many code names,” in Nestler’s mind, rather than obviously referring to daytime talk show host Oprah Winfrey.

In a six-page, typewritten chronology of their “relationship,” which, as she relates it, began when she was married and living in Nevada, Nestler holds Letterman responsible as the “root cause” of her slide into bankruptcy. She contends Letterman used words, “jestures” and “eye expressions” — and even the songs of guests on his show — to send her messages and respond to her, and to urge her to train as his co-host.

She further describes following Letterman’s coded instructions, including staying awake through the night to watch other TV shows at his behest and moving to New York, only to receive the brushoff when he did not contact her at her hotel room or take her when he went on a Caribbean vacation.

Her story also ensnares Regis Philbin, Kathie Lee Gifford and Frasier star Kelsey Grammer, all of whom, she writes, also communicated with her through the TV and knew of her “relationship” with Letterman.

But while Ray’s delusions got her incarcerated, the judge in Nestler’s case has taken a different approach. Rather than do anything to try to discourage her and thereby protect Letterman from yet another stalker, Judge Daniel Sanchez instead affirmed her delusions by granting her request and issuing a restraining order.

Sanchez signed the order prohibiting Letterman from contacting her and requiring him to stay away from her — all of which, no doubt, Letterman would have no difficulty abiding by. The judge also directed the TV star to appear for a hearing later on whether to make the restraining order permanent, although Sanchez granted a motion by Letterman’s attorneys for an expedited hearing.

Letterman’s lawyers, understandably, want to quash the restraining order. Jim Jackoway, his Los Angeles attorney, calls the charges in Nestler’s complaint “obviously absurd and frivolous” and “an unfortunate abuse of the judicial process.”

“While Ms. Nestler may deserve compassion and assistance, allowing her to bring claims against Mr. Letterman is not in her interests or the interests of justice,” Letterman’s attorneys said in their motion challenging the restraining order. “Celebrities deserve protection of their reputation and legal rights when the occasional fan becomes dangerous or deluded.”

The judge’s move also has concerned at least one advocate for the mentally ill.

Ginny Wilson, a Santa Fe representative for the National Alliance for the Mentally Ill, won’t criticize Sanchez, but says she wants to use this situation as an opportunity to educate people about the signs of psychological problems. She calls Nestler’s application “fantastical.”

“It’s obvious in [the] story that the judge has made a mistake,” she says. “And [now] other judges or lawyers can see that a lapse in judgment can put a person in a public situation that could be dangerous for her. Maybe it will help a judge to recognize when a mentally ill person is attacking an organization or an individual out of their delusions.”

Sanchez says he doesn’t sign every temporary restraining order that comes before him, but will sign one when it’s warranted.

“If they make a proper pleading, then I grant it,” he said.

Perhaps, then, the judge has some delusions of his own.

In a follow-up hearing, Nestler said in court that “Should [Letterman] ever come to New Mexico — and let it be recorded in this court — if he comes near me or sends someone on his behalf, I will break their legs and establish proof of my story.”

“Break their legs?” asked a shocked Judge Sanchez, finally waking up.

“Yes, I will,” Nestler said. “It’s the only recourse I have for tangible proof.” Told to not make threats in court, Nestler continued, “It’s not a threat. I’m saying it mainly because I want the court to know I tried to avoid this. The man has plans to include me in his plans, and I refuse.”

A plan to include her in his plans? Now that’s planning!

“Who’s to stop him from taking a flight here?” she continued. “Who’s to stop him from dressing up in some disguise? He has intentions with me. He constantly harasses me. He’s a very powerful man. He’s into mind control. He’s into control and manipulation.”

Has he ever contacted her? Sanchez asked.

“He has called just to remind me to think of him by calling and hanging up,” she said. “It’s a trick he’s done. He will use any device at his hand that’s subtle and undetectable by any court of law.”

With that, Sanchez had finally had enough and voided his previous restraining order. It was in force for about two weeks.


You can look at this case in several ways. First, it’s a sad commentary about a very confused woman. Or it’s a cautionary tale of the silly things celebrities have to go through when they get famous.

Or you could find it funny — though surely Letterman doesn’t think so: in 2005 police in Montana uncovered a plot to kidnap Letterman’s young son — he simply must take stalkers seriously. But as far as the True Stella Awards is concerned, the point is this: very often in a frivolous court case, the problem isn’t just with the plaintiff, or their lawyer, or the jury. It’s the one charged with keeping them all in check: the judge.

It’s hard to be a good judge, and easy to be a bad one. Most county and state judges are elected, and too often elections come down to popularity contests, and expensive ones at that.

Does it sound like a good idea to elect judges based on name recognition? Does it sound smart to have judges owe favors to rich citizens who bankrolled their campaigns? Doesn’t it sound more rational for judges to be appointed based on their qualifications?

Voters can still have control, with the ability to recall judges for cause. But it’s time to choose the men and women who sit behind the bench by better criteria than “hey — that one sounds good” when voting.

It is ludicrous that Judge Sanchez granted a restraining order in this case — the basis was alleged “coded messages” and “mind control”?! By doing so, he not only bought into delusion, but reinforced the delusional thinking in the mind of an unfortunate, confused woman who will now be more difficult to treat since someone important “believed me; why don’t you?!”

Worse, he allowed a stalker to use the court as an instrument in the harassment of her victim. In this case, the victim could afford lawyers to appear in court thousands of miles away from his home. Most people aren’t so lucky.


  • “Letterman Lawyers: End Santa Fe Claim”, Santa Fe New Mexican, 21 December 2005.
  • “Letterman Seeks to Quash Restraining Order”, Reuters, 23 December 2005.
  • “Judge Voids Order Against Letterman”, Santa Fe New Mexican, 28 December 2005.
  • Various court filings and (for background) news archives.

Case Status

I couldn’t find any information on what ultimately happened to Nestler, but hopefully she got the help she needed. After 33 years of hosting late night TV talk shows, Letterman retired from the Late Show in May 2015.

My 2022 Thoughts on the Case

First, considering I didn’t number the cases from the start, I’m quite satisfied for this one to end up as Number 100.

Letterman continued to have trouble with stalkers and other issues. In 2005 police uncovered a plot to kidnap his son for a $5 million ransom. Someone who worked at his house was charged in the case — celebs seemingly can’t trust anyone! House painter Kelly Allen Frank pleaded guilty in a plea deal and was sentenced to 10 years in prison.

In late 2009, someone left a package in his car demanding $2 million or the blackmailer would reveal Letterman was having affairs with several staffers. Letterman called the district attorney, who said to deliver such a check, and then followed the person who picked it up. When a producer for CBS’s 48 Hours tried to deposit the check, he was arrested. Joe Halderman later pled guilty to extortion, but only served six months in jail, plus probation and community service. Letterman told of the attempt on his show — and confirmed that he was having such relationships with staff members.

It 2011, a death threat against Letterman was posted on a website frequented by Al-Qaeda supporters after Letterman joked about the death of an Al-Qaeda leader. Letterman talked about the threat on his show: “State Department authorities are looking into this. They’re not taking this lightly. They’re looking into it. They’re questioning, they’re interrogating, there’s an electronic trail,” he said, “but everybody knows it’s Leno.”

It’s sometimes rough being a celeb. At least the very successful can afford lawyers to help.


Regarding Case #99, of the woman with private health insurance from her job at Walmart that turned into a nightmare.

Lee, a law professor in Georgia: “The case is even more convoluted than you [stated]. One aspect concerns how well the Shanks’ lawyer understood all the ramifications of her legal situation. For instance, he should have known about the subrogation clause in her medical insurance and factored that into the Shanks’ understanding of the settlement offer. It’s part of his job, although it’s also certainly possible that he did understand the situation and that the Shanks were lucky to get a settlement at all from the defendant — $900,000 isn’t a great settlement for someone in Debbie’s plight, and it may be that the plaintiff’s evidence wasn’t particularly strong. If the trust set up for her care is truly irrevocable, Wal Mart can’t get to it, and Debbie can be discharged of any obligation to Wal Mart in bankruptcy.”

Nick, an attorney in California: “Something struck me as wrong upon reviewing the case summary: namely, that the attorney’s fees and court costs are chargeable out of a subrogation claim (meaning that Wal-Mart would be limited to the amount paid over for the injured party’s use). Her attorney had to be aware of the subrogation claim, and unless there was some intent to challenge the validity of the claim, Wal-Mart was immediately entitled to at least that portion of the $417,477 reasonably attributable to past medical expenses. I tend to blame her lawyer for much of this situation. You do not let a client agree to a settlement until you have explained to them exactly how much of it they will get to keep. If you let them sign while they may be operating under a mistaken impression as to what they will get out of the settlement, you have failed to discharge your duties [as legal counsel].”

Amy, a nurse in Queensland, Australia: “Never mind Wal-Mart, what about the fees and costs involved that caused her to lose over half of her settlement?? I am very curious to know how much her attorneys charged her, especially given the outrage expressed by her attorney over Wal-Mart’s actions (which are a total disgrace, so you don’t think I agree with their actions). How much is he charging her now, and how is this family going to pay? This woman’s medical ordeal is only just beginning — quadriplegics suffer innumerable complications owing to their immobility. Christopher Reeve is a prime example of the complications they experience — and he had the means to afford top-notch care. Shame on the attorneys who helped to bleed this family dry.”

Good observation, but let me clarify one point: I don’t know whether the attorney(s) who helped her win her case is the same attorney helping her now; my sources don’t say.

But not everyone agreed.

Chuck, a construction executive in Minnesota: “I’m sure you’re probably receive a lot more mail on this case than any other before it. [Not even close. -rc] Because for almost all of your previous cases I’ve agreed that there is an air of foolishness and incredulity that these people even have the gall to file the cases. This one is completely different. You aren’t including this one just because it involves Wal Mart, are you? Historically, this is always the case — whenever a company becomes overly successful there are people that, for one reason or another, think they shouldn’t be that successful and that there’s something wrong with that. I say this because I really don’t see how this comes even close to a ‘wild, outrageous or ridiculous’ lawsuit. I think this is a totally legitimate case that has merit. They are asking for money [twice] for the same occurrence. How then does this become a wild, outrageous or ridiculous lawsuit? Could it be so just because it is Wal Mart? I think this is exactly the reason.”

Gee, Chuck: you don’t happen to build stores for Walmart, do you?

I didn’t just hear from Walmart apologists, but also from a Wal-Mart slammer, who asked for permission to post the story on anti-Walmart web site. The answer was no; this isn’t about Walmart, and it’s rather silly to suggest that it is. I made my points quite clearly, and essentially everyone else understood that.

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3 Comments on “100: Judge the Problem for Yourself

  1. My initial response while reading this was recalling Margaret Mary (Margot Kidder) eyeing Maverick (Mel Gibson) and, since the movie came out in 1994, could well have been an in joke at the expense of marriage-hopeful stalkers.

    Letterman handled such things with kind humour, in my memory of him on TV. I learn from you that the original was incarcerated then committed suicide, a true demonstration of how really tough real life is for many who can’t wrap their brains around it. I can verify the risks fame of any strength brings in the form of glamour in the eyes of some beholders. So i wonder if the judge in the case wasn’t also wanting a touch of that fame fire?

  2. We need more resources for mental health in this country.

    Yep. Too many see suicide as the only way to get help. -rc

  3. Something a lot of people don’t realize, and which needs to be more widely known, is just how problematic frivolous restraining orders can be. They put an INSANE amount of restrictions on the target, and an applicant that has problematic motives for filing it can manipulate to get the target in trouble when they did no wrong. One major thing is that it puts the responsibility to adhere to it almost entirely on the person the order is issued against. As long as the applicant doesn’t do something like go to the target’s home or place of business, they can make plans to “accidentally” bump into them somewhere and it is ridiculously difficult for the target of the order to get out of the legal ramifications because the applicant doesn’t have to prove they were there innocently, the target of the order has to prove he was not actively trying to violate the order.

    What’s more, the issuing of restraining orders on false grounds, when they make the news, can make judges hesitant to issue orders in cases where they’re legitimately necessary, putting people at even more risk.

    Judges need to question every application for a restraining order they get. It doesn’t mean they doubt a legitimate case, it’s just that the only way to weed out the false ones is to dig as deep as they’re allowed on EVERY application, even the obvious ones. Had the judge asked deeper questions in this case, he might’ve clued in sooner.

    Excellent insights. -rc


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