David Letterman extortion plot just latest drama in his life...

Saturday, October 3, 2009
See Letterman's on-air admission here on video
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• David Letterman reveals $2M extortion plot
• Bombshell comes as host rises in ratings game
• Extortion over sex with staffers only latest drama in Letterman's life
• Letterman fans forgive host's affairs
• Letterman extortion the story of a career jester's transgressions made public

Behind the laughs, David Letterman's life has been peppered with a scary collection of loonies and criminals.

Perhaps one of the darkest times in the talk show host's private life came in 2005 when cops uncovered a plot to kidnap Letterman's then 22-month-old son, Harry.

They arrested 43-year-old Montana handyman Kelly Allen Frank and charged him with plotting to break into the "Late Show" host's isolated 2,700-acre ranch and snatch Harry and the child's au pair. Frank wanted $5 million for their return.

Frank, who previously had served time for stalking and intimidating a woman, pleaded innocent at first but later cut a deal and copped to felony theft and other lesser charges. He was sent away for 10 years in July 2005.

Five months later, two weeks before Christmas, another wacko came out of the woodwork, this one in New Mexico.

Colleen Nestler went to a Santa Fe district judge with a complaint that sounded like a bad joke. She said Letterman was somehow expressing his desire for her through code words such as "Marry me, Oprah," signals, and eye gestures.

Dave's influence forced her to go bankrupt and caused her "mental cruelty" and "sleep deprivation," she claimed. The judge bought Nestler's complaint and granted her request to order Letterman to stay 9 feet away from her and "no longer think of her."

Letterman's lawyer quickly had the "absurd and frivolous" action rescinded.

The first and perhaps best known trouble-maker in Dave's life was Margaret Ray, a Connecticut woman who drew national attention in the late 1980s when she stole Dave's Porsche sports car and then claimed she was his wife when stopped at a New York tollbooth.

In 1993 Ray trespassed at Dave's New Canaan home and camped out on his tennis courts. She spent seven months behind bars for that violation.

A few years later Ray was arrested in Westfield, Ind., - near the Carmel home of Dave's mom, Dorothy - for allegedly trying to steal vitamins and a backpack from a store.

In 1998, the 46-year-old Ray knelt in front of a 100-car freight train near a small Colorado train and was killed. Letterman called her death "a sad end to a confused life."

lstandora@nydailynews.com

Related News

• Articles
• David Letterman reveals $2M extortion plot
• Bombshell comes as host rises in ratings game
• Extortion over sex with staffers only latest drama in Letterman's life
• Letterman fans forgive host's affairs
• Letterman extortion the story of a career jester's transgressions made public

Behind the laughs, David Letterman's life has been peppered with a scary collection of loonies and criminals.

Perhaps one of the darkest times in the talk show host's private life came in 2005 when cops uncovered a plot to kidnap Letterman's then 22-month-old son, Harry.

They arrested 43-year-old Montana handyman Kelly Allen Frank and charged him with plotting to break into the "Late Show" host's isolated 2,700-acre ranch and snatch Harry and the child's au pair. Frank wanted $5 million for their return.

Frank, who previously had served time for stalking and intimidating a woman, pleaded innocent at first but later cut a deal and copped to felony theft and other lesser charges. He was sent away for 10 years in July 2005.

Five months later, two weeks before Christmas, another wacko came out of the woodwork, this one in New Mexico.

Colleen Nestler went to a Santa Fe district judge with a complaint that sounded like a bad joke. She said Letterman was somehow expressing his desire for her through code words such as "Marry me, Oprah," signals, and eye gestures.

Dave's influence forced her to go bankrupt and caused her "mental cruelty" and "sleep deprivation," she claimed. The judge bought Nestler's complaint and granted her request to order Letterman to stay 9 feet away from her and "no longer think of her."

Letterman's lawyer quickly had the "absurd and frivolous" action rescinded.

The first and perhaps best known trouble-maker in Dave's life was Margaret Ray, a Connecticut woman who drew national attention in the late 1980s when she stole Dave's Porsche sports car and then claimed she was his wife when stopped at a New York tollbooth.

In 1993 Ray trespassed at Dave's New Canaan home and camped out on his tennis courts. She spent seven months behind bars for that violation.

A few years later Ray was arrested in Westfield, Ind., - near the Carmel home of Dave's mom, Dorothy - for allegedly trying to steal vitamins and a backpack from a store.

In 1998, the 46-year-old Ray knelt in front of a 100-car freight train near a small Colorado train and was killed. Letterman called her death "a sad end to a confused life."

lstandora@nydailynews.com

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9:37:27 AM
Oct 2, 2009

I think every celebrity has had some sort of an affair at some time or another. It's hard not to with so many parties and drunken nights away from your partner. The opportunities are there all the time, sometimes the strongest will gives in to temptation. The question is...who is not having sex in TV land, it's like trying to find a dinosaur. If your in the business long enough, it's just a matter of time.

Report Offensive Post blackbrass

9:39:34 AM
Oct 2, 2009

So besides being a corny comedian, dave is also a cheater. Ho hum. Never cared for him anyway. JAY LENO is way funnier!

Report Offensive Post brads77

10:35:15 AM
Oct 2, 2009

Breaking news! Celebrities get l a i d! A lot!

Report Offensive Post KraftPaper

10:50:24 AM
Oct 2, 2009

His wife didn't know after 23 years? What's Dave in the Secret Service?

Report Offensive Post Smiley Eyes

11:01:23 AM
Oct 2, 2009

Am I disappointed in Dave just a little? Yeah, sure, I am. I am, however, very impressed by the way he handled the situation. He didn't whine and cry and offer his sincere apologies to his beloved wife and son for having strayed. I get so sick of hearing those scripted mea culpas while the devoted wife stands by her man and the tearful liar tries to gain some sympathy. Will I continue to watch him? Of course. He's the most innovative comic force on TV and has been for the last however many years. And he's still Dave. I never thought he had a squeaky clean image as has been mentioned anyway. And he's not a governor or a president or a public official, so whatever he does privately has no bearing on how he performs his job.

Report Offensive Post Kirkland

11:44:05 AM
Oct 2, 2009

Where do you people come from with your ridiculous remarks. Mr. Letterman is a grown man. The women he had sex with were grown women. The man was not married. It apparently didn't bother his now wife so why let it bother you? Jealous?? As far as I'm concerned, he can do what he wants in his private life. Like none of you had sex before you got married??? And how many of you had sex with someone OTHER than your spouse AFTER you got married?? The only difference is, he's rich and someone is trying to get richer off of him. I'll continue to watch his show as I don't see what any of this has to do with his job.

Report Offensive Post jezoebel

12:41:50 PM
Oct 2, 2009

Regardless of what Dave did, extortion is a crime. This bum should be rot in jail.

Report Offensive Post SayWhat

7:18:51 PM
Oct 2, 2009

Who doesn't want to ***** their boss.

Report Offensive Post TMI

7:35:52 PM
Oct 2, 2009

This matter is between Mr. Letterman, his family, and the authorities. It is none of our business. If anything, we should all be quite irritated with the Today show for how biased and opinionated they feel compelled to report the news, good or bad. Currently, they are a clique of blood thirsty loonies that ruined my favorite show. They were quite final in their quick judgement of David Letterman, assuming that he was everything bad and puppydog tales. The first thing that they point out about Mr. Letterman at their site story is that he made a few jokes about Sarah Palin, Dick Cheney and the GOP. David Letterman's show hasn't changed, just the thinly veiled petty retribution that has become so Johnson era esque. Live long and prosper Dave, even if your wife divorces you for way more than she ever deserved. Two sides to every story and it goes both ways. I have personally been cheated on by every woman I have ever been involved with and now with the wide variety of social sites availab

Report Offensive Post LujackLvr

8:46:34 PM
Oct 2, 2009

I am saddened for David Letterman's wife & son. I have watched Mr Letterman's show for years & I find him to be very funny. I was wondering what happened to Stephanie...I think telling his audience what happened pops his extortionist's balloon...even if the audience was uneasy [which they seemed to be; unsure if Dave was joking], Dave regained control of the situation, however humiliating the situation might be, he seemed to be willing to take responsibility for doing thoughtless things & looking foolish...in my opinion, his extortionist looks foolish now.

Related Topics

• David Letterman
• Margaret Ray
• Kelly Frank
• Talk Shows

• Media
• Television
• Oprah Winfrey
• Montana

• Santa Fe
• Carmel
• New Canaan
• Westfield

Ads by Yahoo!

Refinance Now at 4.25% Fixed
$160,000 Mortgage for $633/mo. Free. No obligation. Get 4 quotes.
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Obama Urges Homeowners to Refinance
($200,000 Refinance under $1,059/mo) See Rates - No Credit Check Req.
(SeeRefinanceRates.com)

Obama Gives $31 Billion for Student Aid
Get Your Degree Now. Financial Aid & Scholarships are available.
(www.ClassesUSA.com)

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9:37:27 AM
Oct 2, 2009

I think every celebrity has had some sort of an affair at some time or another. It's hard not to with so many parties and drunken nights away from your partner. The opportunities are there all the time, sometimes the strongest will gives in to temptation. The question is...who is not having sex in TV land, it's like trying to find a dinosaur. If your in the business long enough, it's just a matter of time.

Report Offensive Post blackbrass

9:39:34 AM
Oct 2, 2009

So besides being a corny comedian, dave is also a cheater. Ho hum. Never cared for him anyway. JAY LENO is way funnier!

Report Offensive Post brads77

10:35:15 AM
Oct 2, 2009

Breaking news! Celebrities get l a i d! A lot!

Report Offensive Post KraftPaper

10:50:24 AM
Oct 2, 2009

His wife didn't know after 23 years? What's Dave in the Secret Service?

Report Offensive Post Smiley Eyes

11:01:23 AM
Oct 2, 2009

Am I disappointed in Dave just a little? Yeah, sure, I am. I am, however, very impressed by the way he handled the situation. He didn't whine and cry and offer his sincere apologies to his beloved wife and son for having strayed. I get so sick of hearing those scripted mea culpas while the devoted wife stands by her man and the tearful liar tries to gain some sympathy. Will I continue to watch him? Of course. He's the most innovative comic force on TV and has been for the last however many years. And he's still Dave. I never thought he had a squeaky clean image as has been mentioned anyway. And he's not a governor or a president or a public official, so whatever he does privately has no bearing on how he performs his job.

Report Offensive Post Kirkland

11:44:05 AM
Oct 2, 2009

Where do you people come from with your ridiculous remarks. Mr. Letterman is a grown man. The women he had sex with were grown women. The man was not married. It apparently didn't bother his now wife so why let it bother you? Jealous?? As far as I'm concerned, he can do what he wants in his private life. Like none of you had sex before you got married??? And how many of you had sex with someone OTHER than your spouse AFTER you got married?? The only difference is, he's rich and someone is trying to get richer off of him. I'll continue to watch his show as I don't see what any of this has to do with his job.

Report Offensive Post jezoebel

12:41:50 PM
Oct 2, 2009

Regardless of what Dave did, extortion is a crime. This bum should be rot in jail.

Report Offensive Post SayWhat

7:18:51 PM
Oct 2, 2009

Who doesn't want to ***** their boss.

Report Offensive Post TMI

7:35:52 PM
Oct 2, 2009

This matter is between Mr. Letterman, his family, and the authorities. It is none of our business. If anything, we should all be quite irritated with the Today show for how biased and opinionated they feel compelled to report the news, good or bad. Currently, they are a clique of blood thirsty loonies that ruined my favorite show. They were quite final in their quick judgement of David Letterman, assuming that he was everything bad and puppydog tales. The first thing that they point out about Mr. Letterman at their site story is that he made a few jokes about Sarah Palin, Dick Cheney and the GOP. David Letterman's show hasn't changed, just the thinly veiled petty retribution that has become so Johnson era esque. Live long and prosper Dave, even if your wife divorces you for way more than she ever deserved. Two sides to every story and it goes both ways. I have personally been cheated on by every woman I have ever been involved with and now with the wide variety of social sites availab

Report Offensive Post LujackLvr

8:46:34 PM
Oct 2, 2009

I am saddened for David Letterman's wife & son. I have watched Mr Letterman's show for years & I find him to be very funny. I was wondering what happened to Stephanie...I think telling his audience what happened pops his extortionist's balloon...even if the audience was uneasy [which they seemed to be; unsure if Dave was joking], Dave regained control of the situation, however humiliating the situation might be, he seemed to be willing to take responsibility for doing thoughtless things & looking foolish...in my opinion, his extortionist looks foolish now.

Report Offensive Post Click Here to see all comments or to Report Abuse function getRefererURL() { var url = location.href; if (url.indexOf('#community') > 0) { url = url.substring(0, url.indexOf('#community')); } if (url.charAt(url.length-1) == '/') { url = url.substring(0, url.length-1); } return url; } RECENT COMMENTS FROM DAILY NEWS READERS 13 comments | See All Comments » var forumMsgCount = 13; To comment, Register or Log In
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