How Long a Prison Sentence is Enough?

A petition has been filed with the Governor of New Hampshire that breathes new life into an old and very sensational case. It asks Governor Chris Sununu to embrace this era’s evolved thinking on prison sentencing, specifically the sentence of life without parole.

A key section of the 695-page petition reads, “The New Hampshire Constitution’s goal of punishment being ‘to reform, not to exterminate’ warrants relief for Pamela Smart through commutation of her sentence to time served or to make her parole eligible.”

Pamela and Gregg Smart on their wedding day – May 1989

Pamela Smart was 21 when she made the biggest mistake of her life. She was a newlywed living in Derry, New Hampshire and her husband, Gregg, had admitted to cheating with another woman. Devastated, Pame threw herself into her job as director of media for eleven public schools.  She met a dreamy-eyed, almost 16-year-old student named Billy Flynn. He was a juvenile delinquent who stole vehicles, robbed people, fenced stolen goods and used drugs. Pame and Billy clicked. They liked the same music and he was attentive where her husband was not. In early 1990, they began a brief sexual affair.

True crime buffs will remember what happened next. Flynn and his teenaged bad-boy pal, Pete Randall, broke into the Smart’s condo, ransacked it to make it look like a burglary and waited for Gregg. They forced Smart to his knees and with Randall holding a knife to his throat Flynn fired one fatal shot into Gregg’s head. Pame was 40 miles away at a school board meeting.

Cecelia Pierce, Testifying 1991, Accepted a Media Deal For $100,000

Police had no leads until they learned of the affair from Pame’s intern, a student named Cecelia Pierce, who swore it was Pame who had devised the murder plot with her young lover. Detectives placed a wire on Cecelia and hoped to capture conversations proving Pame was the mastermind. The resulting tapes were of bad quality and barely audible in many spots but Pame was heard telling Cecelia to lie to police or they would all “go to jail.” Pame would later explain she was desperate for information and only pretending to know about the murder plot so Cecelia would reveal what she knew.

Flynn, Randall and two other teens who waited in the getaway car were arrested. They were, inexplicably, kept in adjacent cells for several months making it easy for them to coordinate their stories. The boys mistakenly believed they’d only have to serve time until they were 18 so they stayed silent. But when the prosecutor decided to try them as adults and pursue the death penalty they suddenly spoke and claimed Pame had concocted the crime, convinced them to kill so she and Billy could be together.

A controversial plea bargain was struck with the kids. No charges against Cecelia even though she had helped the boys try to get a gun and reduced sentences for Flynn and Randall. In exchange, they all agreed to testify against Pame.

Pamela and Billy Back in the Day – Testifying 1991

Pamela Smart was arrested on charges of accomplice and conspiracy to murder and witness tampering. She has always professed her innocence. She says Flynn committed murder in a fit of rage after she told him she loved her husband and their affair was over.

Years before OJ Simpson’s murder case, the Smart trial was America’s first nationally televised courtroom drama. The tiny New Hampshire town became the focus of unprecedented and relentless international media coverage. Weeks before the trial started reporters clogged the streets and blared the latest developments.

The media labeled Pame “the Ice Princess” and “the Black Widow.” They conducted phone polls, Pame look-a-like contests and headlined her probable guilt. It all, surely, tainted the jury pool. But Judge Douglas Gray refused to change the trial venue. He repeatedly denied motions and witnesses that could have helped Pame. Gray also failed to follow up on multiple reports of jury misconduct. He openly hoped that Clint Eastwood would portray him in the inevitable movie. (There were two movies made. Eastwood was in neither.)

After my thorough read of the trial transcript and after much investigation it’s clear that Pame’s defense attorneys also failed her. They only called one friend to vouch for Pame’s character. Their opening statement to the jury was lackluster, the closing statement downright embarrassing. Immediately after the verdict Judge Gray announced the mandatory sentence:  Life in prison with no possibility of parole – ever. Every appeal by Smart has been rejected.

Flynn Writes From Jail, “There (sic) afraid I’ll get on the stand and say she’s innocent…” But Cross Exam on This Not Allowed

28 years later and Pame, now 51, remains behind bars at the maximum-security women’s prison in Bedford Hills, New York. Her release date is 99/99/9999. As for Flynn and Randall, the pair that committed murder?  They both won parole in 2015 and are free.

I have visited and interviewed Pame several times. She has earned two Master’s degrees in prison, helped countless inmates advance their education and is active in prison culture and church activities. She asked me recently, “Even if people think I’m guilty, which I’m not, haven’t I served enough time?”

That is the question now before Governor Sununu.  More on this case next week.



  1. Diane Dimond on August 20, 2018 at 8:35 pm

    Facebook Friend Sue Cochran writes:

    Her sentence is inhumane and barbaric. NH states the sentence should fit the crime, and the person. The 4 boys all had police records, which were sealed at trial, even though they were charged as adults. Guilty or not, Pamela Smart has MORE than served her time. Enough already. Free her.

    • Diane Dimond on August 20, 2018 at 8:39 pm

      Facebook Friend Elizabeth Bennett replies:


  2. Diane Dimond on August 20, 2018 at 8:45 pm

    Facebook Friend Kathy Deaton writes:

    I am not sure she is guilty I watched the show last night wonderful job Diane Dimond

  3. Diane Dimond on August 20, 2018 at 8:45 pm

    Facebook Friend Tricia Minahan Marchlik writes:

    I watched that back in the day and always thought she talked Billy into the act in return for sex…it didn’t take much for a young teen to do whatever for that. The other guys just got included. Pam had a devious plan and had young boys carry it out. Even if Greg cheated, which I think was mentioned in the show, no one deserves that

  4. Diane Dimond on August 20, 2018 at 8:46 pm

    Facebook Friend Doreen Merrey Siskin writes:

    watching part 2 now Dianne ,,,,,,looking forward to your interview with her ,,I agree on the length of sentence for the boys

  5. Diane Dimond on August 20, 2018 at 8:46 pm

    Facebook Friend Mary Rivera writes:

    I don’t think she has served enough time no matter how many degrees she’s earned behind those walls she was a dangerous woman with one degree dangerous and reckless not only with her own family but with the young boys that went to prison charged in this crime if she didn’t have a sexual affair with the underaged boy she and her husband and her codefendants would’ve all been ok..

    • Stephanie on November 21, 2019 at 4:18 pm

      She is still dangerous to this day! She has not owned up to her involvement and guilt!

  6. Diane Dimond on August 20, 2018 at 8:46 pm

    Facebook Friend Linda Ellis writes:

    Diane Dimond After watching your excellent program last night, I get the distinct sense that she is a pathological liar. Sitting in jail these many years has caused her to believe her own lies and convinced herself she did no wrong. She should be paroled like the young adolescents who carried out her murderous plan though.

  7. Diane Dimond on August 20, 2018 at 8:47 pm

    Facebook Friend Ann O’Neill writes:

    Diane, I’m always glad when the mastermind gets more time than the dimwitted minions. Kids were corrupted and a young man died. Pamela Smart is just another narcissist, played to scary perfection by Nicole Kidman. Wish she could share a cell with Jodi Arias.

  8. Diane Dimond on August 20, 2018 at 8:47 pm

    Facebook Friend Robin Dorian writes:

    I covered her trial for A Current Affair and spent time with Greg’s family. It was all really sad.

  9. Diane Dimond on August 20, 2018 at 8:47 pm

    Facebook Friend Elizabeth Bennett writes:

    Pame’s sentence is barbaric and a miscarriage of justice. Set her free now!

  10. Diane Dimond on August 20, 2018 at 8:48 pm

    Facebook Friend Emily J. Affrunti writes:

    Pamela Smart is where she should be and for the time allotted. I have no sympathy for her whatsoever. She is a master manipulator.

  11. Diane Dimond on August 21, 2018 at 9:36 am

    Twitter Pal vickie vertel@vvertel writes:

    Yes! She needs to stay in prison! No parole!

  12. Diane Dimond on August 21, 2018 at 9:36 am

    Twitter Pal DLB @60bourbon writes

    NO PAROLE ….. she’s where she belongs until she dies

  13. Diane Dimond on August 21, 2018 at 9:36 am

    Twitter Pal ShirleyWhel07 writes:

    I always thought Pamela Smart Was guilty but not any more then the shooter She should have gotten parole cause if the kids get out she should get out
    I don’t think she thought the kids would really do it #ID

  14. Diane Dimond on August 21, 2018 at 9:37 am

    Twitter Pal SheilaCook3 writes:

    She took an innocent man’s life and she should pay with her life.

  15. Diane Dimond on August 21, 2018 at 1:48 pm

    Twitter Pal Vanessa Julia Lutz@AngelaMcCourt55 writes:

    No it isn’t fair, but there’s a good ‘ol boys element at work…try digging deeper into who knows who, I bet cronyism is rampant in that little Peyton Place.

  16. Diane Dimond on August 21, 2018 at 1:48 pm

    Twitter Pal PitchingAFit @PitchingAFit writes:

    “Real killers”?? Come on. “But for” is a legal concept you’re well aware of, Diane.
    But for the actions of #pamsmart #pamelasmart, Gregg would be alive and 3 boys wouldn’t have gone to prison. ALL the damage in this case dominoes off PAM’s choices. Esp the murder SHE wamted.

  17. Diane Dimond on August 21, 2018 at 1:52 pm

    Facebook Friend Takia Parham writes:

    Amen sis, redemption has to start somewhere //
    If she were a master manipulator you wouldn’t be able to call her a master manipulator SMH people’s logic is skewed. I’m sorry I think I have a perspective to say this since I’ve seen some negative comments here. Of this is how Americans treat a European woman in law I expect nothing more for a so called Black person in law. Tough conversation but worthy of conversation. We as a people need to do better with judgement and redemption.

  18. Diane Dimond on August 21, 2018 at 2:25 pm

    Reader Peggy Martin writes:

    I read your oped today in our local paper. I believe the judge was so offended by the seduction of a student by a teacher that he went nuts in his sentencing! Confessed murderers get 40 years.

    I would also like to point out the number of male teachers who seduce girl students. That number was rampant when I was in school 55 years ago and when my daughter was in school in the early 90’s, a teacher wrote love letters to a female student who showed them around school. The teacher was “let go” but found a job at another Iowa school. Like the Catholic priest abusers. They should all serve prison time or at least have teaching licensed revoked permanently.

    I think the judge was much more concerned with the sexual aspects of this offense than the murder.

    Peggy Martin, retired teacher

  19. Diane Dimond on August 22, 2018 at 10:22 am

    Facebook Friend George Barwood writes:

    I see no way to be sure of her guilt, I study a lot of wrongful convictions, so I know how co-defendants will lie to save themselves. I also don’t feel the prosecution theory is plausible, and putting it all together I would say I am quite firmly convinced Pamela Smart is innocent. Not 100%, that’s impossible, it’s impossible to be certain of innocence in a conspiracy allegation, but the proof was not there.

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