Pamela Smart: 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 Gov. 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 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 Smart, had admitted to cheating with another woman. Devastated, she threw herself into her job as director of media for 11 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 teenage bad-boy pal, Pete Randall, broke into the Smart’s condo, ransacked it to make it look like a burglary and waited for Gregg Smart. They forced Smart to his knees, and with Randall holding a knife to his throat, Flynn fired one fatal shot into his head. Pamela Smart was 40 miles away at a school board meeting.      

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

A controversial plea bargain was struck with the kids. No charges were brought against Pierce 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 Smart.       

Pamela Smart was arrested on charges of accomplice to murder and conspiracy to commit 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 O.J. 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 Smart “the Ice Princess” and “the Black Widow.” They conducted phone polls and Smart look-alike 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 Smart. 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 Smart’s defense attorneys also failed her. They only called one friend to vouch for her 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.       

Twenty-eight years later, Smart, 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 who committed murder? They both won parole in 2015 and are free.        

I have visited and interviewed Smart several times. She has earned two master’s degrees in prison and helped countless inmates advance their education, and she 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 Gov. Sununu. More on this case next week. 

Diane Dimond’s exclusive interview with Smart was featured on Investigation Discovery’s three-night special beginning on Sunday, Aug. 19, at 10 p.m. EDT.  

Rockland County resident Diane Dimond is a journalist, author, and a regular contributing correspondent for the Investigation Discovery channel.  To find out more about Dimond, visit her website at

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