William Billy Flynn: Murder, Prison, and Parole Release

Billy Flynn is the man who, at age 15, shot and killed 24-year-old Gregg Smart on May 1, 1990, inside Smart’s condominium in Derry, New Hampshire. He did it at the direction of Gregg’s wife, Pamela Smart, a 22-year-old school staffer who had begun a sexual relationship with him. Flynn pleaded guilty to second-degree murder, testified against Pamela Smart at her 1991 trial, served 25 years in prison, and was released on parole in June 2015.¹

How Flynn Got Pulled Into the Killing

In 1989 and 1990, Pamela Smart worked as a media and journalism coordinator at Winnacunnet High School in Hampton, New Hampshire. Flynn was a student there. Smart, then 22, began a sexual relationship with the 15-year-old. Prosecutors later argued she used her position of authority and the intimacy of the relationship to manipulate him into committing murder. Former Assistant Attorney General Paul Maggiotto said at trial that Smart “had used her sexual powers to influence Bill Flynn,” telling the teenager that her husband mistreated her and “deserved to die.”²

Flynn testified that Smart told him the only way they could be together was if he killed Gregg, and that she threatened to end the relationship if he refused. In his own words: “I didn’t want to kill Gregg. You know, I wanted to be with Pame. And that’s what I had to do to be with Pame.”² In 2021, an opinion piece argued publicly that Flynn should be described as a “child sex abuse victim” rather than a “teen lover,” given that he was a minor student and Smart was an adult in a position of authority over him.³

The Murder on Misty Morning Drive

On the evening of May 1, 1990, Flynn and 17-year-old Patrick “Pete” Randall entered the condominium Gregg and Pamela Smart shared on Misty Morning Drive in Derry. Two other teenagers were involved as well: Vance “J.R.” Lattime Jr. supplied the getaway car and a .38-caliber revolver taken from his father’s gun collection, and Raymond Fowler waited in the vehicle outside.²

Flynn and Randall ransacked the apartment to make the scene look like a burglary, then waited for Gregg to come home. When he arrived, Randall held a knife to Gregg’s throat and forced him to his knees. Flynn fired a hollow-point bullet from the .38-caliber revolver into the back of Gregg’s head at point-blank range, killing him.⁴⁵

Arrest, Plea, and Testimony Against Pamela Smart

Police initially treated the scene as a botched burglary, and the investigation stalled for weeks. The break came through Ralph Welch, a friend staying with the Lattime family. Welch told Vance Lattime Sr. that his son’s revolver had been taken and given to Flynn. Lattime Sr. brought the firearm to Seabrook police, and ballistics testing confirmed it was the murder weapon. Welch also told investigators that Pamela Smart had promised $500 to each of the teenagers from a life insurance policy later confirmed to be worth $140,000.²⁶

Flynn, Randall, and Lattime Jr. turned themselves in to Seabrook police on June 12, 1990, after briefly fleeing to Connecticut. In January 1991, Flynn pleaded guilty to second-degree murder, reduced from the original first-degree murder charge, in exchange for his testimony against Pamela Smart.⁷

Flynn’s testimony at Smart’s March 1991 trial was the emotional center of the prosecution’s case. He told the jury Smart said she “needed her husband killed” because she feared losing everything in a divorce, and that she threatened to leave him if he did not go through with it. Paul Maggiotto later described the testimony as “extremely powerful” and said Flynn appeared to undergo a “reawakening” on the stand with “incredible remorse.” Smart’s defense attorney, Mark Sisti, attacked the credibility of the teenage witnesses as a “deal with the devil,” arguing they would say anything to reduce their own sentences. Smart’s mother, Linda Wojas, said publicly that “Billy Flynn lied to save himself.”⁸

Sentence and Years in Prison

On August 19, 1992, Judge Kenneth McHugh of Rockingham County Superior Court sentenced Flynn to 28 years to life in prison, the term negotiated in his plea agreement. He was 16 at sentencing.⁹ One outlet separately reported his original sentence as 40 years to life, though other records consistently cite 28 years to life from the plea deal.¹⁰

In prison, Flynn earned a college degree and became certified as an electrician’s assistant. Multiple sources describe him as a model inmate with more than a decade of good behavior. He met a woman named Kelly in 2002 and later married her while incarcerated. In January 2008, Flynn appeared before Judge McHugh again to request a reduction in his minimum sentence. Senior Assistant Attorney General Susan Morrell opposed the request, arguing Flynn had already received the benefit of a plea bargain. The judge ultimately reduced his minimum term by three years.¹¹¹⁰

Parole and Release

On March 12, 2015, the New Hampshire Parole Board unanimously granted Flynn parole on his first attempt. He was 41 and participated by telephone from a minimum-security facility in Maine. Board member Donna Sytek called his record of incarceration “remarkable,” and the board cited his “decade of good behavior” and status as an “exemplary” inmate.¹²

Flynn expressed remorse to the board, saying, “I will always feel terrible about what happened 25 years ago. Parole will not change that.”¹³ Members of the Smart family attended. Gregg’s brother, Dean Smart, said he had “come to terms” with the release and hoped Flynn would use his second chance to “do something great” and “redeem himself.” The victim’s cousin, Val Fryatt, disagreed, saying, “Greg should have been here to watch the Smart family grow leaps and bounds but instead he is a memory we share with our children.”¹²

Flynn was released at approximately midnight on June 4, 2015, from the Maine facility where he had been held. Patrick Randall was released the same day from a halfway house in Manchester, New Hampshire. Board member Leslie Mendenhall advised Flynn at the hearing to live his new life “in peace” and “in quiet,” telling him, “Don’t let anybody know where you are.”¹⁴

Where Flynn Is Now

Flynn was released on lifetime parole. He moved to Maine with his wife, Kelly, and as of late 2016 was living in an upscale home on three and a half acres. He vowed to avoid the media, honoring a request from the Smart family. Little public information about his life after prison exists beyond those details.⁶⁸

The Three Other Teenagers

Flynn was not alone. All four teenagers who took part in the killing have been released from prison. Their outcomes varied with their roles and cooperation:

Patrick “Pete” Randall, who held the knife to Gregg Smart’s throat, pleaded guilty to second-degree murder. He was originally sentenced to 40 years to life (with 12 years of the minimum deferred), later reduced by three years. He was granted parole in April 2015 and released on June 4, 2015, alongside Flynn.¹⁵
Vance “J.R.” Lattime Jr., who supplied the getaway car and the gun, was sentenced to 18 years to life and had been paroled by 2014, according to some reports.⁷
Raymond Fowler, the driver, was sentenced to 15 to 30 years and released on parole in 2003.²

Why Pamela Smart Is Still in Prison

The contrast between Flynn’s outcome and Pamela Smart’s is the central tension of the case. On March 22, 1991, Smart was convicted of conspiracy to commit murder, being an accomplice to first-degree murder, and witness tampering. Under New Hampshire law, the accomplice charge carried a mandatory sentence of life in prison without the possibility of parole. She was 23 years old.⁷

Flynn, who pulled the trigger, served 25 years and walked free. Smart, who prosecutors said masterminded the killing, can never be paroled. She denied involvement for more than 30 years but publicly accepted responsibility for her husband’s death for the first time in a video released in June 2024.¹⁶¹⁷¹⁸¹⁹

1
WMUR. Billy Flynn Granted Parole 25 Years After Killing Gregg Smart
2
ABC News. Pamela Smart: Teen Lover Murdered Husband Decades Ago
3
Seacoast Online. Billy Flynn Was Child Sex Abuse Victim, Not Pamela Smart’s Teen Lover
4
ABC7. Pamela Smart Seeks to Overturn Conviction
5
Lane Memorial Library. Verdict: Guilty
6
Seacoast Online. Pamela Smart Case Update
7
CNN. Pamela Smart Case Timeline
8
New Hampshire Magazine. Pamela Smart: Innocent or Still Guilty
9
The New York Times. Teen-Ager Sentenced in Love Triangle Killing
10
Union Leader. 25 Years After Smart Murder, William Flynn and Patrick Randall Paroled From Prison
11
Lane Memorial Library. Tearful Billy at Smart Hearing
12
NHPR. Teen Killer of Pamela Smart’s Husband Granted Parole
13
The Guardian. Gunman in Pamela Smart Case Released From Prison
14
WMUR. Smart Murder Co-Conspirators Billy Flynn, Patrick Randall Released on Parole
15
Seacoast Online. Smart, Randall: Triggerman in Husband Murder
16
PBS NewsHour. Pamela Smart Takes Responsibility for Husband’s 1990 Killing for the First Time
17
WCAX. NH Governor Rejects Hearing for Pamela Smart
18
CNN. Pamela Smart Seeks to Overturn Conviction
19
Union Leader. Prosecutors Seek to Block Pamela Smart’s Habeas Corpus Petition