Maggie Mae Bennett: Guilty Plea, Sentence, and 2019 Release

Maggie Mae Bennett is one of eight people convicted in the 1997 kidnapping and murder of 13-year-old Maryann Measles in New Milford, Connecticut. She pleaded guilty in 2004 to kidnapping and related charges under an agreement that required her to testify against her co-defendants, was sentenced in 2006 to 19 years in prison, and was released in October 2019 after earning sentence credits for good behavior and program participation. She is the only member of the group no longer incarcerated.¹

Her Role in the Murder of Maryann Measles

Maryann Measles disappeared on October 19, 1997, from her mother’s car in the parking lot of a Big Y supermarket in New Milford. Her mother had gone inside to shop and returned about ten minutes later to find her daughter gone. Maryann, a seventh-grader, had recently reported sexual encounters with two older men in her social circle, ages 19 and 21, and her mother had filed statutory rape charges against the 19-year-old earlier that month. The group of eight wanted to keep her from cooperating further with police; some of the women involved were also reportedly jealous that Maryann had been sexually involved with their boyfriends.²³

According to police reports, Bennett drove her white van to pick up co-defendant Alan “A.J.” Walter Jr. the day of the killing. She had already confronted Maryann at a downtown gazebo, getting “into Maryann’s face,” and threatened to kill her for going to police about Walter raping her. Walter later told investigators that everyone present, including Bennett, took turns hitting the girl.³

The group took Maryann to a remote stretch of River Road along the Housatonic. Court documents describe beatings, choking, and sexual assault by three men, with at least one attacker holding her underwater until she was unresponsive. Her cause of death was asphyxiation. The attackers bound her wrists and ankles with electrical tape, wrapped her in a blanket, and weighted her body with a chain, padlock, and cinderblock before dumping her in the river. Her remains were recovered on July 15, 1998, near a boat launch on Lake Lillinonah in Bridgewater.²⁴

Arrests did not come until October 2002, when all eight suspects were taken into custody. Litchfield County State’s Attorney David Shepack told a judge the group had “agreed among themselves to discourage” Maryann’s rape complaint “by whatever means necessary,” and that all eight conspirators were physically present during the killing.⁵

Her Guilty Plea and Cooperation Deal

On March 10, 2004, Bennett appeared before Judge Charles Gill in Litchfield Superior Court and pleaded guilty to five charges: conspiracy to commit first-degree kidnapping, first-degree kidnapping, risk of injury to a minor, tampering with a witness, and tampering with evidence. In exchange, prosecutors dropped a conspiracy to commit murder charge. She was not convicted of murder; her conviction rested on the kidnapping and related counts.⁶⁷

Bennett was the first of the eight defendants to agree to cooperate with the state. Under the agreement, she had to testify truthfully against the remaining six co-defendants; if she failed to do so, the deal could be revoked and she could face additional perjury charges. Her sentencing was deferred until the other cases were resolved. The agreement called for a 30-year term, suspended after 15 to 20 years in prison, followed by five years of probation, with the exact prison time left to the judge.⁶

Her 19-Year Sentence

On December 15, 2006, after the remaining cases had been resolved, Superior Court Judge Robert C. Brunetti sentenced Bennett to 19 years in prison.⁷

At the hearing, Maryann’s mother, Cindi Measles, acknowledged Bennett’s cooperation but did not credit it as remorse: “I understand she was the first one to agree to turn state’s evidence… That doesn’t change what happened. It just means she’s smarter than the rest.”¹

Why She Was Released in 2019

In June 2018, after roughly 17 years in custody, Bennett petitioned the Connecticut Board of Pardons and Paroles for early release. The board denied the petition after hearing from prosecutors and the victim’s family.⁸

She was released the following year through a separate mechanism. By October 10, 2019, she was out under Connecticut’s Risk Reduction Earned Credit program. Karen Martucci of the state Department of Correction confirmed Bennett had earned credit “for compliant behavior and positive program participation.”⁹

Under Connecticut General Statutes § 18-98e, inmates sentenced for crimes committed on or after October 1, 1994, can earn up to five days off their sentence per month by adhering to an offender accountability plan, participating in assigned programs, and maintaining good conduct. Good behavior alone is not enough; the inmate must also engage in programming. The credits are awarded at the correction commissioner’s discretion and can be revoked for misconduct.¹⁰

Maryann’s sister, Jennifer Johnson, told the News-Times after the release: “Apparently, a killer can earn ‘good time’ in prison. Sickening.”⁹

Where the Other Seven Defendants Stand

Bennett’s early release stands out because none of the others have joined her. The seven other people convicted in the case received substantially longer sentences, reflecting their murder convictions and varying degrees of cooperation. State’s Attorney Shepack characterized Walter as the ringleader.

Alan “A.J.” Walter Jr. pleaded guilty to felony murder in February 2004 and was sentenced to 60 years.¹
Keith Foster, the only defendant to go to trial, was convicted in 2006 on nine counts, including felony murder, conspiracy to commit murder, first-degree sexual assault, and three counts of first-degree kidnapping, and was sentenced to 110 years.¹¹
Jeffrey Boyette Jr. pleaded guilty in June 2004 to felony murder, first-degree kidnapping, first-degree sexual assault, and risk of injury, and received 50 years suspended after 25, plus 25 years of probation.¹²
Deaneric Dupas pleaded guilty to felony murder and two conspiracy counts and was sentenced to 47 years. Judge Brunetti denied a sentence reduction request in July 2007, citing the “heinous nature of this crime.”¹³
Ronald Rajcok, originally sentenced to 36 years, had his sentence increased to 42 years in early 2009 by a three-judge Sentence Review Division panel in a 2-1 decision, which concluded he had “ultimate control” over Maryann’s fate as the driver who transported her to the murder site.¹⁴
Dorothy Hallas pleaded guilty to felony murder, kidnapping conspiracy, and risk of injury to a minor, and was sentenced to 25 years with a maximum release date of October 2027.¹
June Bates Seger pleaded guilty in July 2006 under the Alford doctrine to felony murder, conspiracy to commit first-degree kidnapping, and tampering with a witness, and was sentenced to 30 years. The state parole board denied her request for early release in 2020.⁵¹⁵

Based on the most recent available reporting, Bennett remains the only one of the eight who is out of prison.

1
Hartford Courant. Woman Involved in Brutal Murder of Maryann Measles to Be Released From Prison Early
2
A&E. Middle Schooler Maryann Measles Friends Abducted and Killed Her
3
New Haven Register. Woman Admits Guilt in Murder of Girl, 13
4
NewsTimes. Maryann Measles Case Timeline
5
NewsTimes. Measles Suspect Takes Deal
6
Times Union. Second Measles Suspect Takes Deal
7
Hartford Courant. Final 2 Sentenced in Measles Killing
8
Greenwich Time. Parole Denied in 1997 New Milford Murder
9
San Francisco Chronicle. Sister of New Milford Murder Victim
10
Justia. Connecticut General Statutes § 18-98e
11
New Haven Register. Supreme Court Rejects Appeal in 1997 Murder
12
CT Post. New Milford Man Sentenced to 25 Years in Measles Murder
13
CT Insider. Killer’s Jail Sentence Will Stand
14
NewsTimes. Sentence Increased for Measles Killer
15
San Francisco Chronicle. Early Release Denied for Woman Tied to Murder