It's a chapter that prosecutors, judges and others who know him never wanted - or expected - to see written.
New York's oldest registered sex offender is scheduled to move by week's end out of a Buffalo halfway house for released inmates and into a place of his own, after completing his latest term in state prison for molesting little girls.
The judge who sentenced him said at the time that she expected him to die behind bars.
But 10 years after his last arrest, as Sypnier prepared to shed the closely monitored lifestyle of the halfway house, its director warned that the spry and active Sypnier has not changed from the manipulator who used his grandfatherly charm to snare and rape victims as young as 4.
"Whether he's 100 or 101 or 105, the same person that was committing these crimes 10, 25, 30 years ago still exists today and has an unrepentant heart," said the Rev. Terry King, director of Grace House, which has twice taken Sypnier in from prison. "He is someone that we as parents, as members of the community, any community, really need to fear."
Six months after marking his 100th birthday in the Groveland Correctional Facility - becoming the first New York inmate to reach the milestone while incarcerated- the retired telephone company worker now says he wants to get to know the youngest members of a family that has disowned him.
"I'll tell them I never harmed any children," the father, grandfather and great-grandfather told his hometown newspaper, The Buffalo News.
A former daughter-in-law said he is not likely to get the chance.
"No one from the family plans to have any contact with him," Diane Sypnier said before ending a brief phone interview.
Being grandfatherly was how the 5-foot-5, 150-pound Sypnier found his victims, authorities say. After his most recent arrest at age 90 on charges of raping and sodomizing a 4-year-old girl and her 7-year-old sister, his neighbors in the suburb of Tonawanda recalled what appeared to be a kindly Sypnier offering rides to adults, handing out money to children so they could buy candy, and baby-sitting.
The victimized sisters called him "Grandpa," their mother said at the time, adding that it "was a total shock" when police showed her sexually explicit pictures of her girls found in Sypnier's apartment.
Sypnier's convictions date to 1987, when he was given three years' probation for sex abuse. He spent a year in prison for sexually abusing a minor in 1994. His neighbors in Tonawanda never knew of Sypnier's background because he was convicted before the adoption of laws requiring sex offenders to register with police.
A relative once came forward and said Sypnier had molested her while she was growing up, former Erie County prosecutor Frank Clark told the News. Authorities wonder what else might lie in Sypnier's past.
"People don't start to become pedophiles at 78," Erie County District Attorney Frank Sedita told the AP. "I call them vampires. ... This is something that's deep inside of them, and they won't want to stop doing this until they're dead."
But Sypnier says he is the victim of a miscarriage of justice, despite twice pleading guilty in the case involving the sisters.
"Those children crawled into bed with me because they were frightened, but there was never any sexual hanky-panky," Sypnier told the News.
Sypnier initially pleaded guilty in 2000 to two counts of rape, 15 counts of sodomy and endangering the welfare of a child for molesting the Tonawanda girls, as well as three in Buffalo. An appeals court threw out the conviction in 2002 after Sypnier claimed he was confused at the time, leading to another plea the following year to a lesser charge.
In sentencing Sypnier to as many as 10 years in prison, state Supreme Court Justice Penny Wolfgang told him she expected he would spend the rest of his life behind bars.
"The sheer notion of him wandering the streets unattended or unsupervised is a scary proposition," King said.
Sypnier was released on parole in 2007, only to be returned to prison in 2008 after failing to attend sex-offender counseling. He completed his term in November and will be on parole through 2012. Until then, he's forbidden from using e-mail, chat rooms or social networking sites, hanging around playgrounds or schools, or spending time in bars.
Instead, he spends his days watching television, cooking, socializing in the halfway house and attending programming, King said.
Sypnier's new address has not been disclosed, but the law requires him to enter it in the state's sex offender registry.
Although his age makes him New York's oldest registered sex offender, there is at least one older offender elsewhere. Bert Jackson of Utah is 103 and living under home confinement.