Published: Jul 01, 2013 11:35 AM EDT

JACKSONVILLE, Fla. (AP) - Donald James Smith has been in jail without bail for more than a week, charged with kidnapping and killing an eight-year-old Jacksonville girl.
    
But a troubling portrait of the 56-year-old Smith is emerging.
    
The Florida Times-Union (http://bit.ly/18qLHui) says accounts from Smith's childhood and adult acquaintances, neighbors and hundreds of pages of court records paint a picture of the career criminal as a young bully and a sexual deviant from at least his early 20s, as well as a lifelong charmer.
    
A neighbor told the paper that after Smith was released from jail in late May on a misdemeanor sex charge, Smith complimented the man's daughter.
    
"I said, 'You can stay the hell away from here,'" said Kevin Shivar, 46. He didn't see Smith again.
    
Four days later, Smith was arrested and charged with kidnapping and killing Cherish Perrywinkle. Jacksonville Sheriff's detectives say Smith befriended Cherish's mother as the family shopped at a dollar store, then offered to buy Cherish clothing and food at a Wal-Mart. An arrest affidavit said Smith told the mother he was going to buy food and took Cherish with him.
    
Authorities have not released details on how Cherish died or whether she was sexually abused. Her body was found near a church about three miles from the Wal-Mart.
    
His first recorded brush with trouble came in 1974 as a 17-year-old when police charged him with burning a stolen car. His crimes against children began three years later when he stopped his mother's green convertible outside a home where two girls, ages 5 and 8, were selling sodas and masturbated in front of them.
    
Smith failed in his attempt to plead insanity after his arrest. A judge deemed him a mentally disordered sex offender and he spent 18 months being treated in a state hospital. He was later sentenced to a year in jail and 10 years' probation.
    
Arrests followed for burglary, battery, stealing electricity, theft, worthless checks, auto theft and prowling, the latter coming a day after the out-of-wedlock birth of his only child, a son.
    
Smith's deviance resurfaced in late 1992 when he tried to lure a 13-year-old girl into his van near an elementary school, then hunted her down after she fled and hid in a culvert pipe.
    
"You'll have to come out some time," he said, according to court documents
    
Smith eventually gave up, but an hour later flashed a pornographic picture at two other girls, ages 13 and 14, and tried to lure them into the van in the same neighborhood. They fled and police later arrested Smith, whose 15-year prison sentence for attempted kidnapping and showing obscene materials to minors got cut to six years upon appeal.
    
Because of his continued trouble, Smith spent 1999 to 2002 under involuntary civil commitment after meeting the criteria of a violent sexual predator as part of the state's Jimmy Ryce Act. Prosecutors released Smith instead of holding a civil commitment trial, which could have led to his indefinite detention.
    
Smith spent four years in prison for burglary and a judge recommended he get drug treatment. Prosecutors dropped a 2008 child neglect charge after a teen who accused Smith of taking him to a crack den later recanted.
    
In 2009, Smith posed on the phone as a state child welfare worker and told the mother of a 9-year-old girl he was investigating allegations she'd been molested by her grandfather. Smith made obscene statements to the girl on the phone and police arrested him after tracing the call.
    
The girl's mother refused to let her fearful daughter testify and prosecutors dropped the felony charges to misdemeanors. Smith got two years in jail and not the 20-plus years he faced in prison.
    
The mother told the Times-Union that she believes Cherish Perrywinkle would be alive if she'd done more to thwart the plea deal.
    
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Information from: The (Jacksonville) Florida Times-Union, http://www.jacksonville.com

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