[18] Cowan dropped out of school in year ten and began working odd jobs throughout his late teens, never holding down employment in one position for longer than a few months.
Cowan's theft and drug offences with the law had resulted in him performing community service duties at a public park in Brisbane.
On 5 December 1987, during one of these community service sessions, when Cowan was 18 years old, he took a 7-year-old child from the park into a toilet cubicle and raped him.
[23][24] Cowan's demeanour subsequent to the attack was casual, as he proceeded to watch television inside the childcare centre where he was performing maintenance duties.
[15] In September 1993, while living at a Darwin caravan park with his 18-year-old girlfriend Tracey Haneveld,[26][27] Cowan lured a 6-year-old boy into an abandoned car yard and raped him.
The boy was left in an abandoned car in the bush with a punctured lung due to the force of the act and several cuts.
Cowan initially denied his involvement, going to considerable length to portray his innocence by stating to the police, "I hope you catch the bastard".
[15] However, the officers quickly discovered that Cowan was the only man in the caravan park not to offer up a DNA sample after semen was found on the boy's discarded underwear.
Psychological assessments followed, and Cowan was deemed as a pathological liar who lived a "parasitic existence", relying mostly on his parents to support him.
[15] The psychologist also discovered a gross lack of awareness on behalf of Cowan, who believed that his victim "would not report the case" because he "probably enjoyed" the experience.
In March 2014, prior to his sentencing in the Morcombe case, Haneveld spoke to 60 Minutes about her relationship with him, which she claimed was full of infidelity on his part.
During the trial, Cowan stated to the sentencing judge that his "years of heavy poly drug use" was an explanation for his assault history.
"'After addressing him over some personal issues that were of great concern to us, including lying, our relationship began to become strained and eventually he moved out to his own flat and the rest is history.'"
He was ordered to attend a sexual offenders treatment program, and moved in with his pastor aunt and uncle, Jenny and Keith Philbrook, on the Sunshine Coast,[30] becoming a reformed Christian.
[33] On 7 December 2003, 13-year-old schoolboy Daniel Morcombe left his home and planned to catch the 1:35 pm bus to the Sunshine Plaza Shopping Centre for a haircut and to buy Christmas presents for his family, but he failed to return.
The replacement bus drove past Daniel, and shortly after, in just a three-minute time span, Cowan is believed to have abducted him.
[39] Moncrieff, Cowan's wife at the time, later admitted in court that she lied about her husband's whereabouts on the day of Morcombe's disappearance because she was "blinded by love".
[citation needed] A covert police operation that had been used in Canada drew the attention of an investigator involved in Morcombe's case.
[40][41] In this case, an undercover police officer, posing as a crime boss known as "Paul Fitzsimmons" or "Fitzy", befriended Cowan on a flight to Perth in April 2011.
In 2006, Cowan had admitted to police that he travelled on the road from which Morcombe disappeared on the same day, on his way to purchase marijuana from a drug dealer.
[47] The trial, at the Supreme Court of Queensland in the state's capital Brisbane, began on 10 February 2014[47] under Justice Roslyn Atkinson.
The undercover policeman posing as 'Arnold' agreed that the fake crime gang had "dangled a carrot in the form of big money in front of Cowan".
The psychologist who had assessed him after his second molestation conviction in 1993 claimed he was a pathological liar with low level psychopathic features or mild psychopathy indicating a severe lack of empathy.
Acquaintances of Cowan, particularly his ex-girlfriends, had described him as initially being "charming", seeming "confident" and as being "handsome", which made it easy for him to gain the trust of his victims.