A youth worker who watched a livestream of a six-year-old boy being raped and urged on the attacker has been jailed for 11 years.
Darren Williams, 44, sent messages to the rapist instructing him to "put the sound on" and "prove it's live" by "smacking" the victim and making him "say hi".
He sent messages telling chat room users that the rape, which took place in America, was about to be streamed and encouraged them to watch it.
Williams, of Blackwood, Newport, admitted encouraging or assisting the rape of a child and six charges of encouraging or assisting the showing of indecent images of children.
Judge Eleri Rees QC, the Recorder of Cardiff, jailed Williams for a total of 11 years at Cardiff Crown Court.
He was the first of four men, including a primary school teacher, to be sentenced in relation to the online chat room where the rape was streamed.
Laura Tams, specialist prosecutor at the Crown Prosecution Service, said: "Darren Williams clearly took sadistic pleasure in the pain and horrendous sexual abuse being inflicted on very young children.
"The prosecution built a case which showed how by watching and encouraging the abuse from behind his computer screen, Williams was guilty of encouraging the rape thousands of miles away.
"This conviction was made possible through close partnership working with the authorities both in this country and around the world."
Williams, who drove minibuses for children's charities in Gwent, was arrested in December 2015 and admitted seven offences.
The rapist who broadcast the attack, William Chandler Augusta from Pennsylvania, was detected by Canadian authorities and arrested in the US in February.
He was jailed for up to 30 years for a range of offences. Police officers in the US identified his victim and protective measures were taken.
The convictions of the four men follow an investigation by the National Crime Agency (NCA).
Primary school teacher Wayne Brookes, 43, of Weston-super-Mare, Somerset, will be sentenced for four offences at Bristol Crown Court on August 1.
Philip Crabtree, 35, of Newcastle-Under-Lyme, will be sentenced for 12 offences on a date to be set at Stoke Crown Court.
Christian Johnson Lueking, 36, of Raynes Park, London, admitted one offence of encouraging the showing of indecent images of children.
He will be sentenced at Kingston Crown Court on August 18.
Colin Radcliffe, operations manager at the NCA's child exploitation and online protection (CEOP) command, said: "Darren Williams drove children to activities where they would play sport and have fun together.
"As it's clear that he believes children can be horrifically abused for his pleasure his arrest was a vital intervention.
"These men thought they'd found a corner of the internet where they could avoid the consequences of participating in abuse.
"They were wrong and others like them should know NCA officers have skills and tools that mean no one seeking to harm children is safe from the law.
"Protecting children is an integral part of the NCA's mission and our officers are dedicated to ensuring people like these are brought to justice."