As the retired broadcaster's marathon indecent assault and sexual touching trial entered its third month on Tuesday, his fifth and final complainant came face to face with his alleged assailant.
Jones, who has pleaded not guilty to 21 charges, did not make eye contact as his accuser entered the witness box.
The complainant told the NSW Local Court he had written to the longtime shock jock about his family's financial and personal difficulties when he was 13 years old.
Jones thanked him for a "sophisticated and articulate" letter and agreed to help, according to correspondence read aloud in court.
"I pioneered the expression 'struggle street', and I know that's where you and your mother live," the former Wallabies coach told the teen.
In one message, the court was told he suggested the teen not tell his mother certain information about their discussions of the financial issues.
In subsequent emails, Jones praised the teenager as special, a wonderful young man and "sent" him a big hug while repeatedly suggesting they meet up.
"I need to see you soon," the talkback titan wrote, according to the email chain.
He called the teenager the "most brilliant 13-year-old/14-year-old I've ever met" and said the high school student was always in his thoughts.
The complainant recalled having breakfast with Jones at his Circular Quay apartment, which his mother did not attend.
"You're a beautiful human being ... lots of love," Jones wrote to the then-14-year-old afterwards.
The complainant is expected to say the former ruler of Sydney's airwaves invited him to his house in the NSW Southern Highlands when he was 17.
Crown prosecutor Georgina Wright SC foreshadowed he would say Jones kissed him and touched him on the bottom without consent.
The teen did not initially report the incident but later wrote a note to his mother saying "someone in power did something they should not have," she said in her opening statement in August.
Jones's barrister Gabrielle Bashir SC has argued the teenager's mother encouraged him to make the complaint after learning Jones would no longer provide support to the family.
Her client maintains none of the alleged incidents occurred and insists the allegations against him are concocted.
"Rivalry, treachery, double dealing, money, hatred, desperation, opportunism and more are at the heart of this case," Ms Bashir declared in her opening statement.
Jones rose to prominence as the coach of the national men's rugby union team, the Wallabies, before turning to broadcasting in 1985, becoming one of the nation's most influential media figures.
He retired in 2020 - the same year as the last of the allegations against him is said to have taken place.
The trial, which began on August 3, is slated to continue into November and possibly December.
1800 RESPECT (1800 737 732)
National Sexual Abuse and Redress Support Service 1800 211 028
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