As the retired broadcaster's marathon indecent assault and sexual touching trial entered its third month on Tuesday, he came face to face with his fifth and final accuser.
Jones, who has pleaded not guilty to 21 charges, did not make eye contact as the man entered the witness box.
The complainant told a Sydney court he had written to the longtime shock jock about his family's financial and personal difficulties when he was aged 13.
Jones thanked him for a "sophisticated and articulate" letter and agreed to help, according to emails 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 wrote.
The court was told Jones praised the teenager as special and a wonderful young man and repeatedly suggested they meet up.
"I need to see you soon," the talkback titan wrote.
He called the teenager the "most brilliant 13-year-old/14-year-old I've ever met" in another effusive email.
"You're a beautiful human being ... lots of love," Jones wrote to the then-14-year-old after they had breakfast together without his mother present.
The veteran broadcaster told the teenager he had looked "wonderful, fresh, and bright" after another meal, saying "I can't believe you're 14 years old".
In their messages, the high school student continually expressed his gratitude to Jones for his generosity and support.
"Except for my nan, no one knows you are my friend, mentor, confidante," he wrote.
Jones advocated on the family's behalf and paid upwards of $90,000 to assist them with their issues over a couple of years, the court was told.
At times he suggested the teen not disclose certain information to his mother about their discussions related to the financial issues, which had caused her stress.
As the expenses mounted, Jones told the teenager the costs were "getting out of hand", and there would come a time when payments would need to end.
"You're mature enough to know there can't be an endless dripping tap," he wrote.
"That's just between you and me."
When the high school student offered to set up a repayment plan, the court was told he was rebuffed.
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 the complainant 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," Ms Wright 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.
The then-teenager's allegation relates to one of 21 incidents of indecent assault or sexual touching without consent that the 85-year-old is accused of committing against five men between 2003 and 2020.
Jones maintains none of the alleged incidents occurred and insists the allegations against him are concocted.
The trial, which began on August 3, is slated to continue into November.
1800 RESPECT (1800 737 732)
National Sexual Abuse and Redress Support Service 1800 211 028
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