He convinced them he needed loans in order to retrieve offshore funds, and persuaded others to invest in a film which promised to be lucrative.
Judge Moses said many of those on whom Monk preyed were single women going through difficult times in their lives.
"You are an articulate and persuasive person. These are good qualities but you have chosen to use them in a destructive and criminal way," the judge said.
"You have left a trail of anger, despair and hurt that time can never heal."
When Di Sinclaire met Monk she was grieving the death of her husband.
"For me to hand out money to someone I hardly knew was totally out of character and was a testimony to how seriously depressed and unhappy I had become," she told the court in her victim impact statement.
"Looking back, there was nothing about him that was real or true. Leister Monk's whole life was a lie and it's a measure of his intellect that he was able to keep up the stories, because while he was lying to me he was lying to many others at the same time."
She added: "Until I met him I'd never met anybody evil."
Jim Allison was left destitute as a result of Monk's offending and died before he could see him brought to justice. Mr Allison's daughter, Sarah Neill, spoke on his behalf.
"While our father was not physically assaulted by Mr Monk, we believe that the stress and anxiety caused by Mr Monk's actions contributed to our father's cardiovascular condition that ultimately killed him."
Mr Allison was reduced to living on a meagre income as a result of continuously loaning money to Monk between 1990 to 2002.
"His entire world-view was reduced to raising funds to fulfil Monk's empty promises of investment returns."
The court also heard from Elaine Dallimore, who entered into a relationship with Monk in 1993 when she was working at an Auckland TAB.
Monk persuaded her to allow him to be on credit and she reluctantly agreed.
"He showed me legal documentation of various substantial investments he had in New York as proof that he would be able to repay me. On the strength of that information I advanced the defendant more and more money."
She loaned him more than $108,000, borrowing against her house in Auckland, withdrawing from her credit card and borrowing from family and friends.
As a result she said she lost her job, was forced to sell her home and lost her superannuation fund.
"I was left in debt, and all my trust and confidence was destroyed."
Monk, who acted as his own lawyer, made a lengthy submission to the court in which he apologised to his victims.
He said his motivation had never been greed and his offending was entirely fuelled by his gambling habit.
"It [the money] invariably went to the TAB," he said.
"I was a compulsive gambler in the throws of what can best be described as an awful disease."
The court was told that Monk had previously been convicted of about 100 dishonesty offences and has been to prison four times since 1961.
