When an 82-year-old Victorian man listed his $1.6 million family home for sale, Brian Wilson visited and befriended the retiree.
Wilson, 54, helped the man to move his belongings into a retirement home, paying for a skip to help dispose of his rubbish.
The elderly man, who said he "was not as sharp as he used to be", opened up to Wilson. He revealed the home he had sold, in Melbourne's southeast, was mortgage-free.
After the move, Wilson visited the man at his Rosebud retirement village, which was when his almost $2 million con began.
Between October 2018 and September 2019, Wilson swindled $1.929 million from the man, convincing him to invest in fake business ventures, including selling cleaning products, a car sale and water jet cutting machines.
Wilson used the victim's money to place bets on gambling websites Tabcorp, Sportsbet, Beteasy and Ladbrokes.
The victim was left totally devastated by the offending and previously told the court he would never recover.
Wilson faced Melbourne's County Court on Tuesday by video link, where he learned his fate after pleading guilty to nine charges of obtaining financial advantage by deception and two obtaining property by deception offences.
Judge Trevor Wraight said Wilson's offending against a vulnerable victim was sophisticated, deceptive and planned, as he jailed him for five years.
"Your dishonest conduct was calculated and sustained and can only be described as reprehensible," he told the court.
"You befriended an elderly man, who in his own words says that he was 'not as sharp as he used to be', and you completely took advantage of him."
Wilson, who has served 11 days in pre-sentence detention, must spend a minimum of three years behind bars before he will be eligible for parole.
He was ordered to pay back more than $1.5 million in victim compensation.