Australian chief financial officer Sabirhan Hasanoff stood before the New York judge who held his fate in her hands and apologised for abandoning a cushy family life and high-powered career to become an al-Qaeda spy.
The married father-of-three, who conducted a surveillance operation of the New York Stock Exchange for a potential terrorist attack, received little mercy.
US District Court Judge Kimba Wood sentenced Hasanoff on Monday to 18 years' jail in the US federal prison system, just two years below the maximum.
Hasanoff, 37, had hoped for a 13-year sentence after pleading guilty and being a model prisoner since his arrest in the United Arab Emirates in 2010 and extradition to New York.
"I'm very sorry for my conduct," Hasanoff told the Manhattan court, which was filled with 20 or so friends and family.
"I should have known better. There is no excuse.
"I apologise to the court, the country and my family, particularly my kids."
Hasanoff had entered guilty pleas to one count of providing and attempting to provide material support and resources to al-Qaeda and one count of conspiracy to provide material support and resources to the terror organisation.
Hasanoff's parents fled from Uzbekistan and settled in China where he was born, but soon after as an infant, the family immigrated to Australia, became citizens and settled in Adelaide.
The family moved to New York in his teenage years, Hasanoff worked hard at school, earned a business degree at New York's Baruch College, was hired by blue chip global accounting firms KPMG and PricewaterhouseCoopers and ended up as the chief financial officer of a company in Dubai.
Prosecutors and Hasanoff's lawyer, Joshua Dratel, who represented Australia's David Hicks when he was incarcerated at Guantanamo Bay, told the court how Hasanoff had fallen under the spell of Islamic extremists and how he had a desire to fight and die alongside other jihadists in Somalia, Afghanistan or Iraq.
To get there, Hasanoff agreed to help two Yemen-based al-Qaeda operatives, known as The Doctor and Suffian, including buying a remote control device used for detonating explosives, funnelling $US67,000 ($A72,000) in cash, as well as conducting surveillance of the New York Stock Exchange and preparing a report.
Hasanoff's arrest has taken a financial, emotional and physical toll on his family.
His wife was seven months pregnant when he was arrested in the UAE and, against doctors orders, she flew back to New York when Hasanoff was transferred under guard by US authorities.
His wife gave birth to their daughter prematurely in New York and their baby has neurological and heart problems.
Hasanoff's nine-year-old son and six-year-old daughter are receiving treatment for "separation anxiety and adjustment issues".
Judge Wood said while Hasanoff appeared to be "a charitable, loving, good family man none of that deterred him from planning to leave his family and die fighting jihad against Americans".
At one point Judge Wood asked Dratel if Hasanoff still believes the only way to the afterlife is through violent jihad.
Dratel replied: "There are two paths: One is legal, one is not. He is to stay to one that is legal."