The feds say Masri, 27, was bound for Somalia on a suicide mission when the plot was interrupted.
The I-Team has obtained letters recently written by Masri, providing an unusual glimpse of life in solitary confinement: letters from Al Qaeda with love.
We begin on a YouTube channel that features pictures of men armed with rocket launchers and machine guns and bodies in the streets. The video is accompanied by a chant in Arabic.
A website operator recently received two letters from Masri. Following an 18-month investigation, Masri was arrested on August 3rd by the FBI's Joint Terrorism Task Force.
According to an FBI agent's affidavit, Masri "hoped to become a martyr by wearing a suicide vest."
"I am not naive," wrote Masri. "I am not saying a person should willingly plunge into a volcano and expect it to be cold."
The letters from Masri are handwritten. One dated late October, the other early November.
They begin with "peace be upon you" in Arabic, but urge friends to "avoid Arabic" when communicating with him because it arouses suspicion.
Masri lists his prisoner number at the Metro Correctional Center, where he has been since his summertime arrest on one count of attempting to provide material support to an arm of Al Qaeda and one count of plotting the use of a weapon of mass destruction outside the U.S. as part of a personal jihad - or holy war.
"I did go through a mental struggle of my own, which I know of prior to me being imprisoned," wrote Masri in a letter. "I was somewhat prepared for it..."
Masri never mentions the words 'jihad' or 'Al Qaeda' in his letters that seem more like Muslim manifestos.
"He's bought into this world view, and the more he's arrested, separated, isolated, rather than persuade him he's wrong, it reinforces this isolationist outlook that he alone is in that small group of people who have the truth," said DePaul terrorism expert and professor Tom Mockaitis.
In the current edition of Al Qaeda's official "Inspire" magazine, a page entitled: "Oh Allah, Free the Muslim Prisoners" has Shaker Masri on the short list.
In the magazine, Al Qaeda terrorists also explain why they targeted two Chicago synagogues with package bombs hidden in computer printer components in October.
Both synagogues were targeted because they are in "Obama's city," and one was cited as a "gay and lesbian" congregation.
Despite the connections, Masri is not charged in that plot, but is among a growing number of radical Chicago Islamists pursued by federal authorities.
"You have to submit to Allah - one, unconditionally; two, you will die; three, you will end in heaven or hell," wrote Masri in a letter. "You sometimes say to yourself: 'What was wrong with me and why didn't anyone stop me?'"
Masri's newly-retained attorney Thomas Durkin criticizes the government use of an undercover plant to gather evidence, an informant Durkin believes was trying to escape his own mounting legal problems.
Masri himself seems resigned to his fate.
"I am in solitary confinement. I am alone, which is a blessing," wrote Masri. "I cherish and thank Allah, for I am locked up 24 hours a day."
"More disturbing than any of the words is the absolute confidence with which he speaks," said Mockaitis.
Masri's mother, a Jordanian citizen, has hired a powerhouse legal team to help defend her son.
In addition to Durkin, Masri is represented by Linda Moreno from Miami and Joshua Dratel of New York, all of whom are considered heavyweights in the terrorist defense world.
The two letters were posted by the friend on a website for a brief period of time, which is where the I-Team found them. When the I-Team inquired, they were taken down.