The FBI says he went to the corner of Clark and Addison in Wrigleyville Saturday night with what he thought was an explosives-filled backpack 20 minutes away from detonation.
The act came not long after Dave Matthews played his final song at Wrigley Field Saturday and tens of thousands of people spilled into the nearby area.
In fact, the explosives were fake and were given to him by an FBI informant.
Over the last several months, the Chicago man allegedly talked to an FBI informant in secretly recorded conversations about setting off car bombs, perhaps poison the city's water supply, and assassinate Mayor Daley.
FBI agents have been looking at this man more than a year, but it was within the last few months that they say he began to get serious about his plans.
Sami Samir Hassoun, 22, is a resident alien from Lebanon, coming to the country a few years ago. He lives above a series of stores in the 4700-block of N. Kedzie. Those who know Hassoun said he seemed like a pretty typical 22-year-old. They said he liked to date and considered becoming a doctor.
The baby-faced suspect smiled at his family in court Monday minutes before prosecutors outlined their case.
They say originally he talked only of using fake explosives and did not desire to hurt anyone. They wanted to see if his big talk would turn into an actual act.
The government says that thinking changed as Hassoun talked of his desire to make money by setting off real explosives at Wrigleyville and the Sears Tower, possibly contaminating the water supply, and also perhaps assassinating Mayor Richard Daley.
Aside from hoping he could be paid for setting off bombs, Hassoun reportedly hoped that it would set off "revolution" in Chicago and "take that Daley out and put some of our guys in," according to the criminal complaint against him.
Hours before his arrest, Hassoun's Facebook status read: "Sami Hassoun is working on his business strategy plan".
It was the Wrigleyville plot that the FBI says Hassoun attempted to carry out on Saturday, a night when the neighborhood was packed with people who attended the Dave Matthews concert.
"Most of the bars were crowded, Saturday nights, whether it's Dave Matthews or not," said Sluggers Sports Bar owner Steven Strauss, whose bar is next to the trash can where Hassoun placed the backpack. "It's a nightlife area - it would have been a terrible tragedy."
Hassoun is charged with placing what he though was an explosives-filled backpack in a trash can outside Slugger's sports bar across the street from Wrigley Field.
"Had this been real, I wouldn't be talking to you right now," said Zach Strauss of Sluggers. "It's just like a wake-up call. It's going to make us much more aware."
"He wanted to make a statement, and he wanted to replace the mayor of Chicago," said FBI Special Agent-In-Charge Robert Grant. "He was unhappy, obviously, with the way the city was running, but he was also unhappy with things that were happening in other parts of the world."
"His intent was to kill as many people as he could, and, in an area of town that was highly populated at that time of night, to create as much destruction as possible," said Grant.
The FBI says money and a change of mayor were the motivators of Hassoun's alleged acts and cannot find anything to suggest he was part of a larger terror group.
The FBI does not believe he is connected to a larger group and doesn't believe he has the skills to compromise the city's drinking water. Authorities say that one of Hassoun's goals was outlining what he thought was increasingly lax security in Chicago.
"He believed that security in the city was not what it once was, and he wanted to show that," said Assistant U.S. Attorney Joel Hammerman.
"It doesn't sound like he was really accurate because the security of the city worked very effectively to thwart his plan and hopefully it will work out that he goes to prison for a very long period of time," said Chicago Police Superintendent Jody Weis.
Grant says the public was never in danger thanks to a confidential informant who tipped his agents early and allowed them to step in and play the role of explosives provider.
Hassoun is said to have summed up his car bomb plot succinctly: "You park the car, and let it 'boom.'"
Hassoun's supporters left court Monday afternoon refusing to comment.
The head of the FBI in chicago said the confidential informant is the real hero in this story, bringing Hassoun to their attention more than a year ago.
If convicted, Hassoun faces five years to life in prison.