Last fall, Habibov hired Akhror Saidakhmetov, 19, to work at kiosks in Savannah, Georgia; Philadelphia and Chesapeake, Virginia.
Abdurasul Juraboev, 24, a Uzbekistan native and legal permanent U.S. resident, worked at the Gyro King restaurant in Brooklyn. He asked his boss whether he could leave this weekend because he was traveling.
Until their arrests Wednesday in connection with an alleged failed attempt to join ISIS in Syria, Saidakhmetov and Juraboev appeared to live the mundane lives of ordinary Brooklyn immigrants.
They also appeared careless in planning their alleged plot. One man, for instance, showed up at U.S. Homeland Security offices to apply for a travel document, authorities said. They sometimes communicated online because they believed it would be harder for authorities to trace.
Juraboev allegedly discussed assassinating President Barack Obama, according to the complaint. But he told an FBI agent that he "currently does not have the means or an imminent plan to do so."
Juraboev and Saidakhmetov, authorities said, planned to embark on the journey to Turkey on Wednesday.
'This is real'
One of them discussed the possibility of hijacking a commercial flight to Turkey and diverting it "to the Islamic State, so that the Islamic State would gain a plane," the complaint said. They also talked about joining the U.S. military in order to attack soldiers.
Juraboev and Saidakhmetov were arrested in New York; Habibov in Florida. They face charges that include attempting and conspiring to provide material support and resources to a foreign terrorist organization, the complaint said.
"This is real," New York Police Commissioner William Bratton told reporters. "This is the concern about the lone wolf inspired to act without ever going to the Middle East or the concern of once they get to the Mideast, acquire fighting skills, capabilities and then attempting to return to the country."
Saidakhmetov was arrested Wednesday at John F. Kennedy International Airport attempting to catch a flight to Turkey, authorities said.
Juraboev, who was to catch a later flight, was arrested at his home in Brooklyn. Habibov, who Bratton said "helped organize and finance" the operation, was in Jacksonville, Florida, when he was picked up.
In addition to threats against Obama, the suspects allegedly talked of killing U.S. law enforcement officers. Juraboev allegedly mentioned planting a bomb at Coney Island if ordered to do so by ISIS.
An FBI intelligence bulletin to state and local law enforcement urged officers to be vigilant for not only recruits, but people who may want to carry out attacks.
"These individuals highlight the continued interest among U.S.-based violent extremist to support designated terrorist organizations," the bulletin said.
Outside federal court in Brooklyn, attorney Adam Perlmutter, who represents Saidakhmetov, said his client will plead not guilty if indicted.
"This case really makes us question the federal government's approach ... to young Muslim men in America," he told reporters. "They are very ham-fisted tactics. There is no attempt to intervene, to speak, to explore, to understand. There's just the rush to prosecution, to arrest, and to conviction."
The arrests come at the same time that a federal jury in Brooklyn hears testimony in the trial against a Pakistani man
allegedly involved in a separate al Qaeda conspiracy to carry out attacks in New York and Europe.
In the case against the three Brooklyn men, court documents said two of them posted parts of their plans on an Uzbek-language website, believing that the communications would be harder to trace.
Saidakhmetov is from Kazakhstan and a legal permanent U.S. resident. Habibov, who is from Uzbekistan, was in the U.S. legally but overstayed his visa, police said. Authorities began trailing them in August 2014.
The three men lived in Brooklyn.
Talk of killing President Obama
Saidakhmetov and Juraboev were to appear in Brooklyn federal court later Wednesday; Habibov in federal court in Jacksonville.
The names of lawyers for Habibov and Juraboev were not immediately available.
In a conversation recorded by authorities, Saidakhmetov said that if he was unable to get travel documents to Syria, "I will just go out and buy a machine gun, AK-47, go out and shoot all police," according to the complaint.
Saidakhmetov told an informant that carrying a gun in the United States was legal.
"We will go and purchase one handgun ... then go and shoot one police officer," he is quoted as saying, according to the complaint. "Boom ...Then, we will take his gun, bullets and a bulletproof vest ... then, we will do the same with a couple of others."
He said, "Then we will go to the FBI headquarters, kill the FBI people."
In a written statement in the Uzbek language, Juraboev allegedly speaks of killing Obama for "Allah" but notes he doesn't have the means to do it.
"I also want to fight and sincerely become a martyr under the Islamic Caliphate," he states, using another name for ISIS.
On his journey, Saidakhmetov allegedly "proposed finding an excuse to gain access to the pilot's cabin and diverting the plane to the Islamic State, so that the Islamic State would gain a plane," the complaint said.
'Enemy of Allah'
In November, Juraboev and Saidakhmetov also expressed interest in joining the U.S. military in order to pass information to ISIS about American airstrikes against the terror group, the complaint said.
When Juraboev said he was skeptical that Saidakhmetov "could stay calm and avoid trouble in the military, (Saidakhmetov) responded that he could always open fire on American soldiers and kill as many of them as possible."
In another conversation, Juraboev allegedly criticized Saidakhmetov's plan to join the military, saying that "leaving for Syria would be the most feasible choice."
In intercepted online communication, Juraboev said his parents were in Uzbekistan.
"Sometimes they worship and practice Islam, sometimes they do idolatry," he said, according to the complaint. "My sisters are uncovered, lack knowledge of a religion. I wish they knew at least how to cover themselves up."
At one point, Juraboev called Obama "an enemy Of Allah," and says, "I will execute Obama."
On February 21, Juraboev sent his employer a text message: "Brother I want to leave my country next weekend. Because I have some problem. Is it possible or not? Sorry!"
Saidakhmetov allegedly told a confidential informant that he intended to wage jihad in Syria but that his mother -- fearful that he would do so -- took his passport. The suspect then said he would try to get his passport back by telling his mother that he was traveling to Uzbekistan to visit relatives.
On February 2, Saidakhmetov brazenly appeared at the Department of Homeland Security offices in Manhattan and filled out an application for a travel document and had his photograph and fingerprints taken, the complaint said.
Young people and ISIS
Saidakhmetov and a confidential informant at one time watched videos of ISIS training camps in Syria, the complaint said, adding that Saidakhmetov said he was going to "become a Mujahid on the path of Allah" in war-torn Mideast country.
The complaint said Saidakhmetov on February 19 purchased a round-trip ticket for $571 to travel from New York to Istanbul, Turkey, on Wednesday. He was to return on March 31.
In Brooklyn, the travel agent who sold him the ticket on February 19 said Saidakhmetov picked the cheaper flight with a connection in Kiev, Ukraine, rather than paying $900 for a direct flight to Turkey.
"There was nothing out the ordinary about the transaction or him," said the travel agent, who asked not to be identified. Saidakhmetov purchased the ticket using a New York State ID.
His flight on Ukraine International Airlines was to depart at 12:30 a.m. Wednesday.
Saidakhmetov had earlier told the informant -- who he believed was traveling with him -- that if detected at the airport he would "kill a police officer and use the officer's gun to shoot other law enforcement officers."
Young people are featured in the ISIS propaganda,
including a recent video showing boys in camouflage and ISIS bandanas learning hand-to-hand combat.
The militants have repeatedly promoted videos using high-level production techniques to celebrate their brutality. A short mash-up clip in September played like a trailer for an action movie, with slow-motion explosions and flames engulfing American troops.
"There's no question what we're combating with ISIL's (U.S. government acronym for ISIS) propaganda machine is something we have not seen before," U.S. State Department spokeswoman Jen Psaki told CNN. "It's something we need to do a lot more work on. We are seeing 90,000, I think, tweets a day that we're combating."