A wire-wearing FBI informant named Shaheed Hussain was used in a sting operation against four Muslim men charged with trying to blow up New York synagogues and shoot down military planes. (Elizabeth Williams/AP)

Days before his arrest in Pittsburgh last month, Khalifa Ali al-Akili posted a remarkable message on his Facebook page: A mysterious man who spoke often of jihad had tried to interest Akili in buying a gun, then later introduced him to a second man, whom Akili was assured was “all about the struggle.”

It smelled, Akili wrote on Facebook, like a setup.

“I had a feeling that I had just played out a part in some Hollywood movie where I had just been introduced to the leader of a ‘terrorist’ sleeper cell,” Akili wrote.

When he googled a phone number provided by the second man, it turned out to be to Shahed Hussain, one of the FBI’s most prolific and controversial informants for terrorism cases. Soon the sting was off; Akili was subsequently arrested on gun — not terrorism — charges, which he has denied.

It was a rare miss for Hussain, 55, who has played a wealthy, dapper member of a Pakistani terrorist group in several FBI operations over nearly a decade.

This role has inflamed Muslim and civil rights activists, who describe Hussain as an “agent provocateur,” and prompted harsh comments from the presiding judge in a 2010 case, who questioned his honesty and the aggressiveness of the FBI’s tactics.

“I believe beyond a shadow of a doubt that there would have been no crime here except the government instigated it, planned it and brought it to fruition,” said U.S. District Judge Colleen McMahon at the sentencing of four men from Newburgh, N.Y., convicted on terrorism charges. She added, “That does not mean there was no crime.”

Hussain declined to speak about his work for the FBI, saying in a brief phone interview, “I can’t say anything for security reasons.” The FBI declined to discuss Hussain or McMahon’s comments.

But the blown Pittsburgh sting and the voluminous court records from the 2010 case have provided rare insight into a tactic used increasingly by the FBI since the Sept. 11, 2001, attacks in which suspects are monitored almost from the beginning of plots and provided with means to help them carry them out. The targets in such stings have included Washington’s Metro subway system, the Pentagon and the U.S. Capitol.

There have been 138 terrorism or national security cases involving informants since 2001, and 51 of those have come over the past three years, according to the Center on National Security at Fordham Law School in New York. The center said the government secured convictions in 91 percent of those cases.

Law enforcement officials say stings are a vital tactic for heading off terrorism. But civil rights activists and others say the FBI has been identifying individuals with radical views who, despite brash talk, might have little ability to launch attacks without the government’s help.

“It almost seems like the government is creating a theatrical event that produces more fear in the community,” said Michael German, a senior policy counsel at the American Civil Liberties Union and a former FBI agent who worked undercover.

Yet in these terrorism stings, every attempted defense that has alleged entrapment by the government has failed, according to Fordham’s Center on National Security. The FBI said that record speaks volumes and rejected any suggestion that it has invented terrorist plots. “They present the idea,” FBI spokesman Kathleen Wright said of the targets of investigations. “It is not us coming up with these ideas.”

Officials said the subjects of these stings are the ones who first generate suspicion — by contacting terrorists overseas, attempting to secure weapons or speaking of a desire to commit violence.

One of the prosecutors in the 2010 case, Assistant U.S. Attorney Jason Halperin, said in court that confidential informants such as Hussain are an “important tool” for the FBI. “Mr. Hussain is Pakistani. He speaks Urdu. He speaks Pashto. He’s Muslim. He can read Arabic,” Halperin said. “All of these things make Mr. Hussain a very valuable asset for the FBI.”

The birth of an asset

In testimony for the 2010 terrorism case, for which Hussain appeared as a witness for the prosecution, he described himself as a member of a politically connected family in Pakistan who fled to the United States with his wife and children after he was falsely accused of murder during a government crackdown against the secular MQM party. He arrived on a fake British passport in 1994, Hussain testified.

In the years since, his relatives in Pakistan have transferred hundreds of thousands of dollars to him, allowing him and his family to acquire gas stations, a beverage center and a motel in Upstate New York, according to financial records produced in court. He also testified that former Pakistan prime minister Benazir Bhutto, during a trip to New York, gave his son $40,000 to buy a new car, but the judge, McMahon, questioned the veracity of the claim.

It was not the only time McMahon expressed doubts about Hussain’s honesty.

“By the end of the trial, the jury knew that Hussain had lied about his finances to at least two courts (the Northern District of New York and the Northern District Bankruptcy Court), lied to the Immigration and Naturalization Service, lied to the Town of Colonie and its school district about his residence, lied to potential customers of his motel, and lied to the IRS about his income at tax time,” wrote McMahon.

In late 2001, Hussain was arrested on federal fraud charges of helping immigrants illegally secure driver’s licenses. Hussain, who had been working as a translator for the Department of Motor Vehicles, faced a possible prison term and deportation to Pakistan. He pleaded guilty and, as part of his agreement with the government, cooperated with the FBI by going undercover to secure evidence against several former associates in the scheme, including his mistress.

Hussain excelled in this new role — a fact grudgingly accepted even by his detractors.

“Both his physical and emotional presence seemed impervious to chastisement, to exposure, to anything — nothing seemed to throw his casual defiance off course,” said Karen Greenberg, the director of Fordham’s Center on National Security, who has observed Hussain in court.

The bureau also has sent Hussain to London and Pakistan, where he infiltrated a terrorist training camp, according to court testimony.

In the summer of 2003, Hussain first adopted the persona of the suave, moneyed terrorist at the direction of the FBI. The object of the sting was Yassin Aref, an Iraqi Kurd and the spiritual leader of an Albany mosque.

Aref was convicted of participating in a plot to launder funds from the sale of a shoulder-fired missile. Aref’s attorneys said he simply saw what he thought was a loan between Hussain and the owner of a struggling pizza parlor who was also convicted. Aref and the owner of the pizza parlor were sentenced to 15 years in prison.

The informant at work

On another assignment for the FBI, Hussain went to Newburgh’s Masjid al-Ikhlas mosque 12 times before he met James Cromitie, a convert to Islam and a stocker at a Wal-Mart, in June 2008.

In a poor community, Hussain struck an odd figure, driving Hummers and BMWs and wearing designer clothes.

Salahuddin Muhammad, imam of the mosque, said in an interview that some people suspected that Hussain was an FBI informant. He was too eager to engage people in conversation about jihad, Muhammad said.

Cromitie, who attended the mosque infrequently, either didn’t hear of the suspicions of others or didn’t care.

Hussain later told the FBI that Cromitie said: “Look, brother, I might have done a lot of sin, but to die like a shaded (martyr), I will go to paradise . . . I want to do something to America.”

By July, Hussain had told Cromitie he was part of a Pakistani terrorist group. Cromitie, who had multiple drug convictions but no history of violence, said he wanted to join, according to the FBI’s debriefing of the informant.

During a November 2008 trip to Philadelphia with Hussain, which coincided with the terrorist attacks on several locations in Mumbai, India, Cromitie made some of his most incendiary statements.

Cromitie hadn’t heard of the attacks, but Hussain pointed out that one of the targets in Mumbai was a Jewish center, according to transcripts of conversations that were secretly recorded and later played in court.

“I’d like to get a synagogue,” Cromitie said.

The judge later noted in a finding of fact that “whenever Hussain asked Cromitie to act on those sentiments — make a plan, pick a target, find recruits, introduce the [confidential informant] to like-minded brothers, procure guns and conduct surveillance — Cromitie did none of the above.”

McMahon said that at this point Hussain began to add “more worldly inducements” to the “offer of paradise” beginning with a BMW “but only after Cromitie had completed a mission.”

Closing the net

Hussain left for Pakistan on Dec. 18, 2008, and didn’t return to the United States for two months. While he was away, the FBI briefed officials at Stewart International Airport in New York on the investigation but assured them that “Cromitie was unlikely to commit an act without the support of the FBI source.”

Indeed, Cromitie said, “I just dropped everything,” according to the transcript of the conversation. But when Hussain returned, Cromitie’s enthusiasm was rekindled.

McMahon later wrote that “the court believes and specifically finds that it was about this time when Hussain offered Cromitie as much as a quarter million dollars to participate in a mission.”

Such an offer was not authorized by the FBI, the prosecutor told the court. Hussain denied making it, saying the reference to a specific amount of money was not intended to be literal. McMahon, in her sentencing, said she did not believe him.

After a surveillance drive around Stewart Air National Guard Base on Feb. 24, 2009, Cromitie cut off communication with Hussain for six weeks, he later testified. Cromitie pretended to have left town, although he was still in Newburgh.

On April 5, Cromitie called Hussain. “I have to try to make some money, brother,” Cromitie said.

“I told you. I can make you $250,000, but you don’t want it, brother. What can I tell you,” Hussain said.

Cromitie soon was back in.

On May 20, 2009, Hussain, Cromitie and three associates drove south from Newburgh carrying three duffel bags, each stuffed with nearly 40 pounds of explosives and 500 steel ball bearings to maximize casualties at a synagogue and a Jewish community center in the Bronx. After bombing them, the men planned to double back north to Stewart Air National Guard base near Newburgh to launch a stinger missile at parked military planes.

But the FBI had provided the bombs and the missile and had rendered them harmless.

All four Newburgh men were later convicted on terrorism charges in a jury trial and sentenced to 25 years in prison. They have appealed.

On the final drive to the Bronx, Hussain tried to get Cromitie to prime the bombs by following his instructions on which wires to connect, Hussain testified. But Cromitie and the others couldn’t figure it out, and Hussain had to stop the car and do it himself.

When they got to the Bronx, Hussain had to explain how to operate a car key fob so Cromitie could open the first of the pre-parked cars and plant the bomb.

Afterward, Hussain asked him if he had turned the bomb on. “I forgot,” Cromitie replied.

Hussain told him not to worry, it could still be detonated.

Cromitie then set off to plant the other two bombs, but he couldn’t open the trunk of the next car. Hussain told Cromitie by walkie-talkie to just put them in the back seat.

Hussain then signaled for the FBI to move in.

Staff writer Julie Tate contributed to this report.