APRIL 7--When friends and family members gathered recently at the White House for a private celebration of Michelle Obama’s 50th birthday, one of the invited partygoers was a former paid FBI Mafia informant.

That same man attended February’s state dinner in honor of French President Francois Hollande. He was seated with his girlfriend at a table adjacent to President Barack Obama, who is likely unaware that, according to federal agents, his guest once interacted with members of four of New York City’s five organized crime families. He even secretly taped some of those wiseguys using a briefcase that FBI technicians outfitted with a recording device.

The high-profile Obama supporter was also on the dais atop the U.S. Capitol steps last year when the president was sworn in for a second term. He was seated in front of the chairman of the Joint Chiefs of Staff, two rows behind Beyonce and Jay Z, and about 20 feet from Eric Holder, the country’s top law enforcement officer. As head of the Department of Justice, Attorney General Holder leads an agency that once reported that Obama’s inauguration guest also had La Cosa Nostra contacts beyond Gotham, and engaged in “conversations with LCN members from other parts of the United States.”

The former mob snitch has become a regular in the White House, where he has met with the 44th president in the East Room, the Roosevelt Room, and the Oval Office. He has also attended Obama Christmas parties, speeches, policy announcements, and even watched a Super Bowl with the First Family (an evening the man has called “one of the highlights of my life”). During these gatherings, he has mingled with cabinet members, top Obama aides, military leaders, business executives, and members of Congress. His former confederates were a decidedly dicier lot: ex-convicts, extortionists, heroin traffickers, and mob henchmen. The man’s surreptitious recordings, FBI records show, aided his government handlers in the successful targeting of powerful Mafia figures with nicknames like Benny Eggs, Chin, Fritzy, Corky, and Baldy Dom.

Later this week, Obama will travel to New York and appear in a Manhattan hotel ballroom at the side of the man whom FBI agents primarily referred to as “CI-7”--short for confidential informant #7--in secret court filings. In those documents, investigators vouched for him as a reliable, productive, and accurate source of information about underworld figures.

The ex-informant has been one of Obama’s most unwavering backers, a cheerleader who has nightly bludgeoned the president’s Republican opponents in televised broadsides. For his part, Obama has sought the man’s counsel, embraced him publicly, and saluted his “commitment to fight injustice and inequality.” The president has even commented favorably on his friend’s svelte figure, the physical manifestation of a rehabilitation effort that coincided with Obama’s ascension to the White House. This radical makeover has brought the man wealth, a daily TV show, bespoke suits, a luxury Upper West Side apartment, and a spot on best seller lists.

Most importantly, he has the ear of the President of the United States, an equally remarkable and perplexing achievement for the former FBI asset known as “CI-7,” the Rev. Al Sharpton.

A lengthy investigation by The Smoking Gun has uncovered remarkable details about Sharpton’s past work as an informant for a joint organized crime task force comprised of FBI agents and NYPD detectives, as well as his dealings with an assortment of wiseguys.

Beginning in the mid-1980s and spanning several years, Sharpton’s cooperation was fraught with danger since the FBI’s principal targets were leaders of the Genovese crime family, the country’s largest and most feared Mafia outfit. In addition to aiding the FBI/NYPD task force, which was known as the “Genovese squad,” Sharpton’s cooperation extended to several other investigative agencies.

TSG’s account of Sharpton’s secret life as “CI-7” is based on hundreds of pages of confidential FBI affidavits, documents released by the bureau in response to Freedom of Information Act requests, court records, and extensive interviews with six members of the Genovese squad, as well as other law enforcement officials to whom the activist provided assistance.

Like almost every other FBI informant, Sharpton was solely an information source. The parameters of his cooperation did not include Sharpton ever surfacing publicly or testifying on a witness stand.

Genovese squad investigators--representing both the FBI and NYPD--recalled how Sharpton, now 59, deftly extracted information from wiseguys. In fact, one Gambino crime family figure became so comfortable with the protest leader that he spoke openly--during ten wired face-to-face meetings--about a wide range of mob business, from shylocking and extortions to death threats and the sanity of Vincent “Chin” Gigante, the Genovese boss who long feigned mental illness in a bid to deflect law enforcement scrutiny. As the mafioso expounded on these topics, Sharpton’s briefcase--a specially customized Hartmann model--recorded his every word.

Task force members, who were interviewed separately, spoke on the condition of anonymity when describing Sharpton’s work as an informant and the Genovese squad’s activities. Some of these investigators provided internal FBI documents to a reporter.

Records obtained by TSG show that information gathered by Sharpton was used by federal investigators to help secure court authorization to bug two Genovese family social clubs, including Gigante’s Greenwich Village headquarters, three autos used by crime family leaders, and more than a dozen phone lines. These listening devices and wiretaps were approved during the course of a major racketeering investigation targeting the Genovese family’s hierarchy.

A total of eight separate U.S. District Court judges--presiding in four federal jurisdictions--signed interception orders that were based on sworn FBI affidavits including information gathered by Sharpton. The phones bugged as a result of these court orders included two lines in Gigante’s Manhattan townhouse, the home phone of Genovese captain Dominick “Baldy Dom” Canterino, and the office lines of music industry power Morris Levy, a longtime Genovese family associate. The resulting surreptitious recordings were eventually used to help convict an assortment of Mafia members and associates.

Investigators also used Sharpton’s information in an application for a wiretap on the telephone in the Queens residence of Federico “Fritzy” Giovanelli, a Genovese soldier. Giovanelli was sentenced to 20 years in prison for racketeering following a trial during which those recordings were played for jurors. In a recent interview, the 82-year-old Giovanelli--now three years removed from his latest stint in federal custody--said that he was unaware that Sharpton contributed in any fashion to his phone’s bugging. He then jokingly chided a reporter for inquiring about the civil rights leader’s past. “Poor Sharpton, he cleaned up his life and you want to ruin him,” Giovanelli laughed.

While Sharpton’s acrimonious history with law enforcement--especially the NYPD--rankled some Genovese squad investigators, they nonetheless grudgingly acknowledged in interviews that the activist produced for those he would go on to frequently pillory.

Genovese squad members, however, did not share with Sharpton specific details about how they were using the information he was gathering for them. This is standard practice since FBI affidavits in support of wiretap applications are filed under seal by Department of Justice prosecutors. Still, Sharpton was briefed in advance of his undercover sorties, so he was well aware of the squad’s investigative interest in Gigante and his Mafia cronies.

Sharpton vehemently denies having worked as an FBI informant. He has alleged that claims of government cooperation were attempts by dark forces to stunt his aggressive brand of civil rights advocacy or, perhaps, get him killed. In his most recent book, “The Rejected Stone,” which hit best seller lists following its October 2013 publication, Sharpton claimed to have once been “set up by the government,” whose agents later leaked “false information” that “could have gotten me killed.” He added, “So I have been seriously tested in what I believe over the years.”

In an interview Saturday, Sharpton again denied working as a confidential informant, claiming that his prior cooperation with FBI agents was limited to efforts to prompt investigations of drug dealing in minority communities, as well as the swindling of black artists in the recording industry. He also repeatedly denied being “flipped” by federal agents in the course of an undercover operation. When asked specifically about his recording of the Gambino crime family member, Sharpton was noncommittal: “I’m not saying yes, I’m not saying no.”

If Sharpton’s account is to be believed, he was simply a concerned citizen who voluntarily (and briefly) joined arm-in-arm with federal agents, perhaps risking peril in the process. The other explanation for Sharpton’s cooperation--one that has uniformly been offered by knowledgeable law enforcement agents--presents the reverend in a less noble light. Worried that he could face criminal charges, Sharpton opted for the path of self-preservation and did what the FBI asked. Which is usually how someone is compelled to repeatedly record a gangster discussing murder, extortion, and loan sharking.

Sharpton spoke for an hour in an office at the House of Justice, his Harlem headquarters, where he had just finished addressing a crowd of about 200 people that included his two adult daughters and his second wife (from whom he has been separated for ten years). A few minutes into the interview, Sharpton asked, “Are you taping this?” A TSG reporter answered that he was not recording their interview, but had a digital recorder and wished to do so. Sharpton declined that request.

In the absence of any real examination/exhumation of Sharpton’s past involvement with the FBI and the Mafia, his denials have served the civil rights leader well. Scores of articles and broadcast reports about the Obama-era “rehabilitation” of Sharpton have mentioned his inflammatory past--Tawana Brawley, Crown Heights, Freddy’s Fashion Mart, and various anti-Semitic and homophobic statements. But his organized crime connections and related informant work have received no such scrutiny.

In a “60 Minutes” profile aired three months before the August 2011 launch of Sharpton’s MSNBC show, correspondent Lesley Stahl reported on the “tame” Sharpton’s metamorphosis from “loud mouth activist” to “trusted White House advisor who’s become the president’s go-to black leader.” As for prior underworld entanglements, those were quickly dispatched: “There were allegations of mob ties, never proved,” Stahl flatly declared.

As host of MSNBC’s “PoliticsNation,” Sharpton now reluctantly identifies himself as a member of the media, if not actually a journalist. He spends his time at 30 Rockefeller Plaza surrounded by reporters, editors, and researchers committed to accuracy and the exposure of those who violate the public trust. In fact, Sharpton himself delights in a daily feature that seeks to expose liars, hypocrites, and others engaged in deceit (his targets tend to be Republican opponents of the Obama administration). As he wraps this segment, Sharpton points his finger at the camera and addresses his quarry: “Nice try, but we gotcha!”

In addition to his MSNBC post, Sharpton heads the National Action Network, which describes itself as a “Christian activist organization.” Obama, who refers to Sharpton as “Rev” or “Reverend Al,” is scheduled to deliver a keynote address Friday at the group’s annual convention in New York City. Mayor Bill DeBlasio will preside Wednesday over the convention’s ribbon cutting ceremony, while Holder and three Obama cabinet secretaries will deliver speeches.

Sharpton has been a leading supporter of Holder, who spoke at the National Action Network’s 2012 convention and saluted the reverend for “your partnership, your friendship, and also for your tireless efforts to speak out for the voiceless, to stand up for the powerless, and to shine a light on the problems we must solve, and the promises we must fulfill.” Last Friday, Sharpton appeared on a panel at a Department of Justice forum led by Tony West, the agency’s third-ranking official. West thanked Sharpton for his “leadership, day in and day out, on issues of reconciliation and community restoration.”

According to its most recent IRS return, which Sharpton signed in mid-November 2013, the National Action Network pays him $241,402 annually for serving as president and CEO. In return for that hefty salary, Sharpton--who hosts a three-hour daily radio show in addition to his nightly cable TV program--reportedly works a 40-hour week for the not-for-profit (which lists unpaid tax liabilities totaling $813,576).

For longtime observers, the “new” Sharpton’s public prominence and West Wing access is bewildering considering that his history, mob ties included, could charitably be described as checkered. In fact, Obama has banished others guilty of lesser transgressions (see: Wright, Jeremiah).

Sharpton now calls himself a “refined agitator,” an activist no longer prone to incendiary language or careless provocations. Indeed, a Google check confirms that it has been years since he labeled a detractor a “faggot,” used the term “homos,” or derisively referred to Jewish diamond merchants.

* * *

As an “informant in development,” as one federal investigator referred to Sharpton, the protest leader was seen as an intriguing prospective source, since he had significant contacts in politics, boxing, and the music industry.

Before he was “flipped” in the course of an FBI sting operation in 1983, Sharpton had established relationships with promoter Don King, various elected officials, and several powerful New York hoodlums involved in concert promotion, record distribution, and talent management. At the time, the music business was “overrun by hustlers, con artists, black and white,” Sharpton recalled in his 1996 autobiography. A federal agent who was not part of the Genovese squad--but who also used Sharpton as an informant--recalled that “everyone was trying to mine” his music industry ties.

In fact, by any measure, Sharpton himself was a Mafia “associate,” the law enforcement designation given to mob affiliates who, while not initiated, work with and for crime family members. While occupying the lowest rung on the LCN org chart--which is topped by a boss-underboss-consigliere triumvirate--associates far outnumber “made” men, and play central roles in a crime family’s operation, from money-making pursuits to more violent endeavors.

For more than four years, the fact that Sharpton was working as an informant was known only to members of the Genovese squad and a small number of other law enforcement agents. As with any Mafia informant, protecting Sharpton’s identity was crucial to maintaining the viability of ongoing investigations. Not to mention keeping him alive.

For example, an episode recounted by TSG sources highlighted the sensitive nature of Sharpton’s cooperation with the FBI/NYPD task force.

In advance of seeking court authorization to bug a pair of Genovese family social clubs and a Cadillac used by Gigante and Canterino, a draft version of a wiretap affidavit was circulated for review within the Genovese squad, which operated from the FBI’s lower Manhattan headquarters. The 53-page document, which detailed the “probable cause” to believe that listening devices would yield incriminating conversations, concerned some investigators due to the degree to which the activities of Sharpton were described in the document.

While the affidavit prepared by FBI Agent Gerald King and a federal prosecutor only referred to Sharpton as “CI-7,” the document included the name of a Gambino mobster whom Sharpton taped, as well as the dates and details of five of their recorded meetings. Such specificity was problematic since the possibility existed that the affidavit’s finalized version could someday be turned over to defense lawyers in the discovery phase of a criminal trial.

Investigators fretted that Sharpton could easily be unmasked by the Gambino member, who, if ever questioned about his meetings with “CI-7,” would surely realize that Sharpton was the wired informant referred to in the FBI affidavit. That discovery, of course, could have placed Sharpton’s life in grave danger. The Gambino wiseguy, too, likely would have faced trouble, since he was recorded speaking about a wide range of Mafia matters, including Gigante’s illegal operations. The Genovese power--rightly paranoid about bugged phones and listening devices--famously forbid fellow gangsters from even speaking his name. In fact, if a wiseguy had to refer to Gigante during an in-person meeting, a quick stroke of the chin was the acceptable means of identification.

In response to concerns about the King affidavit, the draft, which a source provided to TSG, was rewritten to carefully shroud Sharpton’s work with government agents. The affidavit’s final version--which was submitted to two federal judges--no longer included the disclosure that “CI-7” had “consensually recorded his conversations” with a gangster. The wiseguy’s name was also deleted from the document, as was any reference to the Gambino family or the informant’s sex.

Instead, the revamped affidavit simply noted that “CI-7 reported” to the FBI various details of Genovese family rackets. The actual source of that valuable intelligence about Gigante & Co. had been carefully obscured. As were the details of how that information was obtained via Sharpton’s battery-powered valise.

But despite efforts like this to protect Sharpton, some details of his informant work leaked out in January 1988, when New York Newsday reported that the civil rights activist had cooperated with federal investigations targeting organized crime figures and Don King. Though he reportedly made incriminating admissions to the newspaper, Sharpton quickly issued vehement denials that he had snitched on anyone.

While acknowledging contact with law enforcement officials, Sharpton--then involved in the early stages of the Tawana Brawley hoax--said he sought the help of investigators to combat the crack cocaine epidemic ravaging New York’s poorest communities. Sharpton also claimed to have contacted agents (and pledged his assistance) after a Mafia associate allegedly threatened him over a music industry dispute.

Sharpton asserted that a phone installed in his Brooklyn apartment by federal investigators in mid-1987 was there to serve as a “hotline” for the public to report drug dealing. He flatly denied recording phone conversations at the direction of law enforcement agents. In one radio interview, Sharpton even declared, “We have an ethical thing against wiretapping.”

In fact, Sharpton had been cooperating with the U.S. Attorney’s Office in Brooklyn as part of an investigation targeting Don King. According to a source involved with that probe, federal agents “ran him for a couple of months,” during which time Sharpton “did some recordings” via his new home telephone. But the nascent Department of Justice operation was abruptly shuttered in the wake of the New York Newsday story.

The Brooklyn investigators were introduced to Sharpton in late-1987 by Joseph Spinelli, one of the reverend’s former FBI handlers (and one of the agents who initially secured his cooperation with the bureau). While Spinelli had left the FBI for another government post, he still helped facilitate Sharpton’s interaction with other investigators. “Joe was shopping him around,” one source recalled.

For example, in July 1987, Spinelli called a federal prosecutor in Los Angeles and offered Sharpton’s assistance with a matter the lawyer was handling. The case involved Salvatore Pisello, a mobbed-up music industry figure who had just been indicted for tax evasion (and whom Sharpton had previously accused of threatening his life).

Referring to Sharpton, ex-prosecutor Marvin Rudnick said in an interview, “I didn’t know who he was” when Spinelli called. In subsequent conversations with Rudnick, Sharpton provided information about Pisello and a related music industry matter that was being scrutinized by Justice Department investigators.

While Sharpton would not prove particularly helpful to Rudnick, the attorney clearly recalled his brief, unorthodox dealings with the New York activist. “I remember having to go to a pay phone to take the call because he didn’t want it to be traced,” Rudnick laughed.

* * *

So why did Sharpton agree to become an FBI informant? And why was he willing to risk the dangers inherent in such cooperation?

“He thought he didn’t have a choice,” one Genovese squad agent recalled.

In the course of an investigation being run by Spinelli and his partner John Pritchard, Sharpton was secretly recorded in meetings with an FBI undercover agent posing as a wealthy drug dealer seeking to promote boxing matches.

As previously reported, Colombo crime family captain Michael Franzese, who knew Sharpton, enlisted the activist’s help in connecting with Don King. Franzese and Sharpton were later surreptitiously filmed during one meeting with the undercover, while Sharpton and Daniel Pagano, a Genovese soldier, were recorded at another sit-down. Pagano’s father Joseph was a Genovese power deeply involved in the entertainment industry (and who also managed the crime family’s rackets in counties north of New York City).

During one meeting with Sharpton, the undercover agent offered to get him "pure coke" at $35,000 a kilo. As the phony drug kingpin spoke, Sharpton nodded his head and said, “I hear you.” When the undercover promised Sharpton a 10 percent finder’s fee if he could arrange the purchase of several kilos, the reverend referred to an unnamed buyer and said, “If he’s gonna do it, he’ll do it much more than that.” The FBI agent steered the conversation toward the possible procurement of cocaine, sources said, since investigators believed that Sharpton acquaintance Daniel Pagano--who was not present--was looking to consummate drug deals. Joseph Pagano, an East Harlem native who rose through a Genovese crew notorious for narcotics trafficking, spent nearly seven years in federal prison for heroin distribution.

While Sharpton did not explicitly offer to arrange a drug deal, some investigators thought his interaction with the undercover agent could be construed as a violation of federal conspiracy laws. Though an actual prosecution, an ex-FBI agent acknowledged, would have been “a reach,” agents decided to approach Sharpton and attempt to “flip” the activist, who was then shy of his 30th birthday. In light of Sharpton’s relationship with Don King, FBI agents wanted his help in connection with the bureau’s three-year-old boxing investigation, code named “Crown Royal” and headed by Spinelli and Pritchard.

The FBI agents confronted Sharpton with the undercover videos and warned that he could face criminal charges as a result of the secret recordings. Sharpton, of course, could have walked out and ran to King, Franzese, or Pagano and reported the FBI approach (and the fact that drug dealer “Victor Quintana” was actually a federal agent).

In subsequent denials that he had been “flipped,” Sharpton has contended that he stiffened in the face of the FBI agents, meeting their bluff with bluster and bravado. He claimed to have turned away Spinelli & Co., daring them to “Indict me” and “Prosecute.” Sharpton has complained that the seasoned investigators were “trying to sting me, entrap me…a young minister.”

In fact, Sharpton fell for the FBI ruse and agreed to cooperate, a far-reaching decision he made without input from a lawyer, according to sources. “I think there was some fear [of prosecution] on his part,” recalled a former federal agent. In a TSG interview, Sharpton claimed that he rebuffed the FBI agents, who, he added, threatened to serve him with a subpoena to testify before a federal grand jury investigating King. After being confronted by the bureau, Sharpton said he consulted with an attorney (whom he declined to identify).

Following bureau guidelines, agents formally opened a “137” informant file on Sharpton, a move that was approved by FBI supervisors, according to several sources. Agents anticipated using Sharpton in the “Crown Royal” case focusing on King, but during initial debriefings of their new recruit, it became clear that his contacts in the music business were equally appealing.

Sharpton had met James Brown in the mid-70s, and became extremely close to the R&B superstar. He worked for and traveled with the mercurial performer, married one of Brown’s backup singers, and wore the same processed hairdo as the entertainer. Like Brown, Sharpton would sometimes even wear a cowboy hat atop his tribute conk.

It was first through executives at Spring Records, a small Manhattan-based label affiliated with Brown, that Sharpton--who worked from the firm’s office--was introduced to various wiseguys, including Franzese. His circle of mob contacts would grow to include, among others, the Paganos, Carmine DeNoia, an imposing Pagano associate known as “Wassel,” and Joseph “Joe Bana” Buonanno, a Gambino crime family figure involved in record distribution and production.

At one point before he was “flipped,” Sharpton participated in a mob scheme to create a business front that would seek a share of lucrative Con Edison set-asides intended for minority-owned businesses. That deal, which involved garbage collection contracts, cratered when the power company determined that Sharpton’s silent partner was Genovese captain Matthew “Matty the Horse” Ianniello. Details of the Con Ed plot emerged at a federal criminal trial of Ianniello and his business partner Benjamin Cohen. It was Cohen, who worked across the hall from Spring Records, who recruited Sharpton for the mob garbage gambit.