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John Gotti. Whitey Bulger. R. Kelly?

The disgraced R&B singer’s federal trial begins Wednesday in New York as he is accused of racketeering, a charge famously applied to mob leaders like Gotti and Bulger.

Robert Sylvester Kelly, 54, faces a bevy of accusations: one count of racketeering with 14 underlying acts, including kidnapping, forced labor and sex trafficking, as well as eight counts of violating the Mann Act, which prohibits sex trafficking across state lines.

Separately, he faces federal charges of sexual exploitation of children and other crimes by the US Northern District of Illinois and state charges in Illinois. He was previously acquitted of state child pornography charges in Illinois in 2008. Kelly has pleaded not guilty to all charges in New York and other jurisdictions.

The use of racketeering in this type of case is unusual, but former federal prosecutor Shanlon Wu praised it as a bold and creative use of the law.

“It’s a very aggressive use of (racketeering) actually, which I commend, because it’s recognizing that for someone to have been an alleged abuser of so many other people that they have to have help,” he said.

How racketeering charges work

NEW YORK, NY - JULY 14:  Singer R. Kelly attends the Ovadia & Sons front row during New York Fashion Week: Men's S/S 2016 at Skylight Clarkson Sq on July 14, 2015 in New York City.  (Photo by Michael Loccisano/Getty Images)
Hear decades of allegations against R. Kelly
04:09 - Source: CNN

Racketeering became a federal crime in 1970 under the Racketeer Influenced and Corrupt Organizations (RICO) Act, and the charge is best known as a tool to prosecute organized crime that affects interstate commerce. At the center of any racketeering case is the “enterprise,” the group entity carrying out the illegal conduct, such as the mafia.

In this case, the enterprise is Kelly and his entourage, as well as his “managers, bodyguards, drivers, personal assistants and runners,” according to the superseding indictment. Kelly is described as the leader of the enterprise.

“The purposes of the Enterprise were to promote R. Kelly’s music and the R. Kelly brand, to recruit women and girls to engage in illegal sexual activity with Kelly and to produce pornography, including child pornography,” the indictment states.

Kelly’s defense attorney has criticized this aspect of the case against his client.

“We look forward to the truth and the facts coming to light as the defense will continue to vigorously defend Mr. Kelly,” defense attorney Thomas Farinella said in a statement to CNN. “After all, the RICO ‘Enterprise’ is based on a series of independent relationships and events that the government is trying to patch together like different types of fabrics and trying to pass it off as silk.”

Kelly is charged with racketeering that has 14 underlying acts: one act of bribery, three acts of sexual exploitation of a child, one act of kidnapping, three acts of forced labor and six acts of violating the Mann Act. The alleged crimes stretch from 1994 up to December 2018 and are based on incidents involving six anonymous “Jane Does,” several of whom were underage.

The oldest incident is the bribery act, from August 30, 1994, which alleges that Kelly and his enterprise bribed a public employee to create a fake ID for Jane Doe #1. A source familiar with the matter confirmed to CNN that Jane Doe #1 is the late singer Aaliyah, who was 15 at the time and married Kelly that year.

To convict him of racketeering, prosecutors have to prove that Kelly committed at least two of these 14 underlying acts.

Charging Kelly with racketeering has a few benefits for prosecutors, CNN legal analyst Elie Honig explained.

For one, it allows them to charge a broader pattern of conduct that stretches over years and involves many participants. In addition, a racketeering case combines multiple victims’ stories into one trial, which can create a #MeToo-like dynamic. The trials of Bill Cosby and Harvey Weinstein, though not racketeering, showed that having more witnesses testify about a pattern of alleged sexual misconduct can have a powerful impact on a jury.

Moira Penza, a former federal prosecutor who led the racketeering case against the cult-like group Nxivm, said the racketeering charge makes this trial very different from Kelly’s previous one.

“Having the RICO (racketeering) charge, in particular, allows prosecutors to really give this aerial view over a long period of time at a very high level of who R. Kelly and his enterprise are, and the types of crimes that they’ve been committing and the ways in which they’ve committed those crimes – that’s a very different case,” Penza said. “You have a lot more evidence that is going to come in and be able to corroborate what the victims are saying.”

Kelly’s attorneys have taken issue with the government’s case for the same reasons. In an August 6 filing, they criticized prosecutors’ request to admit additional evidence about uncharged acts as unfair.

“The government has done nothing more than stitched together a series of events spanning over three decades in an attempt to create an irrefutable mirage of guilt as to Mr. Kelly which will make it impossible for him to receive a fair trial,” attorneys Farinella and Nicole Blank Becker wrote.

How the Mann Act works

Singer R. Kelly appears in court on March 22, 2019, for a hearing at the Leighton Criminal Court Building in Chicago.

Six of the racketeering acts and eight of the standalone charges against Kelly are based on violations of the Mann Act.

Once known as the “White-Slave Traffic Act,” the Mann Act was passed in 1910 and sought to criminalize what’s now known as human trafficking. The law initially criminalized transporting a woman or girl across state lines “for the purpose of prostitution or debauchery, or for any other immoral purpose.”

The vague language around an “immoral purpose” meant it was used to punish consensual sexual activity and common sex work, often against Black defendants.

Most infamously, the Black champion heavyweight boxer Jack Johnson was convicted by an all-White jury in 1913 under the Mann Act for transporting a White woman, reported to be his girlfriend, across state lines. He fled the country for several years before returning to serve just under a year in prison, and the conviction derailed his career and ruined his reputation. (Former President Donald Trump posthumously pardoned Johnson in 2018.)

The Mann Act has since been amended several times and now criminalizes transporting any person across state lines “with intent that such individual engage in prostitution, or in any sexual activity for which any person can be charged with a criminal offense.”

In Kelly’s case, some of these Mann Act violations are related to more serious offenses, such as aggravated criminal sexual abuse. However, three of the violations accuse Kelly of knowingly exposing Jane Doe #5 and Jane Doe #6 to herpes without informing them and getting their consent, which is a misdemeanor under public health laws in New York and California.

Wu said it was unusual to include misdemeanor public health violations in such a serious federal case. He theorized that prosecutors included these stigmatized allegations in the indictment mainly to show the extent of Kelly’s bad behavior. And if prosecutors hadn’t charged him with these violations, they may not have been allowed to introduce them in the case because of evidence rules.

“So by charging him with transmitting herpes without permission, it obviously adds to the image of just how indifferent he was to people’s lives,” Wu said.

Outside the racketeering accusations, Kelly also faces eight freestanding charges of Mann Act violations. Four of these charges relate to an incident with Jane Doe #5 in 2015, and four relate to incidents with Jane Doe #6 in May 2017 and February 2018. These are also addressed within the underlying acts of the racketeering charge.

Charging a defendant with these crimes on their own is essentially a backup plan in case the jury has a problem with the racketeering case. For example, in a mafia case, a defendant may explain away a shooting as part of a personal beef rather than connected to the racketeering enterprise, Honig explained.

That will be tricky to argue here, though, given that the enterprise is closely aligned with Kelly’s life and career.

CNN’s Sonia Moghe contributed to this report.