Federal agents and police arrested the founder of gay escort site Rentboy.com and five staffers today on charges of racketeering by promoting prostitution. The site is far from discreet—it hosts an annual "Hookies Awards" to honor practitioners of "the oldest profession" and executives have made numerous ill-advised boasts about its users' services—but the timing, and the involvement of the Department of Homeland Security, are confusing.

The site's name is British slang for a male prostitute. It was founded in 1997 by Jeffrey Davids, identified by the feds as Jeffrey Hurant. Since then, it has grown into an international, multi-million dollar business, hosting the Hookies annually, as well as the thrice-yearly dance and cabaret party Hustlaball. The site allows escorts to pay to post ads that, as the federal criminal complaint notes, include whether the escort is circumcised, what his penis size is, whether he requires condom use, what his preferred sex position(s) are, and what his "primary interests" are—options range from "vanilla" and "oral" to "diapers" and "fisting." There are also required fields for hourly rates and overnight rates.

The site boasts ads across the US and the UK and as far afield as Singapore, China, South Africa, and Brazil. According to the feds, it brings in 500,000 users daily and grossed $10 million over the last five years.

The veneer of legality around this whole enterprise has always been thin. On the red carpet at the 2008 Hookies, Hurant told an interviewer, "I think the whole outlook towards escorting has changed. People look at this guy and say, 'Oh, he’s an escort. Wow, he’s probably really good in bed.'"

Speaking to Michael Musto in 2012, marketing director Michael Sean Belman, better known as Sean Van Sant, said, "We say the escorts are selling their time only. What happens between you and the escort is up to you. That's the way it's considered legal."

Law enforcement agents refer to these interviews and other statements along those lines at length in their complaint. Despite all the public record information about how the site operates, DHS went to the trouble of sending an agent undercover to the 2015 Hookies to get Hurant's card and ask him how he got started. He purportedly replied, "Have you ever had sex with anyone and it was so good, you had to tell someone? That’s what it’s all about!” Agents and cops also arrested the company's head of sales, its social media coordinator, a sales account manager, and the accountant.

But why now? Why was 18 years the perfect time to take down Rentboy, the direct sales model of which sex columnist Dan Savage argues "put pimps out of business!"

Users of a message board where johns post reviews of escorts from Rentboy—the forum is also mentioned in the complaint—are nervous that the bust could signal the beginning of an effort to go after site users, with one writing, "I for one picked a bad week to give up smoking based on this news."

The human rights group Amnesty International recently came out in support of decriminalizing sex work, with secretary general Salil Shetty saying in a statement, “Sex workers are one of the most marginalized groups in the world who in most instances face constant risk of discrimination, violence and abuse." Journalist Melissa Gira Grant argued now is the time for such sentiment to be tested.

Grant tweeted that Hurant was released from Brooklyn federal court this afternoon on $350,000 bond, and that the other five are also out on bond. A seventh codefendant was arrested out of state. A count of the federal charge the government wants to bring against them carries as many as five years in prison.

In its most recent blog posts and social media postings, Rentboy advertised an essay/video contest to provide college scholarships of $1,500 and a year of free site ads to escorts.

We reached out to the U.S. Attorney's Office and the Department of Homeland Security for insight into why this bust was made now, and what it has to do with the agency's five core missions:

Prevent terrorism and enhancing security;
Secure and manage our borders;
Enforce and administer our immigration laws;
Safeguard and secure cyberspace;
Ensure resilience to disasters

"[Homeland Security] was involved because the crime involved the internet," U.S. Attorney's Office spokeswoman Nellin McIntosh said. "I don’t have an answer as to why now rather than some other time."

We'll update if we hear back from DHS.