Kingpin 2.0?

“I remember—it must’ve been in March 2006 when we were a few weeks before the trial—I was talking to someone at [the Justice Department] in D.C.,” former assistant U.S. attorney Elizabeth Peterson recalls. “I told him we had ultimately charged [Smith] under the kingpin statute. He said, ‘Wait, what drugs are you dealing with?’ I said, ‘Well, Vicodin was his bestseller.’ The individual said, ‘He wasn’t even selling Oxycontin? You guys are crazy to think you’re gonna get a kingpin charge on someone who wasn’t dealing with Oxycontin.’ ” Her colleague’s skepticism only strengthened Peterson’s resolve—she believed Vicodin to be a dangerous drug, regardless of its inferior legal status. “I became all the more convinced we were doing the right thing and that we would ultimately prevail,” she says.

Smith’s parents hired Joe Friedberg, one of the best local defense lawyers money could buy, but the government’s mountain of evidence against Chris and codefendants Liebermann, Adkins, and Griepp would prove insurmountable, although the fed’s case had its challenges—not the least of which was explaining to the jury the meaning of common cyberspeak such as LOL (“laugh out loud”) and ROFLMFAO (“rolling on the floor, laughing my fucking ass off”). The company e-mails and instant messages were written in the snarky, blithely derisive tone endemic to the medium: “These $599 packages are popular,” Smith wrote. “Fucking addicts. LOL.” Beyond that, it was a matter of showing slides of Smith’s fabulous cars, showcasing testimony about how he cheated on his wife, and interviewing customers who had ordered Vicodin via his online operation.

Smith’s only chance lay in the language of the law. In order to convict him under the kingpin statute, the jury had to believe he was “acting as a drug dealer and trafficker as conventionally understood.” Friedberg forbade Smith from wearing a suit and tie to court, having him show up in the same tech-geek ensemble he wore to work. And he argued that the online model—with only virtual contact connecting doctor, “patient,” and pharmacy—was quite different from the model you would find, say, on a North Minneapolis street corner. But the prosecution portrayed Smith as a kid swimming in cash, who was paranoid to the point of training cameras on his employees and making them walk through metal detectors, who had a sexy wife and a stripper girlfriend who was shuttled around by a bodyguard whose fingerless gloves were wrapped around the wheel of a $300,000 automobile.

After a six-week trial, the jury awarded the state its unprecedented conviction—the first of its kind against a nondoctor and nonpharmacist in an online pharmacy case, according to Peterson—and Judge Davis sentenced Smith to thirty years in prison.

“I failed him,” says Friedberg, who rarely loses. “We needed a plain reading of the law, and we didn’t get the jury instruction I needed.” But the lawyer says he’s most disappointed that he couldn’t persuade his client to cooperate with the government. He shakes his head. “If I could have controlled this kid’s conduct and if he really would have worked with me as I thought he was going to in negotiating with the government, he’d probably be getting ready to get out.” Instead, says Friedberg, Smith refused to cooperate, obfuscating and lying outright in a proffer hearing with the FBI. “The idea that he didn’t do anything wrong is ridiculous,” says Friedberg.

When I ask him what he said to talk some sense into Smith, he stares at me. “What I told him is privileged, but what do you think?” he says. “No rules apply to Chris. That’s how he was brought up. And Chris Smith is just not as smart as he thinks he is. He’s clever, but he thinks he understands the legal subtleties and he really doesn’t.”

At one point, the government agreed to a five-year prison deal, according to Friedberg, but Smith’s conduct between his arrest and his conviction doomed him to the thirty-year term. From his arrest in June 2005 to his sentencing in 2007, Smith tormented the staffs of three separate holding facilities—attempting everything from sneaking a computer into a halfway house to sneaking Xanax into the Sherburne County jail.

Perhaps the most egregious example of Smith’s self-destructiveness and a reminder of his computer genius is the way Smith used a new Internet technology to bypass the security systems at Sherburne County and send data over the phone to do business. According to Kyrilis, Smith had another inmate go through the yellow pages to find a disconnected law office number. “By the time he found one that would work,” Kyrilis says, “he got all the way to the Ks.” Smith then used his lawyers to get the number to a contact in the Philippines, Roanna Cleofe, who registered the 612 number with Integra, an Internet company that specializes in voiceover Internet protocol, which allows voice and data to travel over the same network. “She would just answer, ‘Law office,’ and then forward his calls anywhere he wanted.”

According to Kyrilis, no one monitored the first forty or so calls, but when someone at the Sherburne County jail finally did, Smith was recorded talking to Cleofe about plans to murder a federal witness. One of the recordings was introduced at Smith’s trial; it begins with Chris complaining about Anita’s attitude, then crescendos into talk about violent action against the family of Bernadette Hollis, the so-called “Spam Queen” of Kansas City and one of the government’s key witnesses.

Chris Smith: When we get a little closer to trial, you know, I think we’re gonna have to hire a private detective to get pictures of Berni’s kids. And we can do a little bit of e-mailing and electronic influence about a week before trial.

Roanna Cleofe: About what?

CS: Just let her know that, you know, if she wants to talk on the stand, that’s perfectly fine, but we’re also going to give her the option of picking which one of her kids she’s going to sacrifice for doing so.

RC: Are you sure?

CS: What, you think I’m joking?

RC: That’s scary.

CS: So is going to prison for twenty years.

RC: [Sighs.]

CS: This is a kill-or-be-killed world. One of my lawyers wanted to have her taken out altogether. [Laughs.] I mean you know what kind of services I’m looking for, right?

RC: Yes, yes.

CS: Alright.

RC: ’Cause I know [my uncle] knows someone from China and I’m not sure if—and Russia—I’m not sure if, you know—

CS: I mean I’m looking for like a full service.

RC: Yeah.

CS: There was a famous comment by Joseph Stalin, the most powerful man of the whole world. You want to know what it was?

RC: What?

CS: “No man, no problem.”

RC: [Laughs.] OK.

CS: I’m really not joking. I got to get out of here.

RC: I know.

CS: I got to get out of here. That’s the only way I can do it.