How This Freelance Hostage Negotiator Talked to ISIS Leaders and Enraged the FBI

The War on Terror claims a Delaware car salesman, jailed for appointing himself a hostage negotiator with ISIS

Toby Juan Lopez
Toby Juan Lopez Courtesy of Toby Juan Lopez's family.

UPDATE: Toby Juan Lopez was set free on on bail on March 24, 2016.

What does the FBI have to fear from a car salesman from Delaware with a Walter Mitty streak?

Evidently a lot, judging from the fact that the salesman—44-year-old Toby Juan Lopez—has been kept in a series of federal prisons over the past year for allegedly threatening an FBI agent. Lopez says he was merely venting frustration because the agent refused to act on information he obtained that he believed might help free American hostages held by the Islamic State in Syria. The government sees it otherwise.

Lopez’s extended incarceration, based on a scant, four-page criminal complaint, is a tale of one man’s inflated sense of involvement in the fight against terrorism—and also a story of the government’s intolerance of anyone meddling in its business.

In August 2014, the Toyota salesman from Dover, Del., called me out of the blue; he found me through a web search looking for a publicist to help pitch his “blockbuster” to the media. It was hard not to be intrigued by this affable stranger with a cloak-and-dagger tale.

Describing himself as a patriot who counted several military friends killed in Afghanistan, Lopez was incensed by the brazen beheading of journalist James Foley and other barbaric murders by the Islamic State. As a new breed of jihadists took to social media to flaunt their sadism, Lopez used his Twitter account to scold and challenge those affiliated with the Islamic State, questioning their fealty to the Quran.

A self-described Chechen rebel who bragged about his exploits in the Middle East relished debating Lopez and invited Lopez to join him in a discussion over email and then real-time audio conversations through encrypted corners of the web.

Lopez was convinced his correspondent was who he said he was—Abu Omar al-Shishani, the nom de guerre of Tarkhan Tayumurazovich Batirashvili, former sergeant in the Georgian army who underwent training by U.S. Special Forces and later joined the Islamic State as a commander in Syria and Iraq and “warden” of prisons holding Western hostages.

He happened to be one the most wanted fugitives in the word.

Over several months, starting in the summer and continuing until December 2014, Lopez and al-Shishani had discussions about everything from Sharia law, military strategy and American foreign policy to how the ISIS warrior could obtain a pink iPhone for his daughter. On several occasions, al-Shishani sent Lopez a few seconds of video, revealing the likeness of a camouflaged fighter with a long red beard and skullcap speaking from a tent. If it was a hoax, it was an elaborately staged one.

Lopez played me multiple snippets of their Skype calls—he had accumulated more than 20 hours of recordings with al-Shishani, whom Lopez referred to as “Sheik Omar.” The basso voice sounded Russian, holding forth on infidels and troops in heavily broken English. Lopez said he had compared his audio cache to several other available recordings of al-Shishani and that he had no doubt that they were one in the same.

As attention to the Islamic State increased, the sheik complained that Syria was being overrun with ragtag mujahideen wanabees from every corner of the Muslim world, most of whom needed considerable babysitting. Squabbling among senior ranks of the Islamic State and U.S. drone strikes made him wary of remaining in Syria and he talked about returning home to fight the Russians. But he also sought help from Lopez to secure cash that might be used to ransom American hostages held by the Islamic State.

Certain he was sitting on a rich lode of intelligence, Lopez contacted the Baltimore office of the FBI’s Joint Terrorism Task Force (JTTF) to share his recordings, which he carefully annotated. According to Lopez, agents listened with interest and, without expressly saying so, did nothing to indicate that Lopez was not communicating with the real al-Shishani.

Up to this point, Lopez had been a model citizen in the international dragnet for terrorists—he saw something and said something. This was an ordinary citizen who had stumbled into direct contact with America’s gravest enemy and alerted the government in a quest to save lives.

Unfortunately, he continued to say something—in fact, too many somethings. Perhaps it was because his channels with al-Shishani went dark in late 2014—there were reports that the ISIS commander had been killed, but also Lopez was reluctant to follow through on plans to deliver funds to al-Shishani’s contacts in Sweden.

That the Islamic State military leader may have been luring Lopez to serve as a courier to hand-off payments with European operatives made several journalists who looked into his story question whether the man from Delaware was being scammed, and if Sheik Omar may have in fact been a fraud (several reporters spent the better part of a day in Delaware reviewing Lopez’s recordings and were fairly convinced they were the real deal, but impossible to verify without forensic analysis).

Sheik Omar
Abu Omar al-Shishani. Photo YouTube screen grab.

In any case, Lopez began pestering the FBI with unwanted advice on how to negotiate with al-Shishani and his posse. He also felt the FBI was not taking his offer to help seriously, based on information he gleaned from months of discussions with an apparent ISIS leader, including intelligence regarding Kayla Mueller, a young aid worker from Arizona whom al-Shishani had referenced in their conversations.

Over a nine-day period last February, the JTTF agent who had previously listened to Lopez’s recordings stated in the criminal complaint that he was barraged with some 80 emails from him. According to an affidavit by another FBI agent referenced in the complaint, those messages “generally expressed concern that [Lopez] was not being supported by the FBI in his self-perceived efforts to negotiate a release of ISIL hostages. One of the emails…stated in part, ‘All I have to do is say go!!!…You understand correct??? Any attempt to arrest me will be treated as a hostile act…’ ”


Clearly, Lopez believed his own action-hero persona. When Mueller was reportedly killed in a Jordanian-led airstrike in Al-Raqqa, Syria, around February 6, 2015, an irate Lopez complained that the FBI had botched an opportunity for working his purported Islamic State contacts to secure the hostage’s freedom. On February 11, 2015, in a fit of righteous anger, he tapped out another message to the JTTF agent: “Just remember whatever ends up happening to you…You deserved it, you lying piece of shit!!”

Kayla Mueller
Kayla Mueller. YouTube Screen Grab

The FBI had seen and heard enough. Construing his email as a credible threat to one of its own, the bureau dispatched a caravan of agents to Lopez’s mother’s house in Dover to arrest him. “He knew they were coming for him,” his mother Joyce Lopez later told the Observer. “Toby would never hurt a fly, but he was just so upset that they were ignoring what he knew to try and help that poor girl.”

It’s understandable that the FBI wanted to silence the freelance interloper with no credentials who inserted himself into active foreign terrorist investigations and possible military matters. It didn’t help that Lopez supposedly continued to tweet other ISIS members regarding hostage negotiations, or that he was reaching out to family members of several murdered hostages—even if such activity constituted protected speech, it brought him too close to the FBI’s no-fly zone.

However, instead of trying to strike a plea deal to keep Lopez from further contact with its agents or the families of hostages, the government has incarcerated him for more than a year, shuttling him from facilities in Oklahoma, Philadelphia, Delaware and New York City. His longest stint was in the Federal Correction Complex in Butner, N.C., famous for housing Bernard Madoff and Jonathan Jay Pollard. Lopez was kept for months in a medical unit at Butner—reflecting the government’s assertion that his invented role as a hostage negotiator stemmed from a mental disorder. Whether Lopez deserves to be behind bars rather than receiving treatment from physicians deserves debate.

The U.S. Attorney’s office in Delaware did not respond to requests for comment about the case.

BUTNER, NC - NOVEMBER 20: The federal prison in Butner, North Carolina where Convicted Israel spy Jonathan Pollard was released from is seen on November 20, 2015 in Butner, North Carolina. Pollard, 61, spent 30 years in prison after being caught selling American intelligence secrets to Israel. The prison camp houses three levels of security on the multi-building Federal Correctional Institute campus.
BUTNER, NC – One of the federal prisons, where Toby Juan Lopez was held. (Photo by Sara D. Davis/Getty Images)

Is Toby Lopez a national security threat or potentially violent? According to his family, he has no prior arrest record and no history of harboring radical beliefs. There seems little doubt that his fevered communication with the FBI—irritating as it might have become—was motivated by a sense of personal duty to help, not hinder, the freeing of American hostages. Even in his serial conversations with al-Shishani, Lopez says he was never sympathetic to the ISIS agenda and only sought to prevent further harm to those in captivity.

But Lopez’s case raises important questions regarding citizen engagement in an age of terror watchfulness.

‘I would characterize Lopez as a gadfly attorney general who was upset with the government for not being responsive to the evidence he’d gamely gathered at his own risk and tried to present. You can question his tactics and call him a pain in the ass, but you shouldn’t be arresting him.’—Ron Kuby

No doubt many Americans with all sorts of beliefs have been able to strike up their own direct contact with the Islamic State in the past several years. The government is right to want to choke off that dialogue, especially in the wake of homegrown terrorism such as the shootings last December in San Bernardino.

Lopez, however, was no jihadist recruit. There is nothing to suggest he was caught plotting or advocating violent attacks based on the urgings of some infidel-cursing imam. He naively thought he could reform Sheik Omar and others he communicated with, and that his intel could be used to aid the Joint Terrorism Task Forces. “I knew the correct way to communicate with these people, to gain their trust and make headway in freeing Americans—that was my No. 1 goal,” he told me on several occasions. However, in acting out with his flood of angry emails, he crossed the line from nuisance to menace, at least in the eyes of the FBI.

The question remains: Is Lopez delusional or otherwise mentally unstable? There is his continuing fixation with al-Shishani, and his unshakable certainty that he had a direct line of contact to the the Islamic State’s inner circle. There is also his incessant badgering of the FBI even after being told to stand down—could that have been a sign of someone about to snap?

In its complaint filed last February, the government plays up Lopez’s agitation and presents one additional ominous element: “On February 10, 2015, someone who introduced herself as being the defendant’s mother walked into Delaware State Police Troop 3 in Kent County, Del., and informed law enforcement officers therein that the defendant had purchased a firearm. She indicated that she was concerned about her son having a weapon because he was in a poor mental state.”

That sounds damning. However, Lopez’s mother Joyce denies she ever claimed her son was mentally disturbed or posed a danger to law enforcement, only that he was fearful that the long hand of the Islamic State could reach out to him for exposing his contacts and allowing the JTTF to bungle its dealings over Mueller, leaving other hostages vulnerable and himself at risk of retribution. She also says the FBI special agent later phoned her during a drive to Butner, essentially confirming that Lopez’s communication with al-Shishani had been authentic. In further conversations with Lopez’s father, half-brother and sister-in-law, all of them describe an individual of high intelligence and intense convictions; they are uniform in their assessment that Lopez never exhibited anything resembling mental illness.

Thus, an uncertainty remains. Was Lopez’s paranoia the result of fantasy and a possible break from reality? Or, if his contacts were genuine (including other higher-ups in ISIS), might he have had reason to think he could be a target for sharing what he knew with government agents?

According to court records, Mr. Lopez was found incompetent and subject to involuntary medication. His public defender recently filed an unopposed motion for a continuance, allowing him 45 days to receive an independent evaluation by a mental health expert.  He will have his next hearing on April 5th.

Several criminal defense lawyers consulted by the Observer say that under a determination of mental incompetence, Lopez can indeed be detained indefinitely. New York attorney Gordon Mehler, who served as a deputy assistant attorney general in the Clinton administration and also domestic terrorism coordinator for New York’s Eastern District, explains that such a finding by a government psychiatrist could trump normal time limits for pre-trial incarceration. Mr. Mehler notes that the Federal Criminal Code permits the government to hold Lopez until such time as his competency is resolved. He adds that some courts allow for forced medication of a defendant to obtain the level of competency in order to proceed to trial, even though that is subject to argument.

“The switch here is that it is typically the defense that will be seeking to demonstrate incompetency as part of a possible insanity defense,” Mr. Mehler says. “In this instance, the defendant wants to prove that he is sane so that he can have his day in court and show his innocence.”

Another former prosecutor tells me he’s handled similar cases to Lopez’s, but given the filings required, plus the request for an independent psychiatric evaluation and repeated travel to Delaware, he would need $75,000 to facilitate Lopez’s release. I’ve looked into whether some law firms we work with on press relations might represent Lopez pro bono, but his case doesn’t rise to the level of wrongful conviction that attracts most firms to individual criminal matters. And I have yet to find an advocacy group specializing in Islamic State-fueled vigilantism. And so, he sits in prison.

Ron Kuby, one of New York’s best-known defense attorneys and civil rights advocates who has represented several alleged jihadists, offers his own experienced view as to what’s kept Lopez marinating in jail for so long.

“It sounds like the FBI was sick of hearing from this guy and so they decided to shut him up by arresting him for a nonexistent threat,” Mr. Kuby says after reviewing portions of the Lopez complaint. “You can certainly question the wisdom of a private citizen imposing himself into ISIS hostage negotiations, and there are statutes in place prohibiting people from conducting business with foreign governments on matters of state. But that is not the case here. I would characterize Lopez as a gadfly attorney general who was upset with the government for not being responsive to the evidence he’d gamely gathered at his own risk and tried to present. You can question his tactics and call him a pain in the ass, but you shouldn’t be arresting him.”

Regarding the specific charges in the criminal complaint, Mr. Kuby dismisses them as “ridiculous,” particularly Lopez’s email warning the FBI special agent that he deserved whatever happens to him. It is on the basis of that message that the government concluded that Lopez had hostile intent and constituted a threat.

“That’s not a threat—it’s an insult,” Mr. Kuby argues. “More accurately, it’s a perception of karmic events that also happens to be demonstrably untrue by any empirical standard. Call it a philosophical mindset or even a wish, but it’s certainly not a legally actionable threat.”


Every week or two the telltale call comes in on my cellphone from an “Unknown Number.” It begins with a recorded operator’s voice alerting me, “You have a prepaid call from an inmate at a federal facility. Press ‘five’ to accept or simply hang up if you wish to decline.” Sometimes I’m in a meeting or on another call, or just walking the dog or having dinner—and so let the interruption pass unanswered. But then I immediately feel guilty and make sure to take the next one. And after a few seconds’ pause, Lopez comes on.

For someone who’s been in federal jail for more than a year, he remains remarkably upbeat.

“Hey, buddy, what’s going on?” he always asks, hopeful for fresh news. He tells me he hasn’t spoken to his lawyer in months and has little clue about his future. He spends his time in the law library at his current location (most recently Manhattan Correctional Center) and now recites statutes under which he feels he should be sprung. That includes certain provisions of the federal rules of criminal procedure regarding terms for bail or his right to force a competency hearing. He’s also become conversant with First Amendment privilege.

As it happens, his pen pal al-Shishani was reported by Russian media to have been captured in Iraq by U.S. special forces this past December. No confirmation has been forthcoming from the Pentagon, but it’s ironic to think that both one of the FBI’s most wanted men and its least wanted are now likely prisoners from very different parts of the same war.

I ask Lopez if he would consider promising to cease all further communication with jihadists and the FBI to expedite his release. He assures me he would, but under one condition: “Just don’t let the JTTF tell me I didn’t know what I said I know,” he says. “They know it, and I know it.”

Allan Ripp runs a press relations firm in New York. How This Freelance Hostage Negotiator Talked to ISIS Leaders and Enraged the FBI