For years, the aspiring spy had gone to remarkable lengths to protect his identity and evade detection.
With a cash-bought burner phone, he created an anonymous email account that could send encrypted messages, according to the FBI, then waited to use it.
To avoid suspicion at his job developing America’s most advanced submarines, he allegedly sneaked out sensitive documents for years, a few pages at time.
The Navy veteran’s work for the U.S. government had taught him to spot the clues that betray insider threats, and, according to an FBI affidavit, he would later brag that “we made very sure not to display even a single one.”
But now, after all that caution, the foreign officials Jonathan Toebbe believed he was negotiating with were pushing him to do the one thing he’d been avoiding: come out into the open.
At first, Toebbe - a nuclear engineer and father of two who lives in Annapolis, Md. - pushed back in encrypted email exchanges detailed in the affidavit. “Face to face meetings are very risky for me,” he wrote, “as I am sure you understand.”
A month later, he protested again: “I am sorry to be so stubborn and untrusting, but I cannot agree to go to a location of your choosing.”
He’d already threatened to approach “other possible buyers” if the country wasn’t interested, an FBI agent testified at a court hearing on Wednesday.
Eventually - after a series of trust-building exchanges that involved a secret signal at a Washington, D.C., building and a deposit of $10,000 in cryptocurrency - Toebbe relented.
For almost a decade, Toebbe, who held a top-secret security clearance, had been part of the multibillion-dollar effort to build submarines that could remain submerged and undetected for the longest time possible.
The documents he allegedly smuggled out contained schematic designs for one of the Navy’s most advanced boats - the Virginia-class submarine - with a nuclear reactor that could run for 33 years without refueling.
In this world, stealth was everything. And yet, despite all that technological sophistication, every submarine becomes vulnerable the second it surfaces.
On June 26, Toebbe, 42, drove to West Virginia’s Shenandoah Valley. Accompanying him was his wife, Diana Toebbe, 45, a private-school humanities teacher beloved by students and known among friends for her intelligence and liberal politics. They brought with them a tiny data storage card filled with secrets they allegedly hoped to sell, wrapped in plastic and hidden inside half a peanut butter sandwich.
After years of staying submerged, Toebbe and his wife were surfacing. And unbeknown to them, the FBI was watching their every step.
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When the U.S. government announced the couple’s arrest on espionage charges last week, it filed a 23-page affidavit in support of a criminal complaint. Packed with technical notes, it also contained details as riveting as any spy novel.
There are sly exchanges and red herrings. Traps are set, evaded, then baited again.
But left unanswered in all the plot twists: What drove a suburban engineer and his schoolteacher wife to apparently try to sell secrets to a still-unidentified country?
In many ways, the Toebbes are an unlikely pair to stand accused of such betrayal. Both come from devoted military families.
“We strongly believe in duty and honor,” said Jonathan’s father, Nelson Toebbe, a retired lieutenant colonel in the U.S. Air Force Reserve Medical Service Corps, who declined an interview.
Jonathan’s grandfather served in the Navy during World War II, and his great-grandfather was a veteran of World War I. Jonathan himself served five years on active duty as a Navy nuclear engineering officer and more than two years in the Navy Reserve.
Diana’s family was similarly filled with veterans.
In World War II, her grandfather served on four different submarines in the Pacific, according to relatives and public records. He volunteered for dangerous assignments that tested just how long and deep the boats could stay submerged, relatives said, and passed on his love for submariner culture to his son, Douglas Smay, Diana’s father.
Smay served mostly on surface-level naval vessels instead of submarines, but he created a memorial to honor submariner veterans called “52 Boats,” named for the number of U.S. subs lost in World War II.
As a teenager in Southern California, Jonathan Toebbe was one of the top students at Upland High School.
“When I found out he’d become a nuclear scientist,” said one former classmate, “that didn’t strike me as unusual at all.”
The Upland yearbook devoted an entire article to Jonathan when he was a sophomore, ticking off his involvement in varsity swimming, water polo, the honors program, Eagle Scouts and church.
“When asked what his goals in life were, he replied that ‘one goal in life is to be the best at whatever I do,’ " the article said.
Even as a teenager, Diana had a passion for progressive causes.
For years, she was one of the few White students at her school, riding a bus daily from her affluent suburban neighborhood to attend a magnet program in downtown San Diego that was still struggling with integration.
As a 16-year-old, she lamented the stark inequalities to a local newspaper, pointing out her school’s walkways draped with chain-link fencing. “This looks like a prison,” she said. “Grass - is that so much to ask for?”
It was at Emory University that the couple met and fell in love.
Jonathan, three years younger, was in the graduate program for physics. Diana was in Emory’s PhD program for anthropology.
Among the doctoral students, Diana was known for her desire to challenge the field’s assumptions about gender and race, according to former professors and students.
Drawing on her own struggles with anxiety disorder, she wrote a prizewinning paper about how obsessive-compulsive behaviors were not so different from other ritualized behaviors condoned by society.
She was a study in contradictions. A black belt in martial arts who loved knitting. A staunch feminist who attended Renaissance fairs in the archaic garb of peasant women.
But something about her appealed to Jonathan.
“It was their shared intelligence,” said a relative on Diana’s side of the family.
In her dissertation, Diana began her acknowledgments by thanking her “forever first, my husband Jon, who acted as my midwife during the painful birth of this work.”
They married in 2003, according a marriage certificate from DeKalb County, Ga., and two years later moved to Colorado, where both took jobs as science teachers at the high-priced, private Kent Denver School.
In 2008, Jonathan began pursuing a second advanced degree, in nuclear engineering at the Colorado School of Mines, where a classmate recalled him as easygoing and an avid Dungeons & Dragons player.
But he left the program for the Navy in 2012 after becoming a parent. His professors bemoaned losing him as a potential doctoral student, said the classmate, who now works for the U.S. government and spoke on the condition of anonymity. Jonathan said he needed to make much more than he was getting on a graduate student stipend to support his family.
When they’d first arrived in Colorado, the couple bought a newly built four-bedroom home in Aurora for $268,500. But four years later, Jonathan and Diana were struggling to make payments, according to documents filed by their lender. In August 2010, they were forced to sell the home at a loss, for $206,000.
“The Navy was offering him a job. It was a good deal. Trained nuclear engineers - there aren’t a huge number of us,” said the classmate. “And he was probably one of the smartest guys at the school.”
After moving to the Washington area, Jonathan specialized in nuclear power and was eventually assigned to the Naval Nuclear Propulsion Program, which oversees the nuclear reactors used to power more than 60 aircraft carriers and submarines in the naval fleet. He was never deployed by the Navy, nor did he serve on any ships, according to service records and court documents. Toebbe ended his active-duty service in 2017 but remained in the Navy Reserve until 2019. He was earning $153,737 a year for his work as a nuclear engineer, according to a defense official.
Meanwhile, Diana taught at the Key School in Annapolis, where tuition runs as high as $31,050 a year. She was a meticulous instructor who pushed students to think differently, said former students and their parents.
The couple bought a modest house for $430,000 in 2014 in the Annapolis neighborhood of Hillsmere Shores, where residents have a private marina with direct access to a river and a beach. Their two kids, now 11 and 15, went to Diana’s private school, which allows each faculty member to enroll one child tuition-free.
“They had money. They both worked hard. It’s not like they were having difficulty with the bills,” said a relative of Diana’s.
On Facebook and Instagram, Diana chronicled their life together - a look at a potato casserole she baked, pictures from a beach vacation, and a video of her children playing in costumes. She posted knitting tutorials on YouTube, coaching her viewers with generous dollops of encouragement.
“If you’ve gotten this far, well done. I’m really, really proud of you,” she tells first-time knitters in one video. “Take a second and give yourself a pat on the back.”
Her husband kept a lower profile online.
His Facebook page lists “Cryptonomicon” as one of his favorite books.
It’s a science-fiction novel that runs nearly 1,000 pages and spans three generations. The book begins with a young Navy captain in World War II and eventually chronicles his hacker grandson’s mission to build a place where encrypted data can be exchanged without scrutiny.
The key to keeping that data haven running, it turns out, is a sunken Nazi submarine.
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Jonathan Toebbe’s own saga began on April 1, 2020, with a brown envelope with four U.S. postage stamps, according to the affidavit.
Toebbe allegedly sent the package anonymously, with a return address in Pittsburgh, to an unidentified foreign government. Inside were sensitive U.S. Navy documents and instructions on how the country - believed by many national security experts to be a U.S. ally - should reply using an encrypted email service.
For almost nine months, the receiving country held on to the package before it apparently handed it over to the FBI on Dec. 20, 2020.
Six days later, an FBI agent - posing as a foreign spy handler - reached out to Toebbe at the anonymous email address he provided.
Toebbe was cautious at first. In his reply, he avoided any details that might give away his identity, simply calling himself “Alice,” a common placeholder name in cryptographic circles.
When the supposed foreign official asked him to meet face-to-face with a “trusted friend” - someone with a “gift . . . to compensate for your efforts” - Toebbe knew better.
“I am uncomfortable with this arrangement,” Jonathan wrote on March 5, 2021, according to the affidavit. “I propose exchanging gifts electronically, for mutual safety.”
He asked his new friend for $100,000 in Monero, a cryptocurrency popular with cybercriminals that conceals the sender, receiver and even the amount exchanged.
“I understand this is a large request,” he said. “However, please remember I am risking my life for your benefit and I have taken the first step. Please help me trust you fully.”
In the five months that followed, Toebbe and his handler engaged in delicate negotiations. His emails adopted a vulnerable tone that laid bare his dilemma: his need to remain hidden was pitted against worries of offending his new friends or losing their interest.
The handler suggested using a neutral location as a place for dead drops: “When you visit the location alone, you retrieve a gift and leave behind the sample we request.”
But Toebbe did not want the foreign government picking the location.
“I am concerned that using a dead drop location your friend prepares makes me very vulnerable,” he wrote. “If other interested parties are observing from the location, I will be unable to detect them. . . . I am also concerned that a physical gift would be very difficult to explain if I am questioned.”
But the handler kept insisting that the foreign government select the dead drop’s location. And Toebbe kept resisting.
“I must consider the possibility that I am communicating with an adversary who has intercepted my first message and is attempting to expose me,” he said. “Would not such an adversary wish me to go to a place of his choosing, knowing that an amateur will be unlikely to detect his surveillance?”
So, Toebbe proposed that his handlers fly a “signal flag” atop a building their country controlled in Washington over Memorial Day weekend - to prove they were who they claimed.
Yes, that can be arranged, his handler replied.
On Monday, May 31 - after the FBI coordinated with the country to put the signal in place - Toebbe wrote back elated. He’d seen the signal and was finally willing to surface.
“Now I am comfortable telling you,” he said. “I am located near Baltimore, Maryland. Please let me know when you are ready to proceed with our first exchange.”
On June 26, at 10:41 a.m., Jonathan and Diana appeared at the appointed location in Jefferson County, W.Va. Earlier that month, according to the affidavit, Toebbe had been sent $10,000 in Monero cryptocurrency.
FBI agents watching the site described Diana standing three feet from her husband, working as his apparent lookout as he placed into the dead drop the peanut butter sandwich they’d brought containing a 16-gigabyte SD memory card.
On the card, the FBI said, were details on the nuclear reactor used on one of the Navy’s most advanced U.S. submarines - a $3 billion ghost in the water, capable of launching cruise missiles from behind enemy lines.
Over the next four months, the FBI agent posing as a spy handler arranged for three more dead drops - an SD card hidden inside a sealed Band-Aid wrapper in Pennsylvania, another concealed in a chewing gum wrapper in eastern Virginia.
With each successful drop, Jonathan’s emails grew more effusive.
“You can not [imagine] my relief at finding your letter just where you told me to look!” he wrote in one.
Asked if he was working alone, Jonathan responded, in what the FBI said was an apparent reference to Diana: “There is only one other person I know is aware of our special relationship, and I trust that person absolutely.”
He dangled the possibility of more than 11,000 pages of sensitive documents to follow. For a price of $5 million in cryptocurrency, he said, he would deliver it all.
But, he added, he was aware of the risks.
“I have considered the possible need to leave on short notice,” he wrote. “Should that ever become necessary, I will be forever grateful for your help extracting me and my family...I pray such a drastic plan will never be needed. . . .”
He’d also discussed with his wife, at some point, the possibility of fleeing the country, according to court testimony Wednesday. Using the phone app Signal, the couple sent encrypted messages:
“We have passports and savings,” Jonathan wrote. “In a real pinch we can leave quickly.”
“Let’s go sooner rather than later,” Diana replied.
“I really don’t want to go back to making $50,000 a year, especially in a country I don’t know the language,” Jonathan responded.
“I don’t see how the two of us wouldn’t be welcome,” she said.
On Saturday, Oct. 9, those plans fell apart.
While in West Virginia making their fourth and final drop, Jonathan and Diana finally came face to face with the handlers he had been working with all along: agents from the FBI, who promptly arrested them.
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On Wednesday, Jonathan and Diana entered a federal courtroom in West Virginia with shackles around their wrists and ankles.
In separate bail hearings, Jonathan did not contest remaining in jail until trial. But Diana’s lawyer argued for her release.
She wore an orange jumpsuit emblazoned with the word INMATE and brown sandals. She kept her eyes mostly fixed on the judge and the FBI agent testifying against her.
Her lawyer asked the judge to consider the couple’s two children, maintaining that they need their mother.
In response, the prosecutor noted that during the final dead drop earlier this month, the couple left their youngest child home alone in Maryland.
Jonathan didn’t bring his phone and Diana turned hers to “airplane mode” in an apparent attempt to avoid being tracked, the prosecutor said.
If Diana was so concerned about the children, the prosecutor demanded, why did Diana and Jonathan leave an 11-year-old with no way to contact them?
Authorities found the child alone when they searched the Toebbe’s house the day of their arrest. But they also found in the couple’s bedroom items suggesting the family was prepared to flee: $11,300 in cash - $100 bills wrapped by rubber bands. Their children’ passports. A ready-to-go backpack with a computer and latex gloves. And a crypto wallet - a device used to store and maintain cryptocurrency transactions.
The Toebbes have been charged with conspiracy and communication of sensitive government records to a foreign nation. If convicted, they could face life in prison. Wednesday’s hearing ended with the judge saying he needed more time to decide whether Diana should be released while she and Jonathan fight their case.
In the meantime, their lives have imploded.
On Diana’s Instagram, photos of her children have been overrun by strangers posting expletive-laden condemnations of the entire family.
“Say goodbye to the kids forever,” reads one with a laughing emoji.
“Hanging, firing squad, electric chair. . .??”
Jonathan’s cousin, Mark Slaughter, said those who know the Toebbes are struggling to reconcile the couple charged with espionage with the couple they once admired.
“People in the family are having a hard time processing it,” said Slaughter, who has served as a Marine sergeant and Army captain. “There’s nothing here that makes sense.”
Both sides are now deliberating which relative could take them in if Jonathan and Diana are imprisoned for years or life, another relative said.
“I worry whether the kids will ever be able to heal or move on from this,” said one relative. “Imagine what it’ll be like for them to grow up with that Toebbe name hanging over them. No matter what their parents may or may not have done, those children are innocent.”
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The Washington Post’s Devlin Barrett, Alice Crites, Alex Horton, and Moriah Balingit contributed to this report.