The Toebbes: a Modern Spy Story


Kit Reviewer
Book Reviewer
This is a really interesting story:

The accused spy knew stealth was crucial from his work on submarines. He surfaced anyway.​

Jonathan Toebbe and Diana Toebbe, after their arrest on espionage charges. (AFP /West Virginia Regional Jail and Correctional Facility Authority)
By William Wan
Ian Shapira

Today at 7:00 a.m. EDT

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 snuck sensitive documents out 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.”
Get caught up quickly. Subscribe to the day’s top stories, via SMS.
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.”
But 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, 42, who held a top-secret security clearance, was 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.

Navy engineer and his wife charged with trying to sell submarine secrets with a foreign country

U.S. Navy nuclear engineer Jonathan Toebbe and his wife have been charged for trying to sell nuclear submarine secrets to a foreign country in December of 2020. (Reuters)
On June 26, Toebbe 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, wrapped in plastic and hidden inside half of a peanut butter sandwich, filled with secrets that they allegedly hoped to sell.

After years of staying submerged, Toebbe and his wife were surfacing. And unbeknownst to them, the FBI was watching their every step.

‘Duty and honor’​

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.
Navy nuclear engineer and his wife charged with trying to share submarine secrets with a foreign country
There are sly exchanges, red herrings and misdirection. Traps are set, evaded, then baited again.

Left unanswered in all the plot twists: What drove a suburban engineer and his schoolteacher wife to try to sell secrets to a still-unidentified country.
In many ways, the Toebbes were an unlikely pair to stand accused of turning against America. Both came 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.
In addition to Jonathan’s father, his grandfather served in the Navy during World War II, and his great-grandfather was a veteran of World War I. And 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 C. 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 submarines lost in World War II.

Diana Toebbe’s father, Douglas C. Smay, created the “52 Boats” memorial in San Diego, a portion of which is seen above, so named because it commemorates 52 submarines the United States lost during World War II and the crews that served aboard them. (John Gibbins/San Diego Union-Tribune/ZUMA Press)
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, one of several people who spoke about the Toebbes on the condition of anonymity to speak freely about their recollections. “that didn’t strike me as unusual at all.”

The Upland yearbook devoted an entire article to Jonathan during his sophomore year, 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 still struggling with integration.

As a 16-year-old, she lamented to a local newspaper the stark inequalities in funding and pointed 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 anthropology doctoral students — all crammed into the department’s tiny basement office — Diana was known for her desire to challenge the field’s assumptions about gender and race, according to several former professors and students.

Drawing on her own struggles with anxiety disorder, she wrote a prize-winning paper about how obsessive-compulsive behaviors were not so different than 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 well-regarded 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 potential doctorate student, said the classmate, who now works in the federal government and spoke on the condition of anonymity. But Jonathan said he had a family to support and needed to make much more than he was getting on a graduate student stipend.

When they first arrived in Colorado, the couple bought a four-bedroom newly built 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 against them. 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, for the next nine years, 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 2020.

The home of Jonathan and Diana Toebbe, in the Annapolis neighborhood of Hillsmere Shores. (Brian Witte/AP)
Meanwhile, Diana taught at the Key School in Annapolis, where tuition runs as high as $31,050 a year. She was a meticulous teacher who pushed students to think differently, said former students and their parents. But she was also warm and encouraging, becoming a mentor to many girls.
The couple bought a modest house for $430,000 in 2014 in Annapolis’ Hillsmere Shores, where residents have their own private marina with direct access to a river and a beach. Their two kids went to Diana’s private school, which allows children of faculty members to attend tuition-free.
“They had money. They both worked hard. It’s not like they were having difficulty with the bills,” said a close relative of Diana’s.
On Facebook and Instagram, Diana chronicled their life together — photos of a potato casserole she baked, 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 halfway through one of the videos. “You should 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 moves in time to the present day, when his grandson, a hacker, embarks on a 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.



Kit Reviewer
Book Reviewer
Part 2

Risking my life’​

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, D.C., 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 away 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.
Encoded 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.

The Virginia-class attack submarine USS Texas returns to Joint Base Pearl Harbor-Hickam after a 2010 deployment. The Virginia-class of submarines is the focus of documents that Jonathan Toebbe is accused of smuggling out. (MC2 Ronald Gutridge/U.S. Navy )
Over the next four months, the FBI agent posing as spy handler arranged for three more dead drops. At the bureau’s instruction, Jonathan and Diana drove to Pennsylvania in July with an SD card hidden inside a sealed Band-Aid wrapper. In August, Jonathan traveled alone to Eastern Virginia and deposited an SD card concealed in a chewing gum packet.
With each successful drop, Jonathan’s emails grew more relaxed and effusive.
“You can not [imagine] my relief at finding your letter just where you told me to look!” he wrote in one.
“One day, when it is safe, perhaps two old friends will have a chance to stumble into each other at a cafe, share a bottle of wine and laugh over stories of their shared exploits,” read another.
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. … We have passports and cash set aside for this purpose. I pray such a drastic plan will never be needed. ...”
On Saturday, Oct. 9, those fears were realized.
While making their fourth and final drop in West Virginia — a year-and-a-half after he first contacted the foreign country — Jonathan and Diana finally came face to face with handlers they had been working with all along: Agents from the FBI, who promptly arrested them.

‘Not the person I know’​

The Toebbes have now been charged with conspiracy and communication of sensitive government records to a foreign nation. If convicted, they could face life in prison.
At a hearing scheduled for Wednesday in federal court, a judge will determine whether to continue detaining them.
The nuclear submarines Jonathan worked on are built to carry deadly payloads. Some are armed with tomahawk missiles, others with nuclear warheads capable of leveling entire cities.
Now, in the wake of the couple’s arrest, 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.
“Your name will be added to the list of American Traitors: aldrich ames, robert [Hanssen] ...”
“Hanging, firing squad, electric chair…??”

Those who know Jonathan and Diana are struggling to reconcile the couple in the affidavit with the couple they once admired.
“This is not the person I knew. The warm, funny, crazy smart woman who cared and stuck up for other people,” said one friend who’s known Diana for more than a decade.
She refused to speak by name, like dozens of other friends, co-workers, former teachers and students contacted for this story, who fear being associated with accused spies.
The greatest bewilderment was voiced by relatives, who are worried not only about Jonathan and Diana but also the fate of their two children.
“People in the family are having a hard time processing it,” said Jonathan’s cousin, Mark Slaughter, who has served as a Marine sergeant and Army captain. “There’s nothing here that makes sense.”
Both sides are trying to figure out how best to care for the children, deliberating which relative could take them in if Jonathan and Diana are imprisoned for years.
“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.”
Alice Crites, Alex Horton, and Moriah Balingit contributed to this report.


It was Papua New Guinea. They have a big submarine force program under way.
What do you mean, you never heard that? Of course you didn't - its secret...
I thought she looked quite "MILFY do-able" in a Don't t. e. Pikey way ...just.
And then.....not so much.
Lock 'er up.


Comments on another page suggest that South Korea or Taiwan wanted the sub plans.

Both have very strong technical resources, and feel threatened by North Korea and China .


I thought she looked quite "MILFY do-able" in a Don't t. e. Pikey way ...just.
And then.....not so much.
Lock 'er up.
Looking at the picture Iwas in two minds as to whether it was a bloke! (Not sure what that says about you...) :oops:
Life, no parole, solitary.

The Septics don't take well to this kind of treachery.
I hope they get the Electric Chair
But their home in Maryland has a BLM poster......

...water-board them first, THEN sit them on Old Sparky....
Wonder which country grassed on them? India,France, Luxembourg?
Can't see it being the usual suspects.
If must be the Australians, as they're the ones in the market for new nuclear subs.

More seriously, given the assumption that the country approached as a buyer was supposedly a US ally,
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.

it would almost certainly have to be one who already builds submarines or might build them otherwise there would be no point to approaching them. That's a pretty short list of potential customers.
If must be the Australians, as they're the ones in the market for new nuclear subs.

More seriously, given the assumption that the country approached as a buyer was supposedly a US ally,

it would almost certainly have to be one who already builds submarines or might build them otherwise there would be no point to approaching them. That's a pretty short list of potential customers.
Well the Israeli's have got previous for this sort of thing and they have got Nukes, but I can't see the need for Hunter-Killers or Bombers in the Med.
If must be the Australians, as they're the ones in the market for new nuclear subs.

More seriously, given the assumption that the country approached as a buyer was supposedly a US ally,

it would almost certainly have to be one who already builds submarines or might build them otherwise there would be no point to approaching them. That's a pretty short list of potential customers.
The Red Sea Pedestrians.