The Death of a Fake Pentagon Analyst

In part two of our look into the bizarre circumstances surrounding the death of Latvian born Russian-American businessman Dan Rapoport, we expose his alter-ego. The fake Pentagon analyst Rapoport pretended to be caused so much trouble the Kremlin itself reported on it. Is this linked to Rapoprt’s death?

See omnystudio.com/listener for privacy information.

Episode Transcript

Speaker 1 (00:00):
Something strange is going on. Who is killing Russian billionaires?
Another Russian oligarch has been found dead. Reports suggests that
he hanged himself, fell out of a window, slashed his wrists,
was poisoned, murdered his whole family. Last year, more than
a dozen Russian oligarchs died in the space of nine months.

(00:21):
Many of the deaths are suspicious with links to the Kremlin.
This is sad Oligach, an investigation into these recently dead
Russian billionaires. It's created by me Jake Hanrahan and my
colleague Sergey Slipchenkov. Sad Oligach is a h eleven production
for Kulso Media and iHeartRadio. As we spoke about in

(00:47):
the previous episode, Dan Rappaport fell to his death from
the window of his luxury DC apartment on August fourteenth,
twenty twenty two, nine stories to the concrete. He was
dead at this His wife said she doesn't think it
was a suicide. He showed no signs of depression or panic,
and he had business meetings lined up that week, as

(01:08):
well as a lunch date planned with her the following day.
There is, however, the strange case of Rappaport's dog and
an alleged suicide note attached to the dog's collar. Dan
Rappaport owned a Ukraine rescue dog named Boy. According to
a Russian sauce which we'll talk about later, Rappaport sent

(01:29):
out Boy to the park before he plummeted to his death.
Boy allegedly had a suicide note and cash attached to
his collar, the idea being that whoever found the dog
would find the note and for some reason, the cash.
This is completely bizarre. If you're going to take your
life via jumping from the window of your own apartment,

(01:51):
why would you not just leave the suicide note on
the side, put it on the kitchen counter, leave it
on the coffee table, literally, anything would be more reliable
then attaching it to your dog and letting him out
into the streets. And what kind of lunatic lets their
dog loose into the city like that. Rappaport went to
the effort of saving Boy, bringing him back to the

(02:13):
US with him from Ukraine, which is a complicated process.
I find it hard to believe he'd then leave Boy
to the mercy of the streets where he could get
hit by a car stolen or put into the dog pound.
This whole scenario makes no sense. It does start to
make sense though, when you consider the source, but we'll

(02:34):
come back to that later. First, Sergei Jeff. In January
twenty seventeen, Russian businessman Sergei to Kachenko aka Sergei Jeff,
fell from the window of his luxury Moscow apartment. This
wasn't your usual Russian window plummet, though, this one was

(02:55):
caught on camera. In the grainy camera pH and footage,
Sergei Jef can be seen hanging from the window of
his apartment about fifty feet up. He's wearing black trousers,
a gray sweater, and looks to have no shoes on.
In broad daylight, Jeff is stood there, perched with his
feet on the sill of the window below him and
with his hands holding the upper sill of his own

(03:17):
apartment window. It's a precarious scene, to say the least.
Someone inside the apartment is at the window trying to help.
Apparently this was Sergei Jeff's girlfriend. The story goes that
the two had been having a blazing argument and that
Sergei Jeff decided to literally climb out of the window
of their apartment to hang from the building in a

(03:39):
bid to scare his girlfriend, presumably some kind of messed
up threat to kill himself if she left him, or
something like that. As my guess, at least in the footage,
Sergei Jeff loses his footing and begins to flail with
just his hands holding onto the window. His girlfriend moves
back into the apartment out of sight, perhaps looking for

(04:02):
something to assist her boyfriend. Before long, Sergei Jeff loses
his grip and of course falls to his death. He
was pronounced dead at the scene, with Russian emergency workers
bundling his corpse into a black bag on the pavement.
Several photos of this were circulated. The Russian authorities attributed

(04:23):
his death to what is essentially misadventure. I'm really not
sure what to make of this. That Dan Rappaport died
the same way as his soho room's business partner is
extremely suspicious when you take into account all the other factors,
such as Rappaport's anti Putinism, the taxi old, the Kremlin,

(04:44):
and his proximity to US politicians. After watching the footage
of Sergei Jeff falling to his death, though it does
just feel like an accident, making it possibly an incredibly
unlikely but actual coincidence. Is that or someone sent the
world's most inept hitman after Sergei Jeff. If you're going

(05:06):
to fling someone out of a window to assassinate them,
daylight is surely not the ideal moment to do so. Also,
a full shove out the window, as in keeping it
all in one movement, seems like the optimal way to
do so. Now. I've never pushed anyone out of a window,
and I don't intend to, but I imagine leaving a person

(05:27):
perched on the windowsill for a few minutes is not
only harder to do, but less effective than the aforementioned
full shove. That said, if there ever was a way
to make a death look like an accident, this convoluted
window method might be ideal. I don't know. I'm not
an assassin. It does seem unlikely to me that Sergei

(05:48):
Jeff was murdered, though, unless maybe someone else was inside
the apartment alongside Jeff's girlfriend and she was in on it.
There's no evidence that's the case. Though, this really might
just be a massive coincidence, So whatever happened. We do
know that Dan Rappaport met the same fate as Sergei
jeff a higher fall from his own apartment window. Rapperport's

(06:12):
situation is a lot murkier, though, Whilst on the surface
Rappaport might seem like a bit of a soft target
for perhaps a Kremlin linked hit that out of the
factors at play that could make him a target for
Oligarch violence. During the months leading up to his death,

(06:49):
Dan Rappaport was openly complaining about a sour deal with
a Russian venture capital firm. He'd apparently been stiffed out
of around ten thousand dollars details of scarce. From what
I can gather, Rappaport either invested in or was owe
the money by an unnamed Russian BC company. Yes, he
was doing business with Russia in twenty twenty two, even

(07:12):
as the Russian invasion of Ukraine raged on, something Rappaport
was very openly opposed to. Now you might be wondering
why a multimillionaire would care about a ten thousand dollars loss.
I think in this case it's quite simple. It's the
principle of it. He didn't care so much about the money,
but he did care about getting screwed on a deal.

(07:34):
That's pretty straightforward and I think understandable. Rappaport wanted to
drag this Russian VC company through the mud to try
and ruin their reputation after they messed him around. In
April twenty twenty two, he posted about this VC scenario
on his Facebook page, somewhere he was often very vocal

(07:54):
and active, and he messaged a friend about it, saying, quote,
I need a small favor. I just posted on Facebook
about a Russian BC firm trying to screw me for
ten K. I would really appreciate if you could like
and or comment on it. I don't expect to get paid,
but I want to maximize their public embarrassment. Ends quote.

(08:14):
Whilst little more is known about this situation, it does
show that Rappaport had more than a few active dispute
links to Russia. At the time of his death, the
Kremlin had shut down some of his businesses and accused
him of tax evasion. He was openly backing one of
Putin's biggest enemies, with Navali. He supported Ukraine. He was

(08:35):
a vocal critic of Putin's authoritarian rule he had a
dispute with a Russian VC firm, and he even worked
with the US government to try to increase Western sanctions
on Putin. Rappaport was not in the Kremlins good books,
to say the least. He was a high profile Putin critic,
and by association was a problem for anyone who thrives

(08:56):
under Putin's iron rule, as he had done for several years.
Despite his constant agitation against the Russian state and his
many dealings within it in the past, Rappaport did not
keep a low profile. He was bombastic in his messaging
and frankly a bit of a show off. He'd often
be photographed on the socialite scene, frequenting upmarket venues in

(09:18):
his expensive suits and designer glasses. He'd post for photos
outside the White House wearing a Ukraine badge on the
lapel of his suit. In the months before his death,
he posted photos of himself surrounded by beautiful women in
the shanky Connaught Hotel in London. A room there costs
over five hundred pounds a night. Rappaport was a businessman

(09:39):
who enjoyed the finer things in life, and he wanted
you to know about it. What he shared, though, was
what he wanted out there. What he hid was quite different.
Rappaport had a serious secret identity. In twenty eighteen, four
years before Rappaport died, a DC based journalist named Alexei

(10:01):
Kuzumenko dug into the background of a man named David Duberg.
David Duberg was a senior Pentagon analyst on Russia released
that's what he claimed. Many journalists claim this about duw
Berg too, citing his work without question. David Duberg ran
a popular Facebook page and he was regularly quoted in

(10:24):
the media as a Pentagon insider when it came to
Ukraine and Russia. However, the journalist Kuzumenko discovered that du
Berg was not quite who he claimed to be. Kuzumenko
didn't want to be interviewed for sad Oligarch for whatever reason,
but his work on this is very revealing in itself.
It seems that David Duberg, the Pentagon insider often cited

(10:48):
as a real life analyst, was actually a persona set
up by Dan Rappaport. Not only that, but to keep
the ruse looking authentic, Rappaport falsified identification dot Com documents,
including a Pentagon idcat. This is a crime in the
US and could get you as many as three years
in prison. What the hell was Dan? Rapoport up to

(11:12):
the David Duburg alter ego have made an appearance online.
In April twenty sixteen, Ukrainian new site named Dialogue dot
ua announced that Duwburg would be writing for them. They
said that he was an American soldier analyst, military history specialist,
officer of the US Army, political consultant of the US

(11:33):
State Department, Department of Defense, and national security analyst. The
full ticket Dialogue dot yua went into great detail about
this fake new writer David Duberg. They spoke about his parents,
his high school, and how he was raised. They said
Duburg had been previously deployed to Somalia, Yemen, Kosovo, Afghanistan,

(11:54):
in Iraq. He was a lieutenant colonel before becoming a
senior analyst for the US Department of Defense. They even
included a photo of du Berg, a muscular white guy
dressed in olive drab and a backwards cap, and the
photo is leaning over one side of his pickup truck
with one hand cuddling his dog. Wholesome based on his forearms. Alauren,

(12:16):
This supposed Duberg character looks like he can bench four
plates with ease. He's pretty much a routine tooting US
soldier archetype. Compare this to Dan Rappaport. A man had
never been to war, he was skinny, and he wore
slim fits suits and shirts with loose buttons. Was David
Duberg Dan Rappaport's tyler Durdham, I want you to hit

(12:39):
me as hard as a key In the article, it
says quote. From spring twenty fifteen to Autumn twenty seventeen,
du Berg maintained a popular Facebook page written predominantly in
fluent though somewhat Americanized Russian, with occasional posts in English.
The Facebook was originally started in May twenty fifth Dean

(13:00):
and quickly began its rise to prominence. This was a
time when President Obama maintained a relatively reserved stance towards
Russi's aggression in Ukraine. We s them peaked in February
twenty fifteen with the Battle of de Boltzeburg. Many in
Ukraine and those among Russian anti poutine circles sought a
stronger stance from America against the Kremlin, either through direct

(13:22):
action or in rhetoric. Du Burg presented as a public
source from within the Pentagon, appeared to fill the latter role.
Along with his Facebook profile, du Burg maintained a public
LinkedIn account, a Google Plus profile, and a website at
du Burg's list dot com. Du Burg's LinkedIn profile bolstered
a sense of legitimacy, where he displayed his connections with

(13:44):
a number of well known Russia watchers, including Michael mcfull,
the former US Ambassador to Russia, David Satter, a prominent
American Russia expert and historian, and Mark Golotti, a prominent kremlinologist,
and many others. Furthermore, he had a number of endorsements
for various skills, a feature in LinkedIn that gave his

(14:05):
profile a sense of authenticity ends quote. So through David Duberg,
Dan Rappaport was building a fictional yet highly believable profile
of an anti Putin Pentagon analyst with all the right credentials.
David Duberg was an intelligent, tough guy who was heavily
critical of the Kremlin. Problem was, he didn't exist. David

(14:29):
Duberg's Facebook page was a collection of boomer esque Patriot
type iconography, not far Ride or anything like that, just
your average West is Best type vibe through Duburg. Rappaport
was at that time promoting US Russian friendship with a
Facebook banner of what is one of the worst designs

(14:51):
I have ever seen in my entire life. It's two
hands reaching out fist bumping with a pen in the
middle of them that's made out of a bullet. The
left fist is painted in an American flag and the
right fist is painted with a Russian flag. It looks
like a gas station energy drink. It is an absolute disaster,

(15:12):
and in that way, it's kind of perfect. That said,
the page does look very legit. The bio says, quote,
I'm a veteran of the United States Forces. I'm of
Russian descent. I blog on history. I wrote the truth
and facts all that is being hidden from Russians by
the Russian state media. Ends quote. There are numerous other

(15:33):
photos of this supposed David dubog fella with other people.
There are photos of this guy wearing military dress uniform,
dripping in medals, a photo of him carrying a leopard
for some reason, and a front line looking photo. He's
in full deployment gear, helmet, body armor and of course sunglasses.

(15:53):
But he has a Freemason patch Velt roode onto his
chest drink. The Freemasons being a global secret also pretty
much open society, made up of usually wealthy men of
some public standing. Conspiracy theorists think that they rule the world.
In reality, whilst they are a huge club of well
connected people, they're not that powerful. Freemasonry can and has, however,

(16:19):
become a breeding ground for elitist cliques. In my decade
of reporting from front lines across the world with regular soldiers, militias,
paramilitary forces, you name it, I have never ever seen
a Freemason patch. I've seen many different patches, I actually
collect them, but I have never seen a free Mason

(16:41):
patch in a conflict zone. Naturally, that stood out to
me clearly. The guy Rapperport, howevers, did these images from,
was associated with Freemasonry. Either way, Rappaport did a very
good job of deceiving people with the David Duberg profile,
but didn't exist. So who is in the photos? It's

(17:04):
Steve Ferrow, one of Dan Rappaport's college friends. This guy
isn't Russian, He's from Texas. In fact, in some of
the counterfeit juburg id cards Rapperport had made. The ID
photo of Duburg is poorly photoshopped from group photos of Ferro.
This level of deception is a lot of work, but

(17:25):
to what end. Let's hear what Kuzomenko wrote about this quote.
Kasenya Kirilova, a Russian journalist who was relocated to the
United States, was an early witness to the rise of
David Duberg's profile and influence online in the growing interest,
especially among those in anti Kremlin activist and opposition circles

(17:46):
in the United States. Kirilova said that in twenty fifteen,
everyone in the close knit Russian opposition community in the
US was talking about David Duberg, the new vocal anti
poutin Pentagon official. Kirilova said that in twenty fifteen, being
a fresh arrival to America after immigrating to the country
a year earlier, she struggled to connect to established American

(18:09):
experts in her field of Kremlin and propaganda studies. Her
friends in her new home, including other members of the
Russian opposition community, pointed her to Dubug. As Kirilova describes,
Duburg was highly effective as a tool of counter propaganda
during the heights of Kremlin organized this information campaigns, David
Duberg enjoyed tremendous support from numerous individuals. On occasions he

(18:34):
posted materials that really could highlight Russia's state under Putin.
He was supported not because the public was dumb. He
enjoyed support of smart, decent people who use some of
the material he provided in their own online argument with
pro pouting crowds. David Duburg endeared himself to many within
Russia's opposition and in Ukraine when in the summer of

(18:55):
twenty sixteen he penned and urged his followers to also
send a letter to Facebook's managers urging the company to
address its moderators alleged pro Kremlin bias ends quote. Clearly,
David Dubo was more than just a Facebook profile. Rappaport
was in a sense infiltrating his own community US based

(19:17):
Russian anti Putin dissidents. But why well, My guess is
people are less likely to listen to a former gas
sales middleman turned nightclub owner who made millions under Putin's rule.
Du Burg was nothing like that. He was an urra
us soldier with Russian heritage and the feeling that America
is always in the right. It's a much easier sell

(19:40):
that said, I don't think what dubog said was radically
different from what Rappaport himself actually thought. It was just
dressed up in a lot of nonsense. Said nonsense worked though.
Duberg was promoted by influential people in the scene. Slava Rabenovitch,
a Russian American financer and blogger with nearly twenty five
thousand fi Facebook followers, called Duberg his friend, and Alexander Suttnik,

(20:05):
an opposition journalist and activist with over one hundred thousand followers,
promoted Duberg's writing. Duberg's influence grew when he was invited
onto a conference call with Facebook managers and Facebook Global
Head of Content Policy to speak about Krimlin propaganda operations
on the site, something that actually has real world significance.

(20:27):
Due to many people's inclination not to question what they
read on the Internet if it comes from an alternative perspective,
many people literally believe my side good, other side bad,
everything against my side propaganda. This is a bipartisan issue,
trust me. So Duwberg was making waves in twenty fifteen,

(21:04):
he was noted in Ukrainian media when an article was
written about one of his many Facebook screens. The article
was titled ten days will Suffice a Pentagon official gives
a detailed description of how Russia will lose a war
with NATO. Many reporters and propagandists shared Uberg's work and
critically even interviewing him via email without double checking any

(21:27):
of his credentials. Sadly, especially in conflict reporting, journalism sometimes
takes a back seat in favor of pr if it
concerns the perceived good guys. It's wrong, but that's how
it is, especially when social media fame is in the equation.
So anyway, David Duberg was ostensibly speaking on behalf of

(21:49):
the Pentagon, or at least he was projected that way.
He was making wild statements about war that would give
Ukrainians and anti Putin Russians a false sense of secure.
What Rappaport was doing here was pretty terrible, to be
honest with you. By twenty sixteen, David Duberg was hot property. Union,

(22:10):
a major Ukrainian information agency, ran two pieces on Duberg.
A Russian ATO war Pentagon analyst predicts how it could
look and how it will end, and Pentagon weighs in
on the possible scenario of events in Dombas Putin's perspectives
Focus dot Yue published Pentagon gave its prediction of the

(22:31):
future of Dombas the hugely popular Sogodya dot Yue published
Pentagon gives valuable advice to Ukraine's armed forces and Pentagon
explains Russia's aggressive international posturing. On the same day, Ukraine's
highly popular television channel ICTV also quoted Duburg in news

(22:52):
items on its website, including Russia's defeat in the Dombas.
The Pentagon gave details and the U speaks on Kremlin's expectations.
As you can see, he's creating a false sense of
security for Ukrainians. Around this time, the Kremlin took notice
of David Duberg too. Remember he is Rappaport. Rappaport is heat,

(23:18):
so the Kremlin also took notice of Dan Rappaport. As
Jewsamenko writes, quote Dubog was brashed to the point of
being offensive and equal part anti Putin and patriotic to America.
David Dubog was just the kind of an American many
in the Russian opposition craved. His statements also pleased Ukrainian

(23:40):
online crowds, eager for an insider perspective affirming the belief
that America and its military minds were firmly on its
side in its ongoing war with Russia and its proxies. However,
these same traits that endeared Duberg to Putin's foes in
the fall of twenty sixteen turned out to be in
high demand for Russian media looking for confirmations to the

(24:01):
image of the warmongering, russiaphobic Pentagon long promulgated by the
Kremlin anti American propaganda ends quote and so Duwberg's comments
began to pop up in Russia's Kremlin run media organizations.
Regnum dot Iu posted an article titled Pentagon speaks up
on NATO's war against Russia. It will be a war

(24:23):
of rifle against the laser gun. Du Berg is cited
as a US Department of Defense analyst. As you can see,
rapperports bullshit began to catch up with him. Now, believe
it or not, there's still so much more to this story.
Sergeimy had been going over it, and this one really
deserves a little more time. To boil it all down.
There's a lot of information in this case that we

(24:46):
just can't glide over. The end will be spectacular lo
something like that. In the next episode, the final part
of what's first becoming a Dan Rappaport subplot, we'll discover
who first blew the whistle on his death and how
the David Duberg fraud was exposed. Sad Oliger is a

(25:07):
H eleven production for Cool Zone Media and iHeartRadio. Hosted, produced, researched,
and edited by me Jake Hanrahan and Sergei Slipchenko. Co
produced by Sophie Lichtman. Music by Sam Black, artwork by
Adam mcdoyle, soundmix by Splicing Block. Go to Jakeanrahan dot

(25:30):
com for more information.