Why Was Puerto Rico's Lottery Leaking Millions of Dollars a Month? 💸 Darknet Diaries Ep 101: Lotería

In 2014, the Puerto Rican lottery was mysteriously losing money. Yet, a complete audit of the drawing and the accounting showed no issues. That's when one penetration tester got the green light to go deep, and uncover a scam so dangerous, he had to leave the island.
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[@Gixsir]

Jacks dad listening to the first 2 minutes punching the air 😂

[@user-px1wj2uv3r]

Something I think goes somewhat unnoticed on this channel is the artwork. Seriously love the stories man, I'm addicted, but damn the artwork is always super cool too.

[@randoir1863]

There are 2 guarantees in life : death and taxes . What a crazy ass episode WITH a twisted ending . Ty Owl Stalker and Jack for great episode.

[@henlofren7321]

Can't tax me if I refuse to work :)

[@mr.lorenzo3620]

From puerto rico and i had no clue this was going on… Love your videos, as a cybersecurity student your videos are a great break from studying while also keeping me informed on amazing cyber stories!

[@tipsfromjuan]

En cualquier parte del mundo siempre hay otro Boricua! 🤜🏻🤛🏻

[@user-ev3yt1rg2g]

Que duro también soy estudiante de Cybersecurity y no pensé que PR fuera mencionado en el show…

[@jazztheglass6139]

@@iespinosa31 my auntie lives in the Virgin islands one of her old neighbours won something over a million about 20 years ago. He spent a good chunk on a fishing boat, fell overboard and drowned. It was very sad

[@ItsFrankieFigs]

Oye Boricua. I’m studying Cybersecurity as well. I’m new, and hearing the story’s, words, the lingo, is helping me tremendously.

[@baoboumusic]

@mr.lorenzo3620 love your island! And hope you guys have recovered a bit from the 2017 hurricanes, not to mention from other destruction (including political). Great people, beautiful island, tough situation.

[@Omgitsmario100]

“Playing games” on his computer… OK Jack 😂

[@altimmons]

Yea we all read between the lines

[@ryanfrank1309]

This Marine was his platoons expert ball examiner. Absolute legend.

[@mikedirl]

are you the only other comment besides mine that could 100 percent tell this guys was absolutely lying and had no clue what he was talking about? I hate to say it, but i am a 20 year red team operator for everything from our government to currently a fortune 100 federal defense contractor...This dude jack just talked to did not sound like he has ever ran a network scan, let alone actually operate...what a loser...jack, delete this episode, its all love from me, but do not make my life profession look bad with wanna-b's like this asshole.

[@A.C._]

The secret is in the balls, it always is....

[@f86tune48]

😂😂

[@xCheddarB0b42x]

Happy Birthday, United States Marine Corps. Here, enjoy this crayon cake from the Navy mess. :}

[@RILEYLEIFSON_UTAH]

Great interview. Would have been EXPONENTIALLY BETTER if dude [OZ] could've managed to speak like a professional for a mere 70 min.🙄 It's one of my biggest pet peeves in the world when people talk like this!! WHYYY!? Why the need to say f**k before, after and during every point in the story?? It's juvenile, unprofessional AND just plain TRASHY. Do people not realize how much dumber (literally) it makes you sound? I'm talking < 81 IQ status. (Or closer to < 74 IQ realistically) Those who don't agree with me probably talk exactly like Oz and therefore see nothing wrong with it, or think there's nothing weird about it. Welp...I hate to break it to ya bud...buut you're wrong. Pro Tip: Don't talk like this. Trust me.

[@swazs6092]

30:26 Him getting a full immunity card sounds cool, but also very scary.

[@carnivorebear6582]

Unfortunately only grants him immunity from the government, not the cartel who would honestly do much more

[@reedleatherware]

Ah man! Ive been binging your channel for like 9 hours now. Stoked to have found you. Thanks a ton for all your work. 💪💪

[@Goodluckgabriel201]

He has more episodes on the website when you're done with the videos

[@xCheddarB0b42x]

They're great stories.

[@brettrossi034]

How do you do it Jack? How is your timing so impeccable? I worked all night, clocked out at 4:45 am, loaded up a video to watch after work while i unwind and eat and the first one to pop up is a new Darknet Diaries! Thanks buddy! Love the show

[@jackmiller8851]

Look Brett, I don't know how to tell you this, but the RFID arse plug isn't a secure means of pleasure. Mr Rhysider is proficient in all forms of penetration, up to and including electronically scanning your colon. Better fill those gaps buddy.

[@jacrispycracker]

Always first in my feed too. Best stories to unwind too!

[@jdwar11]

truly amazing and i was hooked after the first one of his audios.

[@samzimmerman2621]

His enthusiasm to examine the balls is amazing.

[@South_0f_Heaven_]

Another great episode, Jack. I love how you describe it so that a normal person can understand what you’re saying because a lot of people obviously are not network engineers but the way that you narrate the video is perfect.

[@codezerodnb]

"The cartel" made me laugh so hard my neighbor had to ask what was going on. That was an inside job and politicians were involved.

[@pkninja3286]

Has it been two weeks already? Thanks for covering a Puerto Rico story!

[@7_of_9]

The Puerto Rico Lottery (Lotería de Puerto Rico) was first authorized in 1814 by the King of Spain and was put into law in 1934.[1] It is operated by the Puerto Rico Department of Treasury

[@jasemkhl217]

Hahaha a proximity sensor. What a gangster

[@Shadow-Veil]

I'm from PR and it's the first time I've heard of this

[@encoded7403]

I remember this intro story

[@mikedirl]

of course its the first time you have heard of this, none of its true...this episode is a joke right? because from a red team operator, here, who has been hacking for the united states, multiple fortune 500s, and currently a fortune 100 defense contractor, i am telling you the fucking moron in this episode has literally never been on any engagement, pentest, or anything even close in his fucking life. I literally am not sure whats up with this episode jack, but start vetting your people bro, this is almost sad how many things dude said that literally made me laugh out loud and shake my head.....you have legit GREAT episodes, like Jeremy from marketing (J.strand sent me the comic early, was fucking SWEET!) and then further down the road, you are starting to fall the hell off hard....just vet your people bro. I could tell after 10 minutes this dude has probably never used nmap let alone any real pen tests/red team engagements/ops besides what he has fantasized about a line of work, that i have done for 20 years now, in which someone like him probably would never even be capable of attempting to become a professional based on how fucking low his iq must be...Jesus, if you want i will llisten to your stuff for FREE before you release it and make real red team operators look llike trash.

[@TylerSmith-qx6uz]

Probably because this guy made the whole thing up, jack needs to do a better job vetting these guests.

[@clockwork9011]

@@TylerSmith-qx6uzcan you substantiate your claim?

[@jamesabernethy7896]

I found your channel about a week ago and I LOVE it! Although I do watch a few channels which cover mysteries and investigations, this still felt very random when it just came up as the next video on the autoplay. Terrific presentation and really natural interviews that don't feel coldly clinical. I like the little touch of life in your background and the touch of melody just keeps our focus centred. Even though I am sitting listening to this from the comfort of my own home, the feeling I get late night radio with a voice guiding me home. A really well-crafted format and the thumbnails are so effective and evocative.

[@xCheddarB0b42x]

welcome! enjoy the ride.

[@djwindkind]

Dude, I am so in love with your pods! Never stop!

[@brokens1097]

Possibly the best tec story ever told, certainly a contender in general. Great job on this one!

[@JJBACS]

This is one of my favourite episodes so far. Great journalism.

[@SgtCrypto]

“Get Rich or Die Tryin’” I saw what you did there 😂

[@dooooooval904]

If you were doing something you didnt want your dad to see you shouldnt be doing it in the first place! ....but weve all been there lol.

[@sicabeat]

the anecdote about his dad... i guess that's a shared universal experience 😄

[@Big-Timbo]

Yesssss I wish I could listen to a new ep every day!

[@iamheretojudgeyou]

What a nice surprise, thought we had couple of weeks wait for new video/upload top work Jack!!!

[@jackmiller8851]

As a man, I'm also quite interested in the physical security of the balls.

[@billionabil]

Intro animation is dope!

[@Nackss]

I didn’t know Crush from finding Nemo got into cyber security. Great episode.

[@0therun1t21]

This is one of the top two orc three scariest pen tests I've ever heard, all on this channel of course. This might be the scariest, cinsidering how certain groups operate, it's a good thing this guy isn't a resident of the island, but still. The joke at the end, lol!

[@mikedirl]

Unfortunately, the guy in this story made everything he said up... For people like myself, who actually do these things for a living every single day, this was the hardest episode to listen to, I legit could not finish it, especially since the guy lying isn't smart enough to write a bash script let alone do a pen test... But if you were entertained, then all good... Just do not look at this episode to try and analyze anything that goes on in reality when it comes to Penn testing red teaming or how this story actually went and the real people that were involved... Episodes of Jack's with for example the commander who helped take down ISIS media now that is a real deal engagement story / cyber operations that you can take to the door my friend, everything he said including about himself hacking for the US government to take down ISIS and all of its infrastructure was absolutely 100% accurate

[@dendrites]

⁠@@mikedirlHow do you figure? This job didn't require any elite hacking. He used off-the-shelf exploits on old systems with known exploits and poor network security. Also at the end Jack looked up the court records and it confirmed everything that was mentioned in the story.

[@0x8anon]

Hahah no ways that Jack mentioned a 50 cent quote in the end 🤣🤣🤣

[@Young_buck2423]

doing the drop off at the mall is kinda baller

[@Infinitespace04]

Thank you, OS and Jack. Such a fantastic story

[@SALTINBANK]

Loved the intro : when i was 13 y old my Dad don't want me "faire le mur " (playing hooky) like we said in french, from a party from friends i should left the party before 23 : 00 PM but i knew he would fall asleep before Midnight, i went back at 6 AM in the early morning and repurposed all the clocks in the house to 12 : 00 AM ... Made my entry will lot of noise, like i was going in the house ... He said me : Son, you are late ! Time to sleep ! Couples of hours later all the clocks were giving the right time (post exploitation). 20 years later : my first hack and social engineering skillls.

[@WayTooMuchPressure]

This is quickly becoming my favorite YT show. Fascinating stuff man!!

[@milenakavka8337]

Started with a Dad story and ended with a Dad joke, nice touch. Loved the episode, thank you 🙏

[@ardeladimwit]

well, newspapers aren't as fun as the bucket of water over the doorway.

[@rikvermeer1325]

Another great one. The ending is just insane! Thanks Jack!!!!

[@Nopejams]

I mean if the cartel comes up to you and tells you to do something it is either die there or do what they ask

[@fyutffdtuibgfetu]

This could be a Netflix series

[@AnotherDred]

They would effed it up but it's a great Idea!

[@CaptainMarget]

Netflix ruins everything. This could be a visual medium*

[@TylerSmith-qx6uz]

This guy sounds super full of shit

[@mikelmikes310]

What an ending to the podcast. WOW!!!!

[@ardeladimwit]

strange that OS didn't just ask the governor for the floor plan of the building. It would have saved him some trouble to have the layouts

[@MuzzaHukka]

Or give whoever is guilty a heads up and idea of where someone is going to be looking for clues.

[@ardeladimwit]

@@MuzzaHukka floor plans are usually public documents as they are architectural drawings and have to be approved before construction is done--duh? and whoever hired him to investigate would/should probably have access to something so basic. you're too deep into conspiracy theories to be pragmatic.

[@MuzzaHukka]

@@ardeladimwit the governor of Puerto Rico is still less than a state senator. He has the US government to answer to, above him. Either he, or someone working in his office, or someone who could have planted a bug in his office, could be intercepting communications between OS and the governor. If OS sends a message "hey, I am going to be investigating computers in building X", anyone who is tech savvy will think "oh shit, we can't leave any evidence/computers/cabling that can be used to pentest the rest of our network in building X". It's like a corrupt cop getting tipped off about his evidence room being searched in the immediate future... He might start a fire or go over everything with a fine brush to get rid of traces. OS going into the lottery place without getting noticed, most importantly by people on the inside, is what allowed him to monitor the inside job dude without him getting tipped off that someone was even aware of/capable of figuring out who he was.

[@Sawta]

Man, that story took some serious turns towards the end there. Wow!

[@saucymoon7134]

I thought you were taking a 2 week break after episode 100. Thanks for the new video

[@sunnia1989]

Duuude!!! This episode is nuts! Thankyou!

[@collins_channel8643]

50 cent is loving the last line lol

[@sergiol.3755]

was not expecting that ending

[@ITZZZJOHNYYYYY]

booom after a all nighter this is what i need for that last hour respect!

[@MangoKitty]

Real cool episode today jack 👍

[@GreatNW]

I don't know about half the stuff you talk about on here but the stories are very interesting

[@pmally2006]

He got to touch the balls 😂

[@JoeVannoy]

Dude. Recently, you've had some of the coolest guests

[@asailijhijr]

This sounds like the racket in the movie Looper.

[@joeyunlockstheworld]

Heyy they weren't stealing they were just washing their money 😂

[@JoseValencia-fr8wh]

The story you told on the start up to 2:15. That's dope. Your dad sharpened you up.

[@GravityHater]

Your dad opening your mail is a FELONY 😅

[@Chewy_GarageBandDad]

They are essentially stealing from the store. How is it the store was not coming out 10 thousand in the hole?

[@andrescorrea125]

Im from Puerto Rico and this shit is new ..... but does not surprise me .... the goverment aint that good in cyber security

[@hernancortez491]

This slowly cradles me to sleep at night…awesome👌

[@0x8anon]

Love your podcasts Jack!!!

[@andrescorrea125]

I remember in school in Puerto Rico, our computer classes were with winfows 95 or windows 2000 ... lol ( this was on 2008 to 2010

[@wheresmymoneyat2482]

"linge/able" = a podcast that's fun/easy to listen to for hours on end; binge; bingeable noun: darknet diaries

[@johnross779]

There's plenty of information being left out .

[@inifin8]

This deserves a movie

[@redrum4486]

As someone who frequently updates databases, i was thinking wtf throughout this story LOL

[@ozpoint2517]

¡Queeee cuando esto sucedió! Yo se que hackearon el autoexpresso pero ¡¡la loteria!!, es increíble.

[@fabiopimentel6981]

This episode is pure gold man 🔥

[@xportal9169]

The best podcast so far. Subscribed 🎉❤

[@anpeck464]

This has definitely been one of your best episodes ever!! The main story is cool but the ending is unexpected.

[@zaelectricalltd1]

Yet another great episode Jack .

[@_KARMA_78]

'PRIME-8s?!' 😅🤣🤣 DORK!! 😂😂 AND YES, LOVED YET ANOTHER OF YOUR STORY TELLING MIND CONTROL ABILITIES. VERY PRIMAL INVOKING, INDEED. 😎

[@mcollins630]

Your guest doesn't sound old enough to have been alive during the warez days.

[@TiagoTiagoT]

What's the point of letting investigators break laws in their investigation? I mean, doesn't that makes any evidence collected not allowed to be used in the trial?

[@UBvtuber]

I forgot the name, but there's a practice of law enforcement using illegal means to find something out, then later using legal means to find it and cover themselves in court.

[@xportal9169]

The most underrated podcast no doubt

[@NowayJose14]

Fascinating story! So wild!

[@jasonsoto362]

Ugh your on fire with you podcast

[@brentandvuk]

Thank you, this was a great episode

[@f86tune48]

Holy fuck this story was captivating

[@theshovl3r]

Just a tip, when you go into federal criminal court 99% of the time the plea is not guilty. No matter what. It’s not an indication of there intention to plea guilty later.

[@rainmetal]

Hey Jack, this was a good one brother...much love to you man.

[@illumistration]

Man that was one of the best whodunnit videos of all time, had a lot of fun listening to this one.

[@franciscolopez2736]

great stuff ❤

[@patrick764]

Very good episode.

[@antoniobruce6579]

When i grew up in PR I always suspected there was something weird at that mall!!! Plaza Las Americas in San Juan

[@bumlookercheekymonkey3985]

Funny I can barely turn on a computer but I love these stories 😂😂😂.

[@aleksanderczajka6072]

You get a like just for the proximity sensor XD

[@THEMAX00000]

How can someone be tricky in their own house?

[@theoreticalexercise]

I remember this episode and i still listened all the eay through again. So interesting 👏🏾👏🏾

[@CryptoDealerz]

Again great content 👍🏻👍🏻

[@napierpaxman]

The govener gave him permission to examine the balls.... :D

[@Massenko]

I love this podcast!

[@DanielSandhu-jo4jj]

Am I tripping or is this a re upload ?

[@THEMAX00000]

Really great story. Guy got some discipline early on in his life and turned out OK.

[@trail_mix24]

I love his comment on not realizing the marine corps is just trained to kill. Reminds me of when i joined the Navy and forgot that it involved water

[@inappropriatejohnson]

OK......that was good. Rippin good. Thanks

[@killitgameing658]

Requiring to be online to run a game doesn't actually make it really any more difficult to crack, and pretty much every circumstance ever of these companies using online-only DRM, it's only hurt players who actually paid for the game.

[@brianbrett7966]

Love this one

[@mirkmusicyt]

Hey, I enjoy your videos but your microphone quality has seemed to be degraded recently is there a reason for this?

[@samram8489]

Love your jokes bro! awesome content.

[@xCheddarB0b42x]

"warez?" Man, that takes me way back.

[@cybermunchkiin5689]

Puerto Rican Cybersec pros rise up!