INTRO: Jailbreaking was one of the biggest parts
of my childhood.
Whenever Apple released a new version of iOS, the entire jailbreaking community would come
alive.
We would see dozens of videos covering the latest exploits and kernels until we finally
got the latest jailbreaking tool from OGs like redsn0w, limera1n, Absinthe, TaiG, and
Pangu.
Sometimes, these tools were only capable of achieving a tethered jailbreak which meant
that you had to plug your phone into a computer if you wanted to reboot your device.
I remember always avoiding the tethered versions and impatiently waiting for an untethered
version.
In fact, I used to stay on the last major version of iOS until an untethered jailbreak
was available for the new version.
All of this was just so that us Apple fanboys could have a few cool tweaks that made our
devices unique whether that be getting dark mode, customizing the carrier text, setting
up widgets, creating video wallpapers, and so on and so forth.
And the platform that made it all possible was Cydia.
If you’re not familiar with Cydia, it was basically the app store for jailbroken devices.
This is where you would add new sources and download the latest tweaks.
And whenever you opened Cydia, one of the first things you would see is that it was
created by a man named Jay Freeman also known as Saurik.
I always wondered who this guy was as a kid, but ever since I stopped jailbreaking, I completely
forgot about him until today.
So, here’s the story of Cydia’s founder and what he’s up to today.
JAY FREEMAN: Taking a look back, the story of Jay Freeman
dates back to November 27, 1981 to Chicago, Illinois.
We don’t really know much about his early childhood, but I think it’s safe to assume
that he was pretty involved coding and tech given that he was publishing papers and launching
software from very early on.
For example, in 2002, Jay built a decompiler called Anakrino for the .NET framework.
If you’re not familiar with decompiling, it’s basically reverse engineering software.
Whenever you write a piece of code and run it, the computer will compile the code and
convert it into something that it can understand called machine level language.
Oftentimes, this means converting everything to 1s and 0s.
Building a compiler itself is quite complex given that you have to account for so many
different factors such as errors in the code.
However, this is not what Jay was doing, he was decompiling software meaning that he was
trying to convert 0s and 1s back into english code.
Now, I can’t understate how difficult this is.
Whenever you compile code, computers don’t just directly convert it into 1s and 0s.
Rather, they play around with the code to increase efficiency, reduce redundancy and
so on.
So, trying to piece back the original code is usually a nightmare, yet Jay was voluntarily
developing such software when he was just 21 years old.
Looking back though, it makes perfect sense that Jay was interested in such a project.
Anyway, around the same, Jay would attend the University of California at Santa Barbara
where he studied computer science.
It seems that even though Jay was a massive fan of learning, he wasn’t the big fan of
traditional education.
In fact, his high school grades weren’t that great.
However, all of this changed when he reached college.
You see, his school allowed students to propose and teach classes under the guidance of professors
which quickly became one of Jay’s favorite activities.
In fact, Jay liked this so much that he would actually end up spending 10 years at UC Santa
Barbara.
After he completed his bachelors in 2003, he would turn around and become a doctoral
student for the next 5 years.
I don’t think Jay’s primary focus was getting the degree itself.
After all, he never got the degree despite pursuing it for 5 years.
Rather, I think what Jay really wanted was to interact with knowledgeable peers and conduct
research which is exactly what he did.
In 2005, for example, he coauthored a research paper called “Java Runtime Event Specification
and Monitoring Library”.
College wasn’t the only thing he did either.
Throughout his entire college career, Jay held down various tech jobs as a software
engineer, a software consultant, and a chief technology officer.
Considering this extensive coding background, I don’t think you’d be surprised to hear
that Jay learnt iOS development as soon as the iPhone was released, and that brings us
to the creation of Cydia.
FOUNDING CYDIA: One of the first applications of Cydia can
be tracked back to an iPhone video recorder app called Cycorder.
Nowadays, a video recorder app might sound trivial given that video recording has been
a standard feature of smartphones as long as we can remember.
But, there was a time when iPhone’s could not record videos, they could only take pictures.
In fact, it wasn’t ill iOS 3.0 that Apple launched the video recording feature and it
was only available to people who owned to latest iPhone.
Older iPhones didn’t support video recording even though their hardware was technically
capable of it.
So, Jay decided to take this issue into his own hands and create Cycorder.
And it seems like Jay was able to get the app working just fine even on the older iPhones.
But, when he tried to post the app onto the appstore, Apple rejected it.
In such a situation, the average developer would probably just be upset with Apple and
complain to their peers, but Jay had a far different idea.
Since he couldn’t post the app onto Apple’s app store, he decided to launch it on his
own app store that could install apps onto iPhones without Apple’s permission.
At the time, Apple’s software wasn’t the most secure and jailbreaking was likely not
something that Apple even gave much weight to.
So, it wasn’t that hard for Jay to use his coding skills to leverage root access and
create Cydia.
Fun fact, Cydia was launched even before Apple’s app store in February of 2008.
And given how limiting Apple’s software was at the time, and given that everyone who
had an iPhone were already tech enthusiasts, it didn’t take long Cydia to go viral within
the iPhone community.
In fact, by August of 2009, Cydia boasted 4 million users, and considering that only
40 million iPhones and iPods had been sold at the time, 1 in 10 owners had jailbroken
their device.
For obvious reasons, Jay would drop out of his doctoral program around this same time.
All of these users weren’t just for show either.
While Cydia was an open source project, Jay ensured that he and and his peer developers
would all be paid.
Many of his apps like Cycorder displayed ads which allowed him to earn some money.
Similarly, paid apps and tweaks could also be listed on Cydia.
Now, a lot of people would just use third party repositories to basically pirate these
tweaks.
But, fortunately, many tech enthusiasts wanted to support these developers and they would
pay for these tweaks.
By April of 2011, Cydia was pulling in $10 million in revenue per year.
Unfortunately, when all of the operating expenses were taken out and everyone was paid, Jay
was only left with roughly $250,000 per year which is only a 2.5% net margin.
Fortunately though, Cydia would only continue to gain popularity as iPhone sales exploded
in the early 2010s.
The problem though was that as Cydia gained popularity, Apple became more and more annoyed.
APPLE STRIKES BACK: One of Apple’s first responses to any jailbreak
was to patch it as soon as possible.
After all, to gain root access into an Apple device, you had to leverage some sort of security
flaw.
So, when you really think about it, jailbreakers were actually providing free security consulting
services to Apple.
Anyway, as Apple patched one exploit after another, it became harder and harder to jailbreak.
Even though more developers were working on a jailbreak, it took longer to actually come
up with a reliable version.
We also started seeing more restrictions when it came to jailbreaking.
For example, certain jailbreaks would only work on certain devices, and untethered jailbreaks
became less common.
Aside from fighting the jailbreaking community head on, Apple also tried to dissuade customers
from jailbreaking their devices by claiming that jailbreaking was illegal which is not
exactly true.
You see, the act of jailbreaking itself is completely legal at least in the US thanks
to section 1201 of the Digital Millennium Copyright Act.
However, what you do with the jailbreak may be illegal.
For example, if you’re pirating apps, movies, or music, then you’re clearly breaking copyright
laws.
But, if you’re simply downloading free tweaks from Cydia’s app store, you’re not breaking
any laws in the US.
Aside from the illegality argument, Apple also made it clear the jailbreaking may lead
to significantly more crashes and a much less stable operating system.
Now this is completely true.
I think everyone who has jailbroken in the past is very familiar with the infinite reboot
loop.
Not to mention, all of the random crashes that occur when you’re just using the device
normally.
Apple’s warnings weren’t that effective though.
Most people that were jailbreaking were well aware of all the risks, and Apple’s warnings
weren’t gonna stop them.
Something that would prove extremely effective though was making jailbreaking obsolete.
Instead of trying to dissuade people from jailbreaking, Apple eventually just decided
to give people what they wanted without having to jailbreak.
For example, they introduced dark mode, they redesigned notifications, they finally gave
us widgets, they created a low power mode, they enabled biometric authentication, and
so on and so forth.
Honestly, I don’t know why they didn’t just do this from day 1, but they eventually
got there.
And as Apple natively implemented one jailbreak feature after another, the motivation to jailbreak
quickly dissipated.
Jay tried to hold onto Cydia for as long as possible, but as Cydia became a money losing
business, Jay decided to call it with Cydia in December of 2018.
He announced that Cydia would be shutting down their purchasing mechanism which made
it signficnatly harder for developers to make money from their tweaks.
And consequently, the entire jailbreaking community moved over to a new jailbroken app
store called Sileo.
And that marked the end of Cydia.
JAY FREEMAN TODAY: In terms of what Jay is doing today, he did
try to sue Apple for creating a monopoly with their app store, but as you would guess, this
hasn’t really gone anywhere.
So, Jay decided to return to something that’s he’s familiar with which is UC Santa Barbara.
In January of 2016, Jay announced that he’s running for the Santa Barbara county board
of supervisors.
Unfortunately, he lost this election.
However, he would turn around and run for the Board of Directors at the Isla Vista Community
Services District, and he would win and he’s been serving in this position eversince.
In terms of Jay’s views on jailbreaking, he still believes in the fundamental principles
behind jailbreaking.
For example, he believes that all software should be built with screws so that they can
be disassembled.
And the jailbreaking community has made insane progress in this realm.
In fact, a jailbreak called checkm8 can apparently permanently jailbreak a subset of Apple devices
and there’s nothing Apple can do about it.
But, despite this progress, there’s no question that jailbreaking as a whole has been on a
downtrend for years now.
I mean, just take a look at this google trends graph.
Interest in jailbreaking has literally fallen 20 fold since 2013.
And at the end of the day, it just comes down to one question: What do you get in the end
by jailbreaking?
Jay Freeman says “It used to be that you got killer features that almost were the reason
you owned the phone.
And now you get a small minor modification.”
And with time, this is likely only going to get worse which will eventually make jailbreaking
completely obsolete.
With that being said though, jailbreaking will always remain a fond memory of the early
days of the iPhone and Jay Freeman will always be the godfather of jailbreaking.
Did you guys jailbreak your Apple devices?
Comment that down below.
Also, drop a like to pay your respects to Cydia.
And of course, consider checking out our international channels to watch our videos in other languages
and consider subscribing to see more questions logically answered.