Jay Freeman, a.k.a. “saurik,” took the stage at MyGreatFest, the world’s first jailbreak convention, to talk about his hugely successful jailbreak store known as Cydia. As the father of Cydia and the most prominent figure in the jailbreaking community, Freeman shared insight into the history and future of Cydia and jailbreaking.

We’ve collected some highlights and quotes from Freeman’s talk at MyGreatFest…

First off, it’s interesting to note that Freeman started coding in the 2nd grade. Since then, he has created a jailbreak store used by millions of jailbreakers around the world.

Although Freeman noted that he hasn’t been explicitly approached by Apple, he did describe receiving a “veiled job offer” once from an Apple employee. He believes that Apple would rather pretend that he doesn’t exist, and he doesn’t plan on leaving the jailbreak community anytime soon.

The State of Jailbreaking and Cydia

Freeman said during his talk that between 6-12% of all iDevices are jailbroken at any given time. He explained that the percentage fluctuates depending on when Apple releases a new version of iOS. When a new iOS firmware gets released, he said that the number drops down to about 6%. This makes sense if you think about most people wanting to upgrade and try the new features that Apple implements in a new iOS version.

Freeman does not work on jailbreaks himself, although he did note that he tinkers with some side projects for fun. His main job is the upkeep of Cydia. He leaves the actual jailbreaking to groups like the Chronic Dev Team. He is, however, a member of the famous Dev Team, alongside other prominent figures like MuscleNerd. He described the Dev Team as a “very private IRC channel where guys hang out.”

When asked about how many apps were actually in Cydia, Freeman responded with “about 4.” Freeman sees Cydia as a place for things that don’t belong in the App Store, like tweaks and low-level extensions. Freeman took the time to explain what the word “Cydia” actually meant, but you can refer to our explanation for more information on that topic.

Freeman said that Cydia can be a place for the distribution of rejected App Store apps. He remained ambiguous, as he clearly wants to keep Cydia as a hub of tweaks and hacks that would never make it into the App Store in the first place. Cydia does welcome rejected App Store apps with open arms.

Update: Freeman has clarified his real point on this issue in the comments on this article. Here is what he had to say:

“I explained in my answer that Cydia’s default repositories are often forced to reject applications for the same reasons that Apple is forced to reject apps, and that if you have an app you want to list and it comes out that it was rejected by Apple you are going to get serious scrutiny: Cydia is /not/ a dumping ground for rejected apps, and it is incredibly irritating when people see “X rejected from the App Store” and immediately connect to “let’s get it into Cydia”… the content is often illegal in the US (and I provided an example, such as the large number of apps that get rejected for using photographs of public figures in dubious manners) or technically broken. Only in a very very very limited number of cases do you find Apple rejecting things for “illegitimate” reasons, and in those cases it is often a large company that competes with Apple (Google) which usually take their matters to court (or the FTC) rather than to Cydia. I did, however, state that you can always make a private repository with whatever you want in it, but then the question is invalid: it is like asking if you can bring your content to FireFox… Cydia is a web browser for package content, and there is no way that anyone can tell you what URLs you are or are not allowed to access.”

On multitasking in Cydia, Freeman made it clear that he is working on a solution. He is trying to find a way to make Cydia not run as root so that multitasking will work. When asked about the feature, he said, “I’ve got some ideas.”

What about Cydia for Mac? There were rumblings in the community awhile back about Freeman essentially jailbreaking the Mac. After the initial buzz, nothing has been heard for months about the project. Freeman shed some light on Cydia for Mac today at MyGreatFest.

Freeman said that, when he first brought up the idea of a Cydia for Mac, many people couldn’t understand why you would need to jailbreak the Mac in the first place. When Apple introduced OS X Lion, Freeman saw that Apple was continuing to make OS X more ‘sandboxed’ and closed. Due to the complexities in Lion, Freeman said that Cydia for Mac will be released “when it works.”

Freeman is against piracy. Only 1/70 people actually pay for Cydia tweaks, and it seriously cripples the community from growing and becoming stronger. However, Freeman did say that, “If you have a free and open system, piracy is going to occur.” When you jailbreak, you are given the ability to do whatever you want with your device — including pirate. Freeman said, “Once you open Pandora’s box, you can’t close part of it.”

Cydia is an open source project, so Freeman can’t edit or moderate the content that is distributed. Cydia could have a signature system like the App Store for authenticating legitimate users, but multiple jailbreak tools from multiple groups (Dev Team, Chronic Dev Team, etc.) make that impossible.

Instead, Freeman tries to convert pirates. He made the argument that, instead of someone spending hours upon hours trying to crack complicated DRM code, those hacking skills could be put to good use for the community. He noted that several prominent pirates have changed sides and are now working to make Cydia a better and more innovative place.

Freeman talked for a long time about how Cydia was a collaborative project that took many years to develop. He talked about interesting little tidbits, like the evolution of the Cydia icon and the people that helped create Cydia at the beginning of it all. His talk helped to remind us that jailbreaking is very much a community effort, and that the people behind the computer screens are what make jailbreaking so special.