Last week, the hacker who became famous as the first person to “jailbreak” an iPhone was booked and charged with felony marijuana possession, police in Sierra Blanca, Texas, told Above the Law. George Hotz was heading to the annual SXSW conference in Austin when he was arrested.

Hotz joins a star-studded list of people busted for pot at the infamous border patrol checkpoint in the small West Texas town.

Let’s learn more about Hotz, his brush with Texas justice, and the legally questionable drug-busting strategy employed by local law enforcement in Sierra Blanca…

Hotz, who also goes by “geohot” online, is a hacking phenom. In 2008, he jailbroke the iPhone by physically taking it apart. (In the years since, people have figured out ways to do it using just software.)

He made headlines again last year when he got involved in a public spat with PlayStation after jailbreaking the PS3. Sony filed a lawsuit against him that was eventually settled out of court. Sony’s lawsuit spawned retaliation from Anonymous.

Not that any of this has prevented the 22-year-old from starting a successful career in the technology world. He has worked with Google and, up until recently, as a software engineer at Facebook.

Hotz was on his way to give a talk at SXSW, when he had to pass through a border patrol checkpoint in Sierra Blanca. According to a source familiar with the case, Department of Homeland Security officers brought drug dogs to each car. When the dogs barked, Hotz (and his passengers) were pulled over for more searching.

Hotz has a medical marijuana license in California, where he lives, our source says. In the car’s glove box, Hotz apparently had 1/4 oz. of marijuana and chocolate edibles equivalent to less than 1/8 oz. of the drug.

The border agents allegedly said they would turn Hotz over to the local sheriff and he would get a citation. Not a big deal, right? But our source explains the local sheriff took the whole weight of the chocolate as the proper measure (as if the candy were made entirely of pot). Law enforcement then valued the “special” chocolate truffles at $800, instead of the $15 our source says Hotz paid for it.

An $800 pot truffle? Man, that would put you in a coma. A real coma, not a normal stoney-baloney zonk-out.

Hotz was booked for a felony and posted $1,500 bail.

Willie Nelson, actor Armie Hammer (who played the Winklevoss twins in The Social Network), and Snoop Dogg have all gotten in trouble at the same checkpoint under similar circumstances.

Hang on a sec, [pulls out iPhone] Siri, warn me when I roll into West Texas.

We reached out to Hotz, but he has not responded. If he does, we will update with any comments he might have.

Now, regardless of your opinion about marijuana regulations, our source (who is also an attorney) raises some interesting questions about the broader constitutionality of this border patrol checkpoint:

The whole setup is nominally for some non-narcotics purpose, but in spirit it all looks like it violates Indianapolis v. Edmond. If they aren’t pulling the cars over to check ID or anything like that UNLESS there is a dog sniff, how can they say the purpose of the roadblock isn’t to check for narcotics (impermissible under Edmond)?

It’s an interesting question. A Google search for Sierra Blanca turns up dozens of news articles about drug arrests at the border checkpoint. Defending drug arrests at the checkpoint is even an entire area of law practice for some attorneys.

This is what the Supreme Court had to say in Edmond:

Because the primary purpose of the Indianapolis narcotics checkpoint program is to uncover evidence of ordinary criminal wrongdoing, the program contravenes the Fourth Amendment…. We cannot sanction stops justified only by the generalized and ever-present possibility that interrogation and inspection may reveal that any given motorist has committed some crime.

Obviously, I cannot speak for every arrest made at the Sierra Blanca checkpoint. But the spot clearly has a reputation for domestic drug arrests, not immigration cases. And that’s what the Supreme Court was worried about.

But if you haven’t actually left the country, can you still be subject to a “border” search? The only possible justification might be that this “border” search should be subject to relaxed constitutional standards.

But that would only apply if Sierra Blanca were the “functional equivalent of a border.” And courts have wrangled for years over that question. Currently, the answer appears to be no.

Readers, what you think about all this? Am I just a hippie left-coast liberal? Or is this a serious criminal justice concern?