Back in June, the city voted to make it illegal for people to encourage sideshows and street racing on social media.
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Court documents name the defendants and the Instagram accounts believed to be owned by them.
In court on Friday, the focus was on the men's roles in encouraging sideshows through online posts.
Documents point to @sj_takeovers on Instagram, and allege the man behind the account had already been cited a number of times for crimes related to sideshow activity.
One account read, "He continues nonetheless to engage in the organizing and promotion of these events on social media and the internet."
"They've also instructed people, not just how to get there, but what to do when they get there," Legal analyst Steven Clark told ABC7 News. "And I think that's where the line has been crossed here."
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Clark is a former prosecutor and criminal lawyer. He explained, the city's law which criminalizes the promotion of sideshows and street races on social media, raises questions about free speech rights.
"The city's approach goes into some very questionable constitutional issues. For example, what the city is saying is, 'We want to restrain free speech before you've made it,'" he said. "So, I think the court is going to have a lot of problems with what the city is trying to do here, by basically quelling free speech before it occurs."
However, he understands this dangerous behavior must be addressed.
"Where is the line drawn here, between legitimate social media postings and your right to assemble and speak freely about an event," Clark questioned. "And where do you cross the line into dangerous activities and criminal behavior? Because essentially, what the city could also do is go after these guys criminally by saying you're aiding and abetting a criminal activity."
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Clark said social media today, allows people to instantly communicate with large groups of followers-- which makes it even more difficult for law enforcement.
"In the past, you would have had to put flyers and posters up to advertising event. Now you can do it in seconds and you can change direction, you can change locations very quickly," he elaborated.
Court documents addressed illegal activity seen in just one night: "Over the next three hours, San Jose Police responded to sideshow activities at four more locations corresponding to the addresses posted by sj_takeovers."
The account has nearly 15,000 followers.
"There's a spillover effect, not just for the participants in the slideshow, but the people who are around it," Clark told ABC7 News. "And the people who live in these communities and also the police trying to enforce the law."
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Dating back to December 2020, court documents show sj_takeovers posted "meet up" locations which often attracted more than 100 cars.
Documents say the illegal activity grew even more reckless as, "Responding officers heard gunshots," "Saw fireworks," and reported spectators, "Threw rocks at police vehicles."
"Certainly, towing their vehicles away, large fines- that could be a deterrent. But when you're approaching it from this point, you're almost making it more exciting to see that you can outrun the police when you're coming up with these sideshows," Clark added.
He continued, "At the same time, they're trying to prevent crime. In some ways, they're making it more enticing for the young people to participate because they want to be involved in these underground activities."
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If the city prevails, there is a list of penalties, fees defendants will have to pay.
ABC7 News reached out to the person identified by SJPD as the man behind the sj_takeovers account, but did not hear back. We've also reached out to the social media user through direct message and received no response.
ABC7 News reached out to the City of San Jose and its City Attorney's Office, but did not hear back on Friday.
This story will be updated to reflect any response received.