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Oakland man’s Instagram posts come back to haunt him in federal court

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OAKLAND — Federal prosecutors here have filed gun possession charges against an East Bay man who is also suspected of involvement in a robbery crew made up of gang members, court records show.

Ray Gilbert, 25, was charged last month with being a felon in possession of a firearm found during a search of an Oakland residence where he and two others lived, court records show. The search was predated by a police investigation that centered on Gilbert’s own Instagram posts, mostly selfies of him possessing guns, flashing cash, and making threats towards a rival gang, according to federal prosecutors.

Gilbert also faces charges in four separate prosecutions in Alameda County — he is charged with two parole violations, retail theft for allegedly stealing thousands in merchandise East Bay stores, and firearms possession, court records show. Prosecutors have cited his suspected involvement in a “Case Gang robbery crew” that was active throughout 2023 as a reason to keep him jailed while the federal case is pending, but he hasn’t been charged in connection with the armed robbery spree.

A judge is set to rule on the motion to jail Gilbert at a Sept. 12 court hearing.

A review of investigations tied to Gilbert indicate that he’s been a major law enforcement target in violent crime investigations since at least 2020. In each instance, though, police were unable to find enough evidence to justify charging Gilbert or his associates with the more serious charges.

Prosecutors describe Gilbert as “at least” an associate of the Case Gang, an Oakland gang that has had a bloody, decades-long rivalry with another gang known as Stubby/ENT. Oakland police investigators started monitoring Gilbert’s Instagram, @Stains—3k0, and took screenshots of pictures and videos that were later used to justify the search of his home, according to court records.

Police were also investigating Gilbert for suspected involvement robberies dating back to at least March, when a man who won money at the Livermore casino was followed home and robbed, according to federal prosecutors. He is also one of four men suspected in a string of armed robberies in Oakland in July and August, along with another man who was recently charged with possessing a firearm at an illegal casino in Oakland.

But authorities say that Gilbert has been a major law enforcement target since at least 2020, when his phone was wiretapped — along with six other suspects Case Gang affiliates — as part of a joint police investigation into shootings in Oakland and San Pablo, authorities say. No charges were ever filed against Gilbert or the five others, and the shooting investigations remain open.

Both gangs tied up in major Antioch police scandal 

Both the Case and Stubby/ENT gangs have been the subject of major federal and state investigations for years that have now been called into question by alleged widespread police misconduct.

A 2021 task force investigation and wiretap that focused on both gangs, dubbed Operation Windstar, was disrupted when police discovered an Antioch officer allegedly called one of the wiretap targets and mislabeled the phone call as non pertinent. The officer, Timothy Manly-Williams, now faces federal and state charges, along with more than a dozen current and former Antioch and Pittsburg cops.

A murder case involving four alleged ENT members from March 2021 recently hit a major snag when it was revealed that multiple Antioch police officers who investigated the case were also sending racist texts and memes, including communications that specifically referenced some of the defendants.

Meanwhile, in Alameda County, prosecutors inexplicably dropped attempted murder charges against four suspected Case Gang members and associates who were investigated as part of Operation Windstar. The defendants, had been jailed since early 2021, and in March 2023, a judge held them all to answer on charges of attempted murder, multiple counts of assault, and gun possession.

But then, on April 20, 2023, an Alameda County prosecutor moved to dismiss the entire case, stating only that the move was being made “in the interests of justice,” without elaboration. Just three days earlier, though, Ali’s lawyer filed a motion for discovery that said Oakland police Det. Alexander Schmarzo admitted he’d worked closely with Antioch officers who were later implicated in the the racist texting scandal in order to identify the four men as shooting suspects.

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