TL;DR: Sam Bankman-Fried's lawyers have to be pulling their hair out by now. On more than one occasion, the prosecution caught the alleged swindler trying to influence witnesses. In his latest effort, SBF supposedly leaked select portions of his ex-girlfriend and former Alameda CEO Caroline Ellison's private thoughts stored on a shared Google Drive. Prosecutors have asked the judge for an injunction to forbid him or anyone else from disseminating any more information related to the case.

On Thursday, the New York Times published an article revealing portions of Sam Bankman-Fried's co-conspirator and ex-girlfriend Caroline Ellison's private diary. Although the NYT did not cite a source, US prosecutors alleged that SBF was the one who leaked the journal excerpts in a bid to discredit Ellison, who prosecutors scheduled to testify in his hearing starting October 2.

Assistant US Attorney (AUSA) Danielle Sassoon filed a motion with US District Judge Lewis Kaplan to forbid Bankman-Fried or any other witness in the case from "extrajudicial statements," colloquially known as a "gag order." Sassoon says the injunction is necessary to ensure a fair trial by an impartial jury.

The Justice Department believes that SBF intentionally leaked cherry-picked portions of Ellison's private writings, kept on a shared Google Drive and were not part of discovery. Prosecutors claim SBF wanted to portray her as a "jilted lover who perpetrated these crimes alone." The DoJ also claims that the leak had a secondary effect of influencing witnesses and jurors. Sassoon says that witnesses have already indicated that they are worried about testifying for fear of being publically humiliated.

"These witness concerns will only be heightened if witnesses are made to fear that a consequence of testifying against the defendant may include personal humiliation and efforts to discredit their reputation that go beyond what the rules of evidence might permit during cross-examination," said the AUSA in her filing. "In addition to tainting the jury pool, the effect, if not the intent, of the defendant's conduct is not only to harass Ellison but also to deter other potential trial witnesses from testifying."

The excepts revealed by the NYT article were not particularly damning for Ellison, who was serving as CEO of Alameda Research at the time of the FTX crypto exchange collapse. She expressed feeling unhappy and overwhelmed in a position she didn't feel qualified for.

"Running Alameda doesn't feel like something I'm that comparatively advantaged at or well suited to do," she wrote.

The piece also quoted entries addressed directly to SBF during their off-and-on romantic relationship. However, no snippets explicitly or implicitly indicate that she acted alone or happily complied with SBF's instructions to misuse company funds. On the contrary, Ellison expressed relief after hearing that FTX collapsed.

"I just had an increasing dread of this day that was weighing on me," Ellison wrote in an entry directed at SBF, which was previously revealed in discovery. "Now that it's actually happening, it just feels great to get it over with."

The document leak is not the first time Bankman-Fried has allegedly attempted to tamper with witnesses. In February, Judge Kaplan denied a motion to allow SBF to use messaging apps like Zoom, WhatsApp, FaceTime, or standard text messaging because he had been caught the month prior messaging witnesses with incriminating evidence against him via the Signal app, asking them to "reconnect" with him so they could "vet things with each other."