The video is high quality, as might be expected of a surveillance camera in the penthouse bedroom of a high-tech princeling.

The footage was so clear that San Francisco police were able to determine that Gurbaksh Chahal punched and kicked his girlfriend 117 times in 30 minutes. He also smothered her with a pillow for 20 seconds.

“She stated she was unable to breathe,” San Francisco Police Officer Anh Nguyen testified at the preliminary hearing against Chahal, as reported in the San Francisco Chronicle. “She stated that he said, ‘I’m going to kill you’ four times. She stated she was in fear for her life.”

Chahal was charged with 47 felony counts in the Aug. 5, 2013, attack, including possession of a deadly weapon, the pillow.

And it seemed certain that 31-year-old Chahal was one Silicon Valley startup star for whom IPO would now stand for Initial Prison Offering.

Never mind that Chahal had become a figure of legend by selling his first digital ad startup, ClickAgent, for $40 million when he was just 18.

Never mind that Chahal sold his second digital ad startup, BlueLithium, for $300 million four years later.

Never mind that Chahal had been declared “America’s Most Eligible Bachelor” by the TV show Extra! and deemed one of the planet’s “richest and fittest guys” by Men’s Health magazine.

Never mind that Chahal had posed smiling beside President Barack Obama at a fundraiser just 10 months before the attack.

Never mind that Chahal now put his megabucks to work, hiring one of San Francisco’s very best defense lawyers, a former prosecutor and retired brigadier general named James Lassart.

Never mind that the girlfriend who had started it all with a call to 911 and who had told the police she had been afraid for her life suddenly ceased to cooperate with the authorities.

Never mind that Chahal had allegedly paid her as much as $4 million, as charged in a civil suit filed by a former employee.

Never mind that he arranged to pay another $1 million to a prominent political powerbroker who suggested he might be able to make the case “go away.”

The cops still had the video.

Until they didn’t.

Before Chahal even had to attempt a fix, a judge ruled that the video was inadmissible because the police had seized it improperly. The judge was not swayed by the prosecutor’s argument that the cops hadn’t had time to secure a warrant because a tech mogul could so easily erase the footage.

With no victim and no video, the district attorney’s office agreed to reduce the 47 felony charges to two misdemeanors. Chahal pleaded guilty with the understanding that he would get probation, along with 25 hours of community service and a $500 fine.

“A traffic ticket,” Chahal remarked online.

He sought to excuse himself and smear the woman by suggesting in a blog that he had only reacted as anyone might upon learning that his girlfriend had supposedly engaged in “unprotected sex for money with other people.”

“There is a difference between temper and domestic violence,” he contended.

That blog has since been taken down, but he had another called BeLimitless, which includes a “Relationships” section. He described himself as a “diehard entrepreneur. Love innovation & building amazing companies.”

That June, Chahal had not hesitated to call the police himself and complain that he was being harassed by an “obsessed female fan.” He said the fan—an accountant in South Carolina—had been sending him unsolicited emails in such a way as to “interfere with his personal and professional life.”

In the meantime, Chahal had agreed in his guilty plea to attend a 52-week domestic violence class. The course was not yet halfway done on Sept. 17, 2014, when police received another 911 call from his penthouse. Chahal’s new girlfriend—whom he’d met in Las Vegas while the first case was pending and who should not be confused with the supposedly harassing “female fan”—reported to the dispatcher that he had physically assaulted her in his penthouse.

“Same room, same bed, just no security camera that we know of,” says Beverly Upton, executive director of the San Francisco Domestic Violence Consortium.

Unfortunately, there was one more similarity between the two cases: this alleged victim also suddenly declined to cooperate with the investigation. She is said in court papers to have hopped a plane back to her native South Korea after Chahal allegedly threatened to turn her in for immigration fraud. The district attorney’s office again found itself without enough material to prosecute a criminal case.

But where a criminal case requires proof beyond a reasonable doubt, the district attorney’s office needed only a preponderance of the evidence to establish that Chahal had violated his probation when he allegedly assaulted a second woman.

In a brilliant move, the district attorney’s office asked the judge if the video from the first case could be admitted to establish that the second assault was essentially a repeat offense. The judge ruled that it could.

The prosecution also had a recording of the 911 call made by the second girlfriend. That and the video convinced the judge, who ruled on July 22 that Chahal had indeed violated his probation.

The sentencing is set for Aug. 12, three years and one week after Chahal assaulted his first girlfriend. The two misdemeanor counts to which he pleaded guilty each carry a one-year maximum, but the district attorney’s office had thought to arrange it so that the sentences would be served consecutively if Chahal violated his probation. Now he may be hit with two years, much less than he would have received if he had been convicted of the felonies, but two years more than he would have received otherwise.

Then again, the judge could conceivably allow Chahal once more to avoid incarceration, depending on what the probation report recommends.

In the meantime, The Wall Street Journal has found in court papers a remarkable email exchange between Chahal and a mogul on the board of his third digital ad startup, RadiumOne, back at the time of the first arrest.

The mogul was Steve Westly, who had scored big with eBay early on and hoped for another big score with RadiumOne’s Initial Public Offering. That hope was dimmed by the prospect of the firm’s founder and CEO facing an Initial Prison Offering.

Westly is a former California State Controller who had made a failed run for governor in 2006 and hoped to try again. He was pals with Willie Brown, a former mayor of San Francisco and onetime speaker of the California State Assembly. Westly, the Journal reported, emailed Chahal that Brown “believes he can help you.” Westly told Chahal that Brown was friendly with San Francisco District Attorney George Gascon and “may be able to ‘back him off.’”

At Westly’s suggestion, Chahal met with Brown. Chahal reported back to Westly in an email with the subject line “Willie Brown.” Chahal wrote, “Just met him. Wants $1 million if he can make this go away. Just gave him a $250K retainer. If you meet him tomorrow. Apply some pressure on him to make this go away in 2013.” Westly replied, “Wow. That’s pricey, but probably worth it if he can make it happen. I suspect he will pull out all the stops to get this done.”

But Gascon would not likely have been swayed even if he had been approached. Any such attempt ceased to be necessary when the judge threw out the video. Chahal was nonetheless forced from his position at RadiumOne, but he soon had a new digital ad startup, Gravity4. His senior employees there included a young Canadian named Yousef Khraibut, who subsequently filed a wrongful termination suit that describes Chahal as a CEO from hell itself.

“Chahal, fueled by a toxic cocktail of prescription drugs, party drugs, alcohol, and sycophants, subjected his associates and Gravity4 employees to daily abuse, humiliation, racist taunts, extortionate manipulation, tales of revenge, and threats of violence,” the suit, which was filed in a San Francisco federal court, alleges.

The suit continues, “Finally, when Khraibut dared to stand up to Chahal’s abuse, threats, and illegal behavior, Chahal repeatedly threatened Khraibut with violence, fired him, and hustled him out of the country, hounding him with continued threats, stalking, defamation, interference, and manipulation. Khraibut brings this action to vindicate his legal rights, and to stop Chahal from repeating these practices against other unknowing victims in the future.”

With regard to first assault, the suit claims, “Chahal told Khraibut that the woman had originally demanded $200,000, then increased her demand to one million after her family’s input, and finally to two million. Khraibut later learned that the amount of the ultimate payment was higher than two million dollars, possibly as much as four million dollars. It was clear in the context of Chahal’s discussions with Khraibut about these issues, that the victim had been paid at least in part to ‘be quiet’ and not cooperate with the criminal investigation.”

The suit claims Chahal also spoke to Khraibut about the effort to put in the unneeded fix with Willie Brown. The suit reports, “Chahal described a near-confrontation with Brown in the St. Regis hotel lobby in San Francisco while Chahal was with his bodyguard… Chahal boasted that he had forced Brown to give back much of the original retainer that Chahal had paid him.”

The suit further reports that after the judge ruled the video inadmissible, Chahal remained fearful of it “ever getting into the hands of the media or other adverse parties.” He did not explain why he would be so worried if he only hit the woman with a pillow in self-defense, as he had contended.

“Chahal’s story evolved to admitting that Chahal had struck his girlfriend with his hands, i.e. ‘just shook her and slapped her,’ but that he did not hurt her,” the suit says.

The suit also claims that Chahal remained concerned enough about a negative image that “Gravity4’s hiring efforts were focused in part on hiring women executives and employees to combat Chahal’s negative image in the wake of his domestic violence conviction.”

Even so, the suit alleges, “Gravity4’s female hiring efforts were colored by Chahal’s focus on women’s appearances during the hiring process. In one instance, Chahal researched a young, attractive female sales manager applicant by finding online photographs of her wearing a bikini, and then showing them to other male employees, including Khraibut, seeking their opinion on her breasts. When Khraibut protested via Skype chat that it ‘wasn’t right’ to be checking out a prospective hire’s bikini pictures, Chahal responded, ‘Research bro. Everything is online. I do this on every candidate.’”

The suit adds, “Chahal frequently referred to women in the workplace in both vulgar and derogatory terms. For example, during the hiring process, Chahal would refer to allowing an attractive woman to proceed in the interview process, as a ‘pussy pass.’”

As for his own gender, “Chahal would use the term ‘on PMS’ as a derogatory slur toward men executives, including Khraibut, who were having a difficult day.”

The suit says that Chahal called Khraibut a “terrorist” and was heard to use the N word regarding people of color. He also had opinions about Jewish people. “Chahal complained that Jews ran Silicon Valley and had conspired against him in business, and that if his last name had been ‘Zuckerberg,’ his former RadiumOne investors would have supported him,” the suit says.

Chahal’s own family was apparently not spared his scorn. The suit contends that he “ridiculed his immediate relatives as ‘ungrateful pieces of shit,’ and that they betrayed him, even after Chahal ‘made them all millionaires,’ because the relatives refused to support Chahal’s decision to publicly trash his former girlfriend and domestic violence victim.”

Then came the second assault case. Khraibut claims in the suit that Chahal texted him in the middle of the night, summoning him to the penthouse. Chahal was there with his bodyguard, Moepulou Alais, a bouncer whom he had also met in Las Vegas, the suit claims.

“Chahal instructed Khraibut to tell the police that Khraibut had been in the condominium during the alleged incident ” the suit says. “Khraibut was unwilling to state to authorities that he had been in the apartment at a time that he had not been.”

The suit adds, “Chahal was enraged that Khraibut refused to buttress Chahal’s alibi against [the woman’s] assault charges.”

The suit goes on, “When Khraibut dared to stand up to Chahal’s abuse, threats, and illegal behavior, Chahal repeatedly threatened Khraibut with violence, fired him, and hustled him out of the country, hounding him with continued threats, stalking, defamation, interference, and manipulation.”

The suit—filed in San Francisco federal court Sept. 28, 2015 and contested by Chahal, who is presently seeking to have it sent to arbitration over Khraibut’s objections—concludes, “Khraibut brings this action to vindicate his legal rights, and to stop Chahal from repeating these practices against other unknowing victims in the future.”

In the meantime, Westly was still talking about running for governor in 2018 despite his efforts on Chahal’s behalf, regarding which Beverly Upton notes, “That’s not helping him, that’s enabling him.”

“[Westly] was really helping himself,” Upton says, suggesting the mogul’s priority was the planned RadiumOne IPO.

That did not stop the Democratic Party from using Westly’s home for a fundraiser.

The invitation read:

The Democratic National CommitteeCordially invites you to a Brunch Reception with special guestBARACK OBAMATo support the Democratic Hope FundThursday, February 11, 2016The home of Steve WestlyAtherton, CA

The guests did not include Chahal, who was busy trying to avoid a long-delayed Initial Prison Offering. Chahal did not respond to a request for comment. Nor did Westly. Nor did Brown, who has insisted that his dealings with Chahal involved nothing unethical.

We will find out at the end of this week whether Chahal will end up behind bars, as it seemed so certain he would when the cops first seized that video.

The judge has ruled that the footage will remain sealed because the victim’s face is recognizable, as might be expected with a surveillance camera in the penthouse bedroom of a high-tech princeling.