“I want to wish Andy all the best with what’s next,” Larry Page, Google’s chief executive then, said in a public statement. “With Android he created something truly remarkable — with a billion-plus happy users.”
What Google did not make public was that an employee had accused Mr. Rubin of sexual misconduct. The woman, with whom Mr. Rubin had been having an extramarital relationship, said he coerced her into performing oral sex in a hotel room in 2013, according to two company executives with knowledge of the episode. Google investigated and concluded her claim was credible, said the people, who spoke on the condition that they not be named, citing confidentiality agreements. Mr. Rubin was notified, they said, and Mr. Page asked for his resignation.
Google could have fired Mr. Rubin and paid him little to nothing on the way out. Instead, the company handed him a $90 million exit package, paid in installments of about $2 million a month for four years, said two people with knowledge of the terms. The last payment is scheduled for next month.
Mr. Rubin was one of three executives that Google protected over the past decade after they were accused of sexual misconduct. In two instances, it ousted senior executives, but softened the blow by paying them millions of dollars as they departed, even though it had no legal obligation to do so. In a third, the executive remained in a highly compensated post at the company. Each time Google stayed silent about the accusations against the men.
The New York Times obtained corporate and court documents and spoke to more than three dozen current and former Google executives and employees about the episodes, including some people directly involved in handling them. Most asked to remain anonymous because they were bound by confidentiality agreements or feared retribution for speaking out.
The transgressions varied in severity. Mr. Rubin’s case stood out for how much Google paid him and its silence on the circumstances of his departure. After Mr. Rubin left, the company invested millions of dollars in his next venture.
Sam Singer, a spokesman for Mr. Rubin, disputed that the technologist had been told of any misconduct at Google and said he left the company of his own accord.
“The New York Times story contains numerous inaccuracies about my employment at Google and wild exaggerations about my compensation,” Mr. Rubin said in a statement after the publication of this article. “Specifically, I never coerced a woman to have sex in a hotel room. These false allegations are part of a smear campaign by my ex-wife to disparage me during a divorce and custody battle.”
Mr. Rubin’s exit from Google after an inappropriate relationship was previously reported, but the nature of the accusation and the financial terms have not been disclosed.
In settling on terms favorable to two of the men, Google protected its own interests. The company avoided messy and costly legal fights, and kept them from working for rivals as part of the separation agreements.
When asked about Mr. Rubin and the other cases, Eileen Naughton, Google’s vice president for people operations, said in a statement that the company takes harassment seriously and reviews every complaint.
“We investigate and take action, including termination,” she said. “In recent years, we’ve taken a particularly hard line on inappropriate conduct by people in positions of authority. We’re working hard to keep improving how we handle this type of behavior.”
After publication of this article, Sundar Pichai, Google’s chief executive, and Ms. Naughton wrote in an email to employees that the company had fired 48 people for sexual harassment over the last two years and that none of them received an exit package.
“We are committed to ensuring that Google is a workplace where you can feel safe to do your best work, and where there are serious consequences for anyone who behaves inappropriately,” Mr. Pichai and Ms. Naughton wrote.
Some within Google said that was not enough.
“When Google covers up harassment and passes the trash, it contributes to an environment where people don’t feel safe reporting misconduct,” said Liz Fong-Jones, a Google engineer for more than a decade and an activist on workplace issues. “They suspect that nothing will happen or, worse, that the men will be paid and the women will be pushed aside.”
‘I Was the Liability’
Google, founded in 1998 by Mr. Page and Sergey Brin when they were Stanford University graduate students, fostered a permissive workplace culture from the start.
In Silicon Valley, it is widely known that Mr. Page had dated Marissa Mayer, one of the company’s first engineers who later became chief executive of Yahoo. (Both were single.) Eric Schmidt, Google’s former chief executive, once retained a mistress to work as a company consultant, according to four people with knowledge of the relationship. And Mr. Brin, who along with Mr. Page owns the majority of voting shares in Google’s parent, Alphabet, had a consensual extramarital affair with an employee in 2014, said three employees with knowledge of the relationship.
David C. Drummond, who joined as general counsel in 2002, had an extramarital relationship with Jennifer Blakely, a senior contract manager in the legal department who reported to one of his deputies, she and other Google employees said. They began dating in 2004, discussed having children and had a son in 2007, after which Mr. Drummond disclosed their relationship to the company, she said.
Google then took action. Ms. Blakely said Stacy Sullivan, then the head of human resources and now chief culture officer, told her that Google discouraged managers from having relationships with subordinates.
“One of us would have to leave the legal department,” Ms. Blakely said. “It was clear it would not be David.”
Since the affair, Mr. Drummond’s career has flourished. He is now Alphabet’s chief legal officer and chairman of CapitalG, Google’s venture capital fund. He has reaped about $190 million from stock options and awards since 2011 and could make more than $200 million on other options and equity awards, according to company filings.
Ms. Blakely was transferred to sales in 2007 and left Google a year later. The company asked her to sign paperwork saying she had departed voluntarily. She said she “signed waivers, releases and whatever else they wanted.”
In late 2008, she said, Mr. Drummond left her. They later fought a custody battle for their son, she said, which she won.
How Mr. Drummond, 55, was treated “amplifies the message that for a select few, there are no consequences,” said Ms. Blakely, 54. “Google felt like I was the liability.”
Google’s sexual harassment policy states that violators may be terminated — but it was flexible in how it enforced the rules.
In 2013, Richard DeVaul, a director at Google X, the company’s research and development arm, interviewed Star Simpson, a hardware engineer. During the job interview, she said he told her that he and his wife were “polyamorous,” a word often used to describe an open marriage. She said he invited her to Burning Man, an annual festival in the Nevada desert, the following week.
Ms. Simpson went with her mother and said she thought it was an opportunity to talk to Mr. DeVaul about the job. She said she brought conservative clothes suitable for a professional meeting.
At Mr. DeVaul’s encampment, Ms. Simpson said, he asked her to remove her shirt and offered a back rub. She said she refused. When he insisted, she said she relented to a neck rub.
“I didn’t have enough spine or backbone to shut that down as a 24-year-old,” said Ms. Simpson, now 30.
A few weeks later, Google told her she did not get the job, without explaining why.
She waited two years to report the episode to Google after she said she wrestled with talking about it. A human resources official later told her that her account was “more likely than not” true and that “appropriate action” was taken. She said the official asked her to stay quiet about what had happened, which she did — until Mr. DeVaul’s public profile began rising in articles in The New York Times and The Atlantic.
“We would never tell a complainant to stay quiet,” Chelsea Bailey, the head of human resources at X, said in a statement, adding that officials investigated and “took appropriate corrective action.” She declined to say what that was, citing employee confidentiality.
In a statement, Mr. DeVaul apologized for an “error of judgment.” He said X decided not to hire Ms. Simpson before she went to Burning Man and that he did not realize she had not been informed.
In another harassment case, Google paid Amit Singhal, a senior vice president who headed search, millions of dollars on the way out.
In 2015, an employee said Mr. Singhal groped her at a boozy off-site event attended by dozens of colleagues, said three people who were briefed on the incident. Google investigated and found that Mr. Singhal was inebriated and there were no witnesses, they said.
Google found her claim credible, they said. The company did not fire Mr. Singhal, but accepted his resignation and negotiated an exit package that paid him millions and prevented him from working for a competitor, said the people.
In a blog post in February 2016, Mr. Singhal said he wanted to focus more on philanthropy and his family.
With Google silent about the circumstances of Mr. Singhal’s departure, he found another lucrative job. Less than a year later, he became head of engineering at the ride-hailing company Uber. Weeks later, the technology news website Recode reported that Mr. Singhal had left Google after a misconduct accusation. Uber dismissed Mr. Singhal for not disclosing the inquiry.
Uber and Mr. Singhal declined to comment. In a statement last year, he said that “harassment is unacceptable in any setting” and that he had not engaged in any such behavior.
The $350 Million Man
Mr. Rubin joined Google in 2005 when it acquired his start-up, Android, for $50 million. Over the next few years, he helped build Android — the software now used in 80 percent of the world’s smartphones — into a huge success.
Search had positioned Google as a dominant player on desktop computers, but Android extended its reach and put Google’s maps, email and web browser on devices that people carry every day. The ads and mobile apps running on Android also generated tens of billions of dollars in profit.
That success gave Mr. Rubin more latitude than most Google executives, said four people who worked with him.
Mr. Rubin often berated subordinates as stupid or incompetent, they said. Google did little to curb that behavior. It took action only when security staff found bondage sex videos on Mr. Rubin’s work computer, said three former and current Google executives briefed on the incident. That year, the company docked his bonus, they said.
Mr. Singer, the spokesman for Mr. Rubin, said the executive “is known to be transparent and forthcoming with his feedback.” He said Mr. Rubin never called anyone incompetent.
Mr. Rubin, 55, who met his wife at Google, also dated other women at the company while married, said four people who worked with him. In 2011, he had a consensual relationship with a woman on the Android team who did not report to him, they said. They said Google’s human resources department was not informed, despite rules requiring disclosure when managers date someone who directly or indirectly reports to them.
In a civil suit filed this month by Mr. Rubin’s ex-wife, Rie Rubin, she claimed he had multiple “ownership relationships” with other women during their marriage, paying hundreds of thousands of dollars to them. The couple were divorced in August.
The suit included a screenshot of an August 2015 email Mr. Rubin sent to one woman. “You will be happy being taken care of,” he wrote. “Being owned is kinda like you are my property, and I can loan you to other people.”
In 2011, Mr. Rubin was appointed a Google senior vice president and started receiving about $20 million a year in salary, bonus and stock-based compensation, said two former Google executives with knowledge of the terms. In 2012, Google also lent Mr. Rubin $14 million to buy a beach estate in Japan. The loan was offered at below 1 percent interest, said people briefed on the transaction.
When Google combined management of Android with its Chrome division in 2013, Mr. Rubin lost a power struggle to Mr. Pichai, Google’s current chief executive.
He remained highly valued. That year, Google offered Mr. Rubin a one-time bonus of $40 million in stock and an additional $72 million of stock over the next two years, said two people with knowledge of the terms.
Around that time, Mr. Rubin was casually seeing another woman he knew from Android, according to two company executives briefed on the relationship. The two had started dating in 2012 when he was still leading the division, these people said.
By 2013, she had cooled on him and wanted to break things off but worried it would affect her career, said the people. That March, she agreed to meet him at a hotel, where she said he pressured her into oral sex, they said. The incident ended the relationship.
The woman waited until 2014 before filing a complaint to Google’s human resources department and telling officials about the relationship, the people said. Google began an investigation.
In September 2014, a few weeks into the inquiry, Google’s board awarded Mr. Rubin a stock grant worth $150 million, to be paid out over several years, said three people briefed on the decision. It was an unusually generous sum, even by Google’s standards.
Mr. Page typically recommends how much senior executives are paid, said three former Google executives. Over the years, Mr. Page had told people he felt Mr. Rubin was never properly compensated for his contribution to Android, two people who spoke to him said.
The $150 million stock grant to Mr. Rubin was approved by the Google board’s leadership development and compensation committee — composed of Paul Otellini, Intel’s former chief executive who died in 2017, and two of Google’s earliest investors, John Doerr of the venture capital firm Kleiner Perkins and Ram Shriram of the venture firm Sherpalo Ventures.
It is unclear if Mr. Page or the board knew of the investigation into the harassment complaint when Google approved the $150 million grant for Mr. Rubin. Mr. Page, 45, did not respond to a request for a comment; Mr. Doerr and Mr. Shriram declined to comment.
Google’s inquiry ultimately found the complaint against Mr. Rubin credible, said the two company executives familiar with the incident. Mr. Rubin denied the accusation, but it became clear that — at the very least — the relationship was inappropriate, they said. Mr. Page decided Mr. Rubin should leave, they said.
The $150 million stock grant gave Mr. Rubin an enormous bargaining chip when he started negotiating his exit package about a month later. That is because an executive’s stock compensation — and how much of it they would leave behind — is often taken into consideration during settlement talks.
When Google fires lower-level employees, it typically marches them out immediately and pays little, if any, severance. But for senior executives, Google weighs other factors, said former executives. A wrongful termination lawsuit could mean unwanted media attention for Google and the victims of a misconduct case, with a loss resulting in significant damages.
In the end, Google paid Mr. Rubin $90 million, said two people with knowledge of the terms. The package was structured so that he received $2.5 million a month for the first two years and $1.25 million a month for the following two years.
A provision in the separation agreement precluded Mr. Rubin from working for rivals or disparaging Google publicly, they said. Google also delayed repayment of the $14 million loan.
The company then went out of its way to make Mr. Rubin’s departure seem amicable, including Mr. Page’s public statement of gratitude.
Afterward, Google invested in Playground Global, a venture firm Mr. Rubin started six months after leaving the company. Playground has raised $800 million. He also founded Essential, a maker of Android smartphones.
Last November, after the technology news site The Information reported that Google had investigated Mr. Rubin for an inappropriate relationship, he took a leave of absence from Essential. He has since returned to run it and is busy with speaking engagements and investments.
Mr. Rubin’s wealth, fueled by Google, has increased by 35 times in less than a decade. According to his ex-wife’s suit, his net worth is now about $350 million, up from $10 million in 2009.
Claire Cain Miller contributed reporting from Portland, Ore. Doris Burke contributed research.