Alphabet’s controversial chief legal officer David Drummond is leaving, saying he has decided to retire

The changing of the guard at Alphabet continues. Roughly one month after Google founders Larry Page and Sergey Brin announced they’d be stepping down as the CEO and president of the search giant’s parent company, one of their top lieutenants, Alphabet’s chief legal officer, David Drummond, told employees that he is also leaving the company.

In a memo shared with Bloomberg and reprinted below, Drummond said that “with Larry and Sergey now leaving their executive roles at Alphabet” and the company “entering an exciting new phase,” he is, after “careful consideration,” retiring “to make way for the next generation of leaders.”

His departure can’t surprise many in Silicon Valley. In November, Alphabet’s board of directors opened an investigation into how executives at the company have handled misconduct claims, forming both an independent subcommittee and hiring a law firm to look into the issues. Presumably, much of their attention was focused on Drummond, whose long-ago extramarital affair with one employee with whom he shares a child first surfaced in a story by The Information in 2017, and who more recently married another employee from Google’s legal department.

Though Alphabet has long supported Drummond — he helped incorporate the company when it was founded in 1998 and remained one of its top executives — the corporate giant came under pressure to do something after Drummond’s earlier affair began to garner unwanted attention. Specifically, the former employee with whom he shares a child, Jennifer Blakely, published a post on Medium last summer in which she described Drummond as a serial philanderer who left his wife for her, then left her and the son that he fathered with her for another now-former Google employee.

Blakely also claimed Drummond had had “an affair with his ‘personal assistant’ who he moved into one of his new homes.”

One day later, Drummond issued a statement of his own, acknowledging his relationship with Blakely and their “difficult break-up 10 years ago.” He went on to state that, “Other than Jennifer, I never started a relationship with anyone else who was working at Google or Alphabet. Any suggestion otherwise is simply untrue.”

Days after issuing the statement, Drummond married a Google employee he’d been dating.

Not everyone was supportive of Drummond inside the company. In addition to employees who’ve pushed back against the company’s culture in recent years, Bill Maris — who founded Google’s venture arm and as the unit’s CEO reported directly to Drummond — had a strained relationship with him, Maris says.

Specifically, Maris tells Axios that Drummond is why he left GV back in 2016. “I had been asked in the past why I left . . . David Drummond is the reason I left Google. I simply could not work with him any longer.  It’s that simple. We have very, very different ideas about how to treat people, and this was a long time coming.”

Drummond made a substantial fortune throughout the course of his career with Google, then Alphabet. He was paid $47 million last year. According to stock filings tracked by CNBC, he also sold $77 million worth of stock earlier this month, following sales of more than $70 million in November and again in December, just before Page and Brin said they were departing their roles.

Roughly six years ago, Brin also reportedly dated a Google employee while still married to his first wife, 23andMe founder Anne Wojcicki.

Both Page and Brin remain on the board of Alphabet. Drummond’s last day with the company will be January 31.

Drummond’s note to employees follows:

More than 20 years ago, Larry Page and Sergey Brin first asked me to help them with their unincorporated startup. Of course, that startup would grow to include more than 100,000 employees and make a positive impact on the lives of people around the world. From the beginning, I felt privileged to work with Larry and Sergey to realize their commitment to making information more universally accessible and useful, and was thrilled to join Google full-time in 2002.

With Larry and Sergey now leaving their executive roles at Alphabet, the company is entering an exciting new phase, and I believe that it’s also the right time for me to make way for the next generation of leaders. As a result, after careful consideration, I have decided to retire at the end of this month.

As I do so, I’d like to thank everyone with whom I’ve had the privilege to work so closely over the past two decades. Whether we were fighting alongside others around the globe to protect and expand freedom of expression; pressing to make sure copyright law continued to foster openness and creativity; designing an unconventional but dynamic corporate structure that has served Google so well; putting together industry-changing acquisitions that served as the foundation for some of Google’s most popular products; creating and evolving the rules that protect our users; or establishing start-up models to help unleash the potential of our amazing Other Bets: I have always relished the opportunity to work with such talented colleagues.

In particular, I have loved building and being a part of the legal team: your dedication, drive and leadership in helping digital innovation flourish has been amazing to behold. I have also been energized and deeply impressed by my time with the corporate development, public policy, trust and safety and communications teams, as well as the folks at GV, Capital G and Jigsaw. These groups’ relentless creativity and herculean efforts to further Google’s ambitious mission have been beyond inspiring. I’d also like to thank BGN and all of the company’s employee resource groups, whose tireless efforts continue to make the company better.

I know this company is in the best of hands, and I am excited for what the future holds for Google, for Alphabet and for me. But, as I move on, I’d like to thank Larry and Sergey and each and every one of you for providing me with the most engaging, challenging and rewarding professional environment that anyone could hope for. I am deeply grateful.