Microsoft execs told Bill Gates to stop sending flirty emails to midlevel female employee in 2008

REVEALED: Married Bill Gates was told by Microsoft’s top lawyer to stop sending flirty and ‘inappropriate’ emails to a mid-level female employee when he was CEO a decade ago

Bill Gates, who was CEO of Microsoft in 2008, was still married to Melinda GatesThat year, Microsoft executives found emails from Gates to a female employee Two top executives – Brad Smith and Lisa Brummel – held a meeting with GatesGates was told the flirtatious emails were inappropriate and he needed to stop Company spokesperson said emails were ‘flirtatious’ but ‘not overly sexual’  Microsoft’s board decided not to take any further action against Gates In 1992, board was told of affair Gates had with a top female Microsoft executive In May, Melinda Gates filed for divorce, saying union was ‘irretrievably broken’ Around that time, stories of Bill Gates’ pursuit of women began to emergeLast year, he quit Microsoft board after word leaked of affair with staffer in 2002 It was also learned that Gates asked out two employees while married to MelindaOne woman worked at Microsoft and the other worked at couple’s foundationBill and Melinda’s divorce finalized in August after Washington judge signed off Ex-couple seen over weekend walking daughter Jennifer, 25, down the aisle 



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Ex-Microsoft boss Bill Gates was reportedly told by two top executives at the firm to stop sending flirtatious emails to a female employee he had propositioned while he was CEO and married to Melinda Gates more than a decade ago. 

The revelation comes just months after Gates’ wife filed for divorce, claiming that the marriage was ‘irretrievably broken.’ The divorce was finalized in August.

Despite the acrimonious end to their marriage, the former couple reunited over the weekend in Westchester County, New York for the wedding of their oldest daughter, 25-year-old Jennifer Gates. Jennifer Gates wed 30-year-old Egyptian equestrian Nayel Nasser in front of 300 guests at her 142-acre estate in North Salem, New York.

The 2008 emails from Gates were sent to a midlevel employee at the software giant. They were later discovered by Microsoft executives.

Gates was summoned to a meeting by the company’s top lawyer at the time, Brad Smith, and Lisa Brummel, the firm’s most senior human resources executive.

During the meeting, Smith and Brummel told Gates that the emails were inappropriate and that he needed to stop, according to The Wall Street Journal.

Ex-Microsoft boss Bill Gates (seen right with then-wife Melinda Gates in 2010) was told by two top executives at the firm to stop sending flirtatious emails to a female employee he had propositioned while he was CEO and married to Melinda Gates more than a decade ago, it has been reported

Brad Smith (left), who was Microsoft’s top lawyer at the time, and Lisa Brummel (right), the company’s most senior human resources official, told Gates the emails were inappropriate and that he needed to stop, according to The Wall Street Journal

Gates reportedly agreed to stop corresponding with the woman. 

According to the Journal, Smith and Brummel informed the company board of the emails. The board met and determined that no further action was necessary since there wasn’t any physical altercation, according to the report. 

A spokesperson for Microsoft told the Journal that the company was made aware of Gates’ emails to the mid-level female employee in 2007 – just months before Gates was set to retire as a full-time employee.

The spokesperson, Frank Shaw, told the Journal that Gates offered to meet the woman outside of work and off campus.

‘While flirtatious, they were not overtly sexual, but were deemed to be inappropriate,’ he said. 

Shaw said that the employee never filed a complaint against Gates about the incident.  

Bridgitt Arnold, a spokesperson for Bill Gates, told the Journal: ‘These claims are false, recycled rumors from sources who have no direct knowledge, and in some cases have significant conflicts of interest.’ 

Brad Smith (left) currently serves as Microsoft’s president and chief legal officer. He is seen alongside CEO Satya Nadella, who continues to rely on Gates as a technical adviser

Maria Klawe, who was a director at Microsoft from 2009 to 2015, told The Wall Street Journal that while she was not aware of any specific complaints against Gates, she felt that he behaved as though the rules did not apply to him

Bill Gates’ affair in 2002 with a female subordinate came to light after the employee wrote to the board in 2019 detailing it – and allegedly asked that Gates’ estranged wife Melinda read the letter. The chairman of the board at the time, John W. Thompson (above), asked other members of the committee reviewing the letter not to reveal the existence of an investigation due to the sensitivity of the matter

Around the time that Gates’ wife petitioned for divorce earlier this year, news stories began to emerge about the Microsoft co-founder’s penchant for pursuing romantic relationships with female underlings. 

There were also several reports about Melinda’s unhappiness over Bill’s friendship with convicted pedophile Jeffrey Epstein. 

Earlier this year, it was learned that Gates had an ‘inappropriate’ sexual relationship with a different female staff member in 2002, and resigned while an investigation into the relationship was being investigated by the company board. 

The affair came to light after the Microsoft employee wrote to the board in 2019 detailing it – and allegedly asked that Gates’ estranged wife Melinda read the letter. 

The letter was seen by Smith, who is currently Microsoft’s president and vice chair, and CEO Satya Nadella. 

The chairman of the board at the time, John W. Thompson, asked other members of the committee reviewing the letter not to reveal the existence of an investigation due to the sensitivity of the matter, according to the Journal.

The board members who read the letter were then required to return their copies of the letter to the company’s general counsel.

It is considered unusual for a company conducting such an investigation not to notify all board members of its existence, according to legal experts who spoke to the Journal. 

‘While governance best practices are always evolving, the Board Chair and the Committee, with advice from outside legal counsel, decided to use the responsibility given to it and move forward with the initial stages of the review, recognizing that the matter could then move to the full Board in its later stages,’ Shaw told the Journal. 

Gates, 65, quit the board suddenly in March 2020 while the investigation was still underway. 

His spokeswoman confirmed there had been an affair almost 20 years ago but said his decision to leave Microsoft’s board was not linked to it. 

Gates’ ex-wife, Melinda Gates, was seen on Sunday departing Westchester County Airport north of New York City

Melinda Gates flew to Westchester County to attend the wedding of her 25-year-old daughter, Jennifer

The Journal reported on Monday that board members decided Gates should step down before the investigation was completed.

Current and former members of Microsoft’s board told the Journal they believe all matters related to Gates’ behavior toward female subordinates were handled appropriately by the company.

Maria Klawe, who was a director at Microsoft from 2009 to 2015, told the Journal that while she was not aware of any specific complaints against Gates, she felt that he behaved as though the rules did not apply to him.

‘He certainly gave the impression that he felt that he had a standing that gave him a particular, a set of rights, that other people wouldn’t have,’ Klawe, who is currently president of Harvey Mudd College, told the Journal.

In her 1998 book The Microsoft File, author Wendy Goldman Rohm claimed Gates was very far from the asexual geek many people assumed he was.

Rohm identified an attractive young sales manager at Microsoft’s German office with whom Gates had a globetrotting romance – five years after he started seeing Melinda.

 According to the Journal, at least one Microsoft board member was told by a top executive about an affair that then-CEO Gates had with a female Microsoft executive in 1992. The board was not notified of this, according to the Journal.

In the 1992 biography Hard Drive: Bill Gates and the Making of the Microsoft Empire, author James Wallace revealed Gates had an alleged affair with a married woman 13 years older than him when he was 27 years old.

Gates’ alleged affair was with the wife of an Osborne Computer executive who lived abroad, according to the biography. 

In 2006, Bill Gates allegedly asked a female Microsoft employee out to dinner in an email after attending a presentation she had given, The New York Times reported. 

‘If this makes you uncomfortable, pretend it never happened,’ Gates wrote in the email obtained by The New York Times

The woman took his advice and pretended it never happened.

A couple of years later, Gates asked out an employee with the Bill and Melinda Gates Foundation.

The pair were in New York for a work trip, when he told her: ‘I want to see you. Will you have dinner with me?’

The woman told the Times the approach made her feel uncomfortable, but she laughed it off.

The report said there was no expectation that the women would suffer professional repercussions for spurning Gates’ advances. 

A photo shows Bill and Melinda Gates while they were dating before getting married in 1994

The ex-couple are pictured with their three kids Jennifer (center), Rory (right) and Phoebe (left) in 2019

It’s not clear whether Melinda was aware of her husband’s advances.    

The Microsoft co-founder and his wife announced in May they were ending their 27-year marriage.

A King County, Washington State Superior Court judge signed the dissolution decree in August. The New York Times reports the court documents didn’t detail how they would divide their assets.

Bill Gates was formerly the world’s richest person and his fortune is estimated at about $132.7billion.

They met after she began working at Microsoft as a product manager in 1987. The two were married in 1994 in Hawaii.

The Seattle-based Bill and Melinda Gates Foundation is the most influential private foundation in the world, with an endowment worth about $50billion.

It has focused on global health and development and US education issues since incorporating in 2000. 

The two have said they will continue to work together as co-chairs of their foundation.

However, if after two years Bill and Melinda decide they cannot continue in their roles, Melinda will resign her positions as co-chair and trustee, The Bill and Melinda Gates Foundation announced in August.

If Melinda resigns, Gates would essentially buy her out of the foundation, one of the world’s largest private charitable organizations, and she would receive resources from him to do her own philanthropic work.

The resources received would be separate from the foundation’s endowment, according to foundation.

Despite the acrimonious end to their marriage, the former couple reunited over the weekend in Westchester County, New York for the wedding of their oldest daughter, 25-year-old Jennifer Gates (seen second from right in between her parents on Saturday) 

Jennifer Gates poses for photos with her new husband Nayel Nassar as she celebrates her wedding at her 142-acre, $16 million North Salem farm in a reported $2million ceremony

In July, it was reported that Bill was on the verge of tears when he told an audience of wealthy business magnates in Idaho that it was his fault the marriage to Melinda ended.

During an ‘off the record’ question-and-answer session at the Allen & Co. conference in Sun Valley, Idaho in July, the New York Post reported that Gates ‘fessed up to messing up.’

‘He basically referred to the fact that it [the divorce] was his fault,’ a source told the newspaper.

The source added: ‘He did seem a bit emotional about it. He might have been on the verge of tears.’  

Melinda, who now goes by Melinda French Gates, was also upset at the way allegations of sexual harassment against Michael Larson, one of Gates’ key lieutenants and the manager of his personal fortune, were handled. 

Four Microsoft employees accuse Bill Gates of being an office ‘bully’ whose catchphrase was ‘that’s the stupidest f*****g idea I’ve ever heard’ and claim he pursued sexual affairs with employees and journalists 

In June, four Microsoft employees accused company co-founder Bill Gates of being an office ‘bully’ whose catchphrase was ‘that’s the stupidest f*****g idea I’ve ever heard’ and claimed he pursued sexual affairs with employees and journalists.

Gates’ reputation as a hot-tempered boss began not long after he launched tech giant Microsoft with childhood friend Paul Allen in 1975, Insider reported. 

A spokesperson for the billionaire has denied he mistreated employees.

Gates, 65, came under scrutiny after he and Melinda Gates announced their divorce in May and reports emerged of his alleged extramarital affairs and concerns over the nature of his relationship with convicted pedophile Jeffrey Epstein

A former Microsoft executive who spoke on condition of anonymity told Insider that ‘having a meeting with Bill was just an opportunity to get yelled at, so I tried to avoid that.’

Four Microsoft employees have accused founder Bill Gates of being an office ‘bully’ whose catchphrase was ‘that’s the stupidest f*****g idea I’ve ever heard’ and claimed he pursued sexual affairs with employees and journalists. Gates is pictured in New York City in May

Bill Gates, left, is pictured with Jerrold Kaplan and Mitchell Kapor at an annual conference in Naples, Florida in  1988. Gates was allegedly often inebriated at tech events and after-parties and ‘got drunk pretty easily’

Other sources who spoke to Insider described his catchphrase as ‘That’s the stupidest f**king idea I’ve ever heard’ and said he was known for swearing at his employees.

Gates would allegedly track his employees by memorizing their license plates, according to the outlet.

Some Microsoft workers who spoke to the outlet, however, defended Gates with one saying he ‘yelled at everyone the same’ and that she appreciates his candor but conceded that his management style could intimidate some employees.  

‘He doesn’t know how to joke really or how to connect with people,’ said another former executive, who described solo meetings with Gates as awkward.

‘If he told you he liked your hair, he wasn’t trying to flirt with you. He just actually liked your hair.’

A current Microsoft employee told Insider: ‘He’s just an awkward human being as far as social interactions go.’

Maria Klawe, a former Microsoft board member from 2009 to 2015, said ‘a person like Bill Gates thinks the usual rules of behavior don’t apply to him’ and accused him of being unreceptive to suggestions about improving diversity.

Klawe said that Gates behaved as if he was the ‘smartest person in the room’ and that diversity was not something Gates ‘was interested in hearing about.’ 

Maria Klawe, a former Microsoft board member from 2009 to 2015, right, said that ‘a person like Bill Gates thinks the usual rules of behavior don’t apply to him’ 

Klawe said that Gates behaved as if he was the ‘smartest person in the room’ and that diversity was not something Gates ‘was interested in hearing about’ 

She said that when female executives would suggest diversity initiatives, Gates would allegedly respond with: ‘Are you trying to effing destroy the company?’ 

The spokesperson for Gates told Insider that Klawe’s allegations are a ‘gross mischaracterization.’

Gates’ relationships and encounters with employees have long been a topic of discussion surrounding the billionaire, according to the outlet.

Melinda Gates herself was an employee at Microsoft, having been hired as a product manager in 1987, when the billionaire first asked her out months after flirting with her at a conference dinner. 

In 2006, Bill Gates allegedly asked a female Microsoft employee out to dinner in an email after attending a presentation she had given, The New York Times reported. 

Melinda Gates herself, pictured, was an employee at Microsoft, having been hired as a product manager in 1987, when the billionaire first asked her out months after flirting with her 

‘If this makes you uncomfortable, pretend it never happened,’ Gates wrote in the email obtained by The New York Times.

A Gates Foundation employee told the outlet that the billionaire asked her on a date while they were at a cocktail party in New York. 

‘I want to see you. Will you have dinner with me?’ Gates allegedly told the woman. 

In the 1992 biography Hard Drive: Bill Gates and the Making of the Microsoft Empire, author James Wallace revealed Gates had an alleged affair with a married woman 13 years older than him when he was 27 years old.

Gates’ alleged affair was with the wife of an Osborne Computer executive who lived abroad, according to the biography.

An Osborne Computer executive who knew about the alleged affair told Wallace that ‘Bill had a real fondness for older women then.’

Adam Osborne, who developed the first commercially successful PC known as Osborne 1, allegedly demanded that Gates stop seeing the wife of his employee.

‘Gates told Osborne to mind his own business,’ Wallace wrote.

Gates himself told BBC that he would hack his school’s scheduling software to ensure he would be the only boy in class.

Gates had an alleged affair with a married woman 13 years older than him when he was 27 years old

‘I was the one who benefited by being able to have the nice girls at least sit near me. It wasn’t that I could talk to them or anything, but they were there,’ Gates said.

Wallace told Insider that, while Gates attended Harvard University in 1973, he would allegedly visit strip clubs in an area of Boston once referred to as the Combat Zone because of its notorious strip clubs, porn theaters, and prostitution.

Gates himself admitted to frequenting the area, centered on Washington Street between Boylston Street and Kneeland Street, in a 1994 interview he did with Playboy magazine.

‘Just because I went there doesn’t mean I engaged in everything that was going on,’ Gates said.

‘I ate pizza, read books and watched what was going on. I went to the diners.’

Wallace claimed to Insider that Gates’ penchant for socializing with women remained even after he started dating Melinda Gates in 1987.

Gates was allegedly known to invite friends to swim naked at his bachelor pad in Laurelhurst where he ’rounded up’ dancers from local all-nude nightclubs, Wallace said.

‘I don’t know if he physically transported them or if he just told them where to show up,’ Wallace told the outlet.

Robert X. Cringely, who wrote a popular computer gossip column for InfoWorld, told Insider that Gates was allegedly often inebriated at tech events and after-parties and that he ‘got drunk pretty easily.’

Bill Gates is pictured in a 1977 police mugshot when he was arrested for bad careless driving in Albuqerque, New Mexico

‘All of us will have been at some affair where Bill was clearly impaired. He was happier’ drunk, Cringely said.

Gates, then 33, took a helicopter to Les Arcs ski resort in the French Alps for an international sales meeting for Microsoft in the summer of 1988 where he was allegedly caught lying on top of a woman on the lawn.

The pair were ‘just snuggling’ after Gates joined his employees for drinks in a Swiss chalet and partied until the early morning, Dan Graves, a former Microsoft export manager, told Insider.

After he started dating Melinda, Gates allegedly struggled to commit to her and she was allegedly aware of his ‘womanizing,’ the outlet reported. The couple even broke up for at least a year early in their relationship. 

‘Bill wanted to be married, but he didn’t know whether he could actually commit to it and have Microsoft,’ Melinda said in an interview for the Netflix docuseries Inside Bill’s Brain: Decoding Bill Gates.

Even after marrying Melinda, Gates told Time magazine in 1997 that he still went on annual vacations to the Outer Banks of North Carolina with his ex-girlfriend Ann Winblad, the software entrepreneur whom he had dated from 1984 to 1987.

Bill and Melinda Gates’  personal affairs have been managed by Watermark Estate Management since at least 2001, which would allegedly arrange Gates’ annual beach trips with Winblad. 

Meanwhile, Gates is reported to have taken meetings with Epstein including a flight to Palm Beach on Epstein’s private plane.

Bill Gates, not pictured, still went on annual vacations to the Outer Banks of North Carolina with his ex-girlfriend Ann Winblad, pictured, the software entrepreneur whom he had dated from 1984 to 1987, even after marrying Melinda Gates

Gates’ spokesperson told the outlet that Gates had ‘absolutely no business partnership or personal friendship’ with Epstein, and any meetings between the two were about philanthropy.

‘It is extremely disappointing that there have been so many lies published about the cause, the circumstances and the timeline of Bill Gates’s divorce,’ the spokesperson said. 

‘The rumors and speculation surrounding Mr. Gates are becoming increasingly absurd and it’s unfortunate that people who have little to no knowledge are being characterized as ‘sources.”

Gates’ relationship with Epstein reportedly dates back to 2011, but it became a point of contention for the couple in September 2013, the Daily Beast reported. 

Melinda Gates reportedly told friends she was furious about their alleged friendship and wanted nothing to do with Epstein but sources said Bill Gates allegedly visited Epstein’s house numerous times.

Bill Gates even reportedly talked about his ‘toxic’ marriage to Epstein who allegedly gave Gates advice on ending his marriage, according to the Daily Beast.

Wallace claimed to Insider that ‘there were some big-name journalists who knew about this behavior’ over the years.

Bill Gates, and Microsoft co-founder Paul Allen, are pictured in 1987. Allen said in his memoir that Gates tried to dilute his equity in the company because he was ‘unproductive’ while dealing with his first bout of cancer

However, they ‘never reported on it because they knew Microsoft would have taken away their access,’ he said.

Gates allegedly even gained a reputation for hitting on female reporters who covered industry conferences such as Comdex, Wallace said. 

‘The journalists said that it was their understanding that they weren’t the only ones either,’ he added.

Stories about Gates have allegedly been kept quiet over the years but ‘the halo broke’ when  Melinda divorced Gates, a Microsoft employee told Insider. 

‘Anyone who had stories could bring all those stories out,’ the source said.        

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