The end of the affair? Not for Eric Schmidt.

Schmidt and Simon were seen together on the French Riviera, at tech conferences and on New York’s Fire Island, where she owned a beach house. When a large yellow diamond ring was spotted on Simon’s finger, some speculated in the media that Schmidt might divorce his wife and marry Simon.

But Schmidt moved on to other girlfriends. Although he and Simon, who divorced her husband, later rekindled their relationship in the late 2000s and early 2010s, they decided to go their separate ways in 2014, people with knowledge of their relationship said.

For billionaires, and the people who love them, breaking up can be a little like unraveling a corporate merger gone wrong. Ending Schmidt’s affair has taken a decade — so far. There have been contracts, amended contracts, arbitrations, lawsuits and the platoon of advisers that inevitably go along with all that.

Schmidt, now 69, approved a confidential settlement in 2014 with Simon that paid her an undisclosed amount of money and appointed an adviser, Derek Rundell, to set it up. Under the arrangement, Simon would bring Schmidt investment ideas that Rundell would evaluate on his behalf.

But the deal imploded when Simon and Rundell fought bitterly, leading to years of wrangling that culminated in accusations of fraud against Simon last year over an investment in luggage maker Away. Simon has denied committing fraud.

During his years leading Google, Schmidt was famously known as the adult supervision, a brainy, button-down sage who mentored the internet firm’s young founders, Larry Page and Sergey Brin, and propelled the company to great heights. Since leaving the board of Google’s parent company in 2019, he has cultivated that image further, parlaying his net worth of about $35 billion into an influential role advising the U.S. government on defense and artificial intelligence policy and making his mark with splashy initiatives in the world of philanthropy.

Yet, over the past decade, his management of personal matters has been fraught, at times lacking the kind of discipline he brought to running Google. In March, Simon filed an arbitration case against Schmidt in California, seeking to free herself from the confidentiality clauses of their 2014 settlement. More of his secrets threaten to spill out.

The New York Times pieced together Schmidt’s tangled history with Simon and Rundell from records of six separate litigation and arbitration cases, all of which are public. Schmidt’s name is redacted or withheld in four of the cases, but the Times confirmed his identity through people with knowledge of some of the events and by triangulating information from court filings.

The settlement

Simon, 61, who left public relations firm Burson-Marsteller and founded her own PR company in 2019, was one of a series of women with whom Schmidt had extramarital affairs over the past 20 years. Throughout, he has remained married to Wendy Schmidt, his wife of 44 years, although they lead largely separate lives.

In a 2012 interview with the Times, Wendy Schmidt shrugged off media reports of her husband’s relationships. “You know, people will write things,” she said. “You just have to ignore them.”

Eric Schmidt and Simon started appearing publicly together in the mid-2000s. Neither made much of an attempt to keep the relationship secret; Simon openly talked about it with some journalists.

After a hiatus of a few years during which Eric Schmidt dated a former CNBC reporter, Kate Bohner, he and Simon got back together in 2009 and saw each other on and off for several more years. In the summer of 2014, they parted ways.

Eric Schmidt had paid certain expenses for Simon for years, which were memorialized in several legal agreements. He proposed a new financial arrangement to provide for Simon and her family, people with knowledge of the conversations said.

Schmidt put Rundell in charge of crafting the deal.

Rundell had entered Schmidt’s orbit through Gary Coursey, a financial adviser known by the nickname Court who helped Schmidt make venture capital investments. Rundell and Coursey had met at the University of Colorado Boulder in the early 1990s, later sold an email company to WebMD and briefly advised pop star Michael Jackson in the early 2000s.

After Coursey introduced them, Rundell became something of a fixer for Schmidt. Rundell was “a person who could solve special and hard problems,” Schmidt testified in one arbitration proceeding.

The Information earlier reported on Rundell’s work for Schmidt.

Rundell, 53, did not reply to requests for comment.

At Schmidt’s request, Rundell put together the confidential settlement with Simon, which firmly nudged the relationship from romantic to transactional. Under the terms of the agreement, dated Sept. 19, 2014, Simon agreed to become a paid consultant to a Nevada limited liability company called Maple Beach Ventures.

Maple Beach Ventures was essentially a small venture capital fund managed by Rundell and funded by Schmidt. Simon would receive payments for bringing startup investment ideas to Rundell. If Rundell liked them, Schmidt would invest in the startups through Maple Beach Ventures. The agreement included confidentiality, so Simon could not disclose Schmidt’s involvement in the investments.

It’s unclear how much Schmidt paid Simon. A copy of the settlement filed in court as part of an arbitration shows that she was entitled to a one-time fee and to annual and monthly payments, but the numbers are redacted. Simon was also entitled to 20% of the profit Schmidt made from any investment she brought.

Around the time he structured the settlement with Simon, Rundell also acted as the go-between for the purchase of a horse farm in New York’s Hudson Valley for another of Schmidt’s girlfriends, Lisa Shields. For these and other services, Schmidt paid Rundell a fee of $47,500 a month until June 30, 2016, according to a copy of their agreement.

Tempers flare

The settlement with Simon didn’t bring peace for long.

Within months, Simon and Rundell began butting heads. Simon complained that Rundell didn’t act on most of the investment ideas she brought, while Rundell faulted Simon for not conducting proper due diligence on the investments she proposed.

In March 2015, Simon complained to Schmidt that Rundell had responded to only nine of the 43 investment opportunities she had presented to him and that Maple Beach Ventures had invested in only six of them. Schmidt responded that most “VCs see 100 or more deals for every one deal they invest in.”

He suggested a compromise: Simon could have a sum she invested at her own discretion each quarter, provided she followed a strict due diligence process. (The figure was redacted.)

Following up on Schmidt’s suggestion, Rundell sent Simon a proposal with an updated investment budget and new due diligence procedures. But Simon turned it down because she found the procedures too onerous and resented that the investments would still have to go through Rundell, according to arbitration filings.

As Simon and Rundell haggled, she flew to Europe to attend a networking event for entrepreneurs in the French Alps. There she met Jen Rubio, who had just co-founded a luggage startup called Away. Between runs on the slopes of the famed Méribel ski resort, Rubio mentioned that Away was raising money from family and friends in what is known as a “seed round” and invited Simon to participate.

A few weeks later, Simon emailed Rubio to say she would invest $25,000 through Maple Beach Ventures. Simon could not disclose Schmidt’s involvement under their 2014 agreement.

“I am really excited to be a part of Away and also to help watch you grow and build the company and I am here for you,” Simon emailed Rubio in April 2015.

Simon arranged a call between Rubio and Rundell to finalize the investment but didn’t explain who Rundell was, a person with knowledge of the matter said. Rubio assumed — incorrectly — that Maple Beach Ventures was Simon’s company and that Rundell was an employee who worked for her, this person said.

Simon and Rundell’s relationship continued deteriorating. Around the same time, Simon had asked Schmidt for a loan to buy a house. Schmidt agreed to lend her the money against the proceeds of an investment he had made in Uber several years earlier. The investment had come from an introduction Simon had made.

Under a deal that predated their 2014 settlement, Schmidt had agreed to pay her 10% of whatever profit he earned from Uber. But the ride-hailing company was still private, so calculating the value of Simon’s stake to determine the loan size was difficult. Months of negotiations between Rundell and a lawyer representing Simon ensued. At one point, Simon objected to a $125,000 fee Rundell wanted to deduct from the loan amount.

In March 2016, the loan negotiations broke down, and Simon sent Schmidt an angry email threatening to go public about their confidential deal.

Rundell’s behavior was “not acceptable” and she had “an awesome case here,” she wrote. “This is going mainstream and I am lawyering UP.”

A few hours later, she followed up: “Let me know if you want to take this public.”

Later that year, the two sides resolved their differences. Under an amendment to the 2014 settlement, Schmidt agreed to make monthly payments of $5,000 and quarterly “catch-up” payments of $15,000 to Simon, on top of other payments laid out in the original agreement. He also agreed to cover unspecified tuition payments and to reimburse Simon for the $21,000 she had spent on legal fees.

But within months, Simon and Rundell resumed bickering.

Simon again complained that Rundell was ignoring most of the investment ideas she brought to him. Rundell responded that Simon wasn’t giving him the documentation she was required to provide for each investment.

Lawyers were summoned again, but this time no compromise was found.

In June 2018, a lawyer for Maple Beach Ventures informed Simon that her consulting agreement was being terminated. She responded in April 2019 by starting a confidential arbitration proceeding against the company for breach of contract.

A tender offer

While Simon’s dispute with Rundell and Schmidt escalated, Rubio’s startup was thriving. Thanks partly to savvy online marketing, Away’s stylish luggage was becoming ubiquitous at U.S. airports. By early 2019, the New York-based company had sold more than 1 million suitcases.

That May, just weeks after Simon took Schmidt and Rundell to arbitration, a group of institutional investors led by Wellington Management offered to buy the shares of Away’s early investors at a premium to their original price, in what is known as a tender offer. Away was now valued at a stunning $1.4 billion, up from $7.2 million four years earlier. The 266,638 shares that Maple Beach Ventures had purchased for $25,000 in 2015 were worth $2.83 million.

Away transmitted the tender offer to Simon. Rubio remained under the impression that Maple Beach Ventures was Simon’s company and that the $25,000 seed investment had been made with her money, a person familiar with the matter said.

What happened next is under dispute. In a lawsuit that Away filed late last year against Simon, the company claimed that she took and profited from shares that weren’t hers. Simon has countered that the shares were, in fact, hers.

Underlying the disagreement was Simon’s 2014 deal with Schmidt. Under its terms, she was entitled to 20% of the profit that Maple Beach Ventures reaped from any investment she originated, which would have come to about $561,000 before taxes for Away — but only if she were still employed as a consultant to the company when the investment was sold. Her 2018 termination meant she would get nothing.

That did not sit well with Simon, so she came up with a subterfuge, according to Away’s lawsuit. Rather than forwarding the tender offer transmittal letter to Rundell, Simon created a new Maple Beach Ventures LLC on May 10, 2019. Unlike the original Maple Beach Ventures, which Rundell had registered in Nevada, Simon incorporated this one in Delaware and designated herself as its sole principal, Away claimed.

Three weeks later, Simon signed the tender offer paperwork, presenting the new Maple Beach Ventures as the owner of the shares, according to Away’s lawsuit.

Away said it didn’t spot the alleged sleight of hand when it received Simon’s paperwork. It canceled the original Maple Beach Ventures’ shares in its company records, reissued them to the investor group conducting the tender offer and wired $2.83 million to a Citibank account that Simon had created in the name of the new, Delaware-registered Maple Beach Ventures.

Rundell and Schmidt, who were never notified about Away’s tender offer, had no idea what transpired, people with knowledge of the matter said.

Simon has countered in court filings that it was always understood that the Away shares were hers, even though they were held under Maple Beach Ventures’ name. In the court filings, she has said she was being prevented from giving the full story by the confidentiality clauses in the 2014 settlement with Schmidt.

In late 2019, a few months after Simon sold the Away shares, Schmidt’s relationship with Rundell began falling apart. Coursey, who had introduced Rundell to Schmidt, was now feuding with Rundell, who owed him money. Rundell asked Schmidt to cover his debt, people familiar with the men said.

When Schmidt refused, Rundell claimed ownership of the Hudson Valley horse farm Schmidt had bought for Shields, according to people familiar with the matter and arbitration filings. (Rundell had leverage because the farm had been purchased under his name, the people said.) In May 2020, Schmidt took Rundell to arbitration over the farm.

To get Schmidt to back off, Rundell filed a counterclaim in which he said Simon and Shields had threatened to air salacious allegations about Schmidt’s private life. Among the allegations: that Schmidt used illicit drugs; that he passed on sexually transmitted diseases to multiple partners; that he participated in orgies and in a sex tape; and that he had sex with prostitutes, according to an arbitration filing made public in court.

Shields denied making the allegations or having any knowledge of them during the arbitration.

Referring to the allegations, Matthew Hiltzik, a spokesperson for Schmidt, said, “Mr. Schmidt refuses to be intimidated by those who threaten to coerce or extort him.”

While Schmidt and Rundell battled, Simon won her breach of contract arbitration against the original Maple Beach Ventures in January 2021. The arbitrator ordered the company to pay her $461,113, plus interest on a portion of it, and reaffirmed her 10% stake in any Uber profit.

The rancor between Schmidt and Rundell continued escalating. After prevailing in the dispute over the farm, Schmidt initiated a second arbitration against Rundell in late 2021 over Maple Beach Ventures and several other companies Schmidt had funded.

Hiltzik said Schmidt responded to Rundell’s “tactics by prosecuting and prevailing in two separate arbitrations and recovered millions of dollars.”

During the second proceeding, Schmidt learned what happened to the Away investment. When one of his employees tried to find out the investment’s status, Away said Maple Beach Ventures was no longer an investor because Simon had tendered its shares in the 2019 offer.

Schmidt was furious. His lawyers threatened to sue Away if his shares weren’t reinstated.

In its lawsuit, Away said it was then that it realized that Maple Beach Ventures wasn’t Simon’s company. In early 2023, Away settled the matter with Schmidt by paying him $3.5 million, which included interest.

In November, Away sued Simon for carrying out what it described as a “fraudulent and deceptive scheme.”

In a statement, an Away spokesperson said it “has been unfairly drawn into this matter, which does not directly concern us. This has led our company to incur significant expenses, which we are now seeking to recover.”

The case is pending in New York State Supreme Court. Simon has separately begun an arbitration proceeding against Schmidt to unshackle herself from the confidentiality clauses of their 2014 deal to better defend herself.