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Jamie Dimon turned down Jeff Bezos and a top gig at Amazon to take on ‘troubled’ Bank One in a $60 million bet

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In 1998, Jamie Dimon was a rising star on Wall Street, widely expected to assume the CEO mantle at Citigroup after helping build the financial conglomerate alongside his mentor Sandy Weill. That path abruptly collapsed when Dimon was unceremoniously fired, as Dimon recalled in a recent podcast appearance.

Speaking to Acquired, the JPMorgan Chase CEO said the shock was not just professional but deeply personal; Dimon recalls fielding nervous questions from his children about the family’s future as about 50 colleagues gathered at his apartment for “a wake” that night. Dimon said he told his guests that he was doing alright, it was his “net worth, not his self worth” that had been shaken.

Dimon said he spent the next 18 months considering his next step, out of an office in the Seagram Building. He said he dabbled in teaching, considered starting his own merchant bank, and even contemplated retirement, being 42 years old at the time. But he also called various connections, keeping an open-mind. One of these led to a visit to Seattle to meet Amazon founder Jeff Bezos, who was seeking a president for his fast-growing company, and they had a particularly consequential conversation.

The Amazon what-if and the road not taken

Dimon and Bezos hit it off, saying they’ve “been friends ever since.” Yet he also says it was just “a bridge too far,” not just to move to Seattle, but to leave finance for the tech world, and running Amazon full-time. Dimon said he would have been stepping into a radically different industry and life, joking that it would have been like a “When Harry Met Sally” scenario or an alternate universe: “I’ll never wear a suit again. I’m going to live in a houseboat.”

To be sure, Amazon at that time was also a much different proposition to the $2.4 trillion colossus it is today. The tech company’s share price was less than a dollar and it had just a $5.5 billion market cap at the end of 2000. After the Amazon visit, Dimon said he “got serious” and considered other positions.

Other offers included running other global investment banks, which Dimon declined to name, and even insurance giant AIG, as he fielded a call from Hank Greenberg. Another offer he declined was from Ken Langone, Bernie Marcus and Arthur Blank, and Dimon said he had good conversations, but eventually confessed that he had never actually stepped foot in a Home Depot before.

But what stuck was a headhunter’s call about Bank One—a large but beleaguered Chicago bank. At the time, Bank One was valued around $20 billion, a far cry from the $200 billion scale of Citigroup. It had recently merged with other regional banks and was beset by infighting, brand confusion, and mounting losses. Dimon recalled that analyst Mike Mayo had a great line at the time about the bank’s problems: “Even Hercules couldn’t fix it.”

How Dimon became the captain of the ship

Undeterred by the daunting turnaround task, Dimon saw potential where others saw wreckage. He described the idea of another banking job as “my habitat”—and he described Bank One as a place where his operational style and relentless focus on risk management could make an impact. He uprooted his young family, moved to Chicago, and signaled ultimate commitment by investing half his net worth—$60 million—directly into Bank One’s stock the day he took the job. “I was going to go down with the ship or up with the ship,” he said, determined to demonstrate to shareholders and his new team that he was “alock, stock, and barrel.”

He also talked generally about why he made this particular career decision instead of a New York-based investment banking job. He was in charge at Bank One as the CEO, he said, whereas he expressed doubts about whether he could fully trust people in the investment banking world, after his bruising experience with his mentor Sandy Weill and Citigroup.

Within days, he confronted the scale of the challenge: management discord, disjointed IT systems, failing credit card operations, and a 21-member board split by tribal rivalries. Rather than seek short-term wins, Dimon insisted on honest reporting, transparent communication, and building a long-term strategy—traits that would later crystallize at JPMorgan Chase and Dimon’s belief in having a “fortress balance sheet.” He explained on the podcast that Bank One’s tolerance for risk was far too excessive and the bank wasn’t being honest with itself. By owning up to its own problems, it could set course for a stronger balance sheet that would be a fortress when the market turned.

Captain of the ship or the houseboat?

Dimon’s wager on Bank One—and the leadership approach he honed there—set the stage for his stewardship of JPMorgan Chase. He made his return to Wall Street in 2004 when Bank One merged with JPMorgan, and he emerged as one of the great stabilizers of the financial system during the 2008 financial crisis. As JPMorgan has gone from strength to strength, Dimon has matured into a senior voice in American society itself, weighing in on politics and central banking alike, and wielding substantial influence.

American finance might look profoundly different if Dimon had taken Bezos’ offer and chosen to join Amazon. Instead, his $60 million bet on a struggling bank catalyzed one of the most remarkable second acts in corporate American history, ultimately leading to one of the most successful and influential bankers of his generation. Instead, he could have been a tech executive living on the proverbial houseboat.

JPMorgan declined to comment further for this report.

For this story, Fortune used generative AI to help with an initial draft. An editor verified the accuracy of the information before publishing. 



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The $124 trillion Great Wealth Transfer is intensifying as inheritance jumps to a new record

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Nearly $300 billion was inherited this year as the Great Wealth Transfer picks up speed, showering family members with immense windfalls.

According to the latest UBS Billionaire Ambitions Report, 91 heirs inherited a record-high $297.8 billion in 2025, up 36% from a year ago despite fewer inheritors.

“These heirs are proof of a multi-year wealth transfer that’s intensifying,” Benjamin Cavalli, head of Strategic Clients & Global Connectivity at UBS Global Wealth Management, said in the report.

Western Europe led the way with 48 individuals inheriting $149.5 billion. That includes 15 members of two “German pharmaceutical families,” with the youngest just 19 years old and the oldest at 94.

Meanwhile, 18 heirs in North America got $86.5 billion, and 11 in South East Asia received $24.7 billion, UBS said.

This year’s wealth transfer lifted the number of multi-generational billionaires to 860, who have total assets of $4.7 trillion, up from 805 with $4.2 trillion in 2024.

Wealth management firm Cerulli Associates estimated last year that $124 trillion worldwide will be handed over through 2048, dubbing it the Great Wealth Transfer. More than half of that amount will come from high-net-worth and ultra-high-net-worth people.

Among billionaires, UBS expects they will likely transfer about $6.9 trillion by 2040, with at least $5.9 trillion of that being passed to children, either directly or indirectly.

While the Great Wealth Transfer appears to be accelerating, it may not turn into a sudden flood. Tim Gerend, CEO of financial planning giant Northwestern Mutual, told Fortune’s Amanda Gerut recently that it will unfold more gradually and with greater complexity

“I think the wealth transfer isn’t going to be just a big bang,” he said. “It’s not like, we just passed peak age 65 and now all the money is going to move.”

Of course, millennials and Gen Zers with rich relatives aren’t the only ones who sat to reap billions. More entrepreneurs also joined the ranks of the super rich.

In 2025, 196 self-made billionaires were newly minted with total wealth of $386.5 billion. That trails only the record year of 2021 and is up from last year, which saw 161 self-made individuals with assets of $305.6 billion.

But despite the hype over the AI boom and startups with astronomical valuations, some of the new U.S. billionaires come from a range of industries.

UBS highlighted Ben Lamm, cofounder of genetics and bioscience company Colossal; Michael Dorrell, cofounder and CEO of infrastructure investment firm Stonepeak; as well as Bob Pender and Mike Sabel, cofounders of LNG exporter Venture Global.

“A fresh generation of billionaires is steadily emerging,” UBS said. “In a highly uncertain time for geopolitics and economics, entrepreneurs are innovating at scale across a range of sectors and markets.”



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Apple rocked by executive departures, with chip chief at risk of leaving next

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Apple Inc., long the model of stability in Silicon Valley, is suddenly undergoing its biggest personnel shake-up in decades, with senior executives and key engineers both hitting the exits.

In just the past week, Apple’s heads of artificial intelligence and interface design stepped down. Then the company announced that its general counsel and head of governmental affairs were leaving as well. All four executives have reported directly to Chief Executive Officer Tim Cook, marking an exceptional level of turnover in Apple’s C-suite. 

And more changes are likely coming. Johny Srouji — senior vice president of hardware technologies and one of Apple’s most respected executives — recently told Cook that he is seriously considering leaving in the near future, according to people with knowledge of the matter. Srouji, the architect of Apple’s prized in-house chips effort, has informed colleagues that he intends to join another company if he ultimately departs.

At the same time, AI talent has been fleeing for tech rivals — with Meta Platforms Inc., OpenAI and a variety of startups poaching many of Apple’s engineers. That threatens to hamper the company’s efforts to catch up in artificial intelligence, an area where it’s struggled to make a mark. 

It all adds up to one of the most tumultuous stretches of Cook’s tenure. Though the CEO himself is unlikely to leave imminently, the company has to rebuild its ranks and figure out how to thrive in the AI era. 

Within the company, some of the departures are cause for deep concern — with Cook looking to stave off more with stronger compensation packages for key talent. In other cases, the exits just reflect the fact that veteran executives are nearing retirement age. Still, many of the shifts constitute a disconcerting brain drain.

While Cook maintains that Apple is working on the most innovative product lineup in its history — a slate that’s expected to include foldable iPhones and iPads, smart glasses, and robots — Apple hasn’t launched a successful new product category in a decade. That leaves it vulnerable to poaching from a range of nimbler rivals better equipped to develop the next generation of devices around AI.

A spokesperson for Cupertino, California-based Apple declined to comment.

The exit of Apple’s AI chief, John Giannandrea, followed a number of stumbles in generative AI. The company’s Apple Intelligence platform has suffered from delays and subpar features. And a highly touted overhaul to the Siri voice assistant is roughly a year and a half behind schedule. Moreover, the software will rely heavily on a partnership with Alphabet Inc.’s Google to fill the gaps in its capabilities.

Against that backdrop, Apple began phasing Giannandrea out of his role in March but is allowing him to remain until next spring.

Within Apple, employees have long expected Giannandrea to step aside — and some have expressed surprise that he’s sticking around as long as he is.

But parting ways with Giannandrea sooner would have been taken as public acknowledgment of a problem, people familiar with the situation said. 

Design veteran Alan Dye, meanwhile, is heading to Meta’s Reality Labs unit — a remarkable defection to one of Apple’s fiercest rivals.

Within a day of that news, Apple turned around and announced that it had poached one of Meta’s executives. Jennifer Newstead, chief legal officer at the social networking company, will become Apple’s general counsel. She helped oversee Meta’s successful antitrust battle with the US Federal Trade Commission — experience that’s likely to prove useful in Apple’s own legal fight with the Justice Department over alleged anticompetitive practices.

Read More: Apple Taps Meta Lawyer as General Counsel in Latest Shake-Up

Newstead is taking over for Kate Adams, who served eight years in the role and will retire in late 2026. Lisa Jackson, vice president for environment, policy and social initiatives, is retiring as well — and her duties will be divided up among other executives. 

Though the news of Adams’ departure was jarring — especially considering the number of Apple legal disputes currently on her plate — she’s had a fairly long tenure for a general counsel at the company.

Jackson, meanwhile, was widely expected to be leaving soon. The former Obama administration official has kept a lower profile during President Donald Trump’s second term, opting to dispatch deputies to handle discussions with the White House. Bloomberg News had previously reportedthat she was considering retirement.

These exits follow an even bigger departure. Jeff Williams, Cook’s longtime No. 2, retired last month after a decade as chief operating officer. Another veteran leader, Chief Financial Officer Luca Maestri, stepped into a smaller role at the start of 2025 and is likely to retire in the not-too-distant future.

The flurry of retirements reflects a demographic reality for Apple. Many of its most senior executives have been at the company for decades and are roughly the same age — either in their 60s or nearing it.

Cook turned 65 last month, fueling speculation that he would join the exodus. People close to the executive have said that he’s unlikely to leave soon, though succession planning has been underway for years. John Ternus, Apple’s 50-year-old hardware engineering chief, is considered by employees to be the frontrunner CEO candidate.

When Cook does step down, he’s likely to shift into the chairman job and maintain a high level of influence over the iPhone maker. That makes it unlikely that Apple will select an outsider as the next CEO, even as executives like Nest Labs founder Tony Fadell are being pushed as candidates by people outside the company. Though Fadell helped invent Apple’s iconic iPod, he left the tech giant 15 years ago on less-than-friendly terms. 

For now, Cook remains active at Apple and travels extensively on behalf of the company. However, the executive does have an unexplained tremor that causes his hands to shake from time to time — something that’s been discussed among Apple employees in recent months.

The shaking has been noticed by both executives and rank-and-file staff during meetings and large company gatherings, according to people familiar with the matter. But people close to Cook say he is healthy and refute rumors to the contrary that have circulated in Silicon Valley.

Read More: The Apple Insiders in the Running to Succeed Cook

A more imminent risk is the departure of Srouji, the chip chief. Cook has been working aggressively to retain him — an effort that included offering a substantial pay package and the potential of more responsibility down the road. One scenario floated internally by some executives involves elevating him into the role of chief technology officer. Such a job — overseeing a wide swath of both hardware engineering and silicon technologies — would potentially make him Apple’s second-most-powerful executive.

But that change would likely require Ternus to be promoted to CEO, a step the company may not be ready to take. And some within Apple have said that Srouji would prefer not to work under a different CEO, even with an expanded title.

If Srouji does depart, which isn’t yet a certainty, the company would likely tap one of his two top lieutenants — Zongjian Chen or Sribalan Santhanam — to replace him.

The recent shifts are already reshaping Apple’s power structure. More authority is now flowing to a quartet of executives: Ternus, services chief Eddy Cue, software head Craig Federighi and new COO Sabih Khan. Apple’s AI efforts have been redistributed across its leadership, with Federighi becoming the company’s de facto AI chief.

Ternus is also poised to take a starring role next year in the celebration of Apple’s 50th anniversary, further raising his profile. And he’s been given more responsibility over robotics and smart glasses — two areas seen as future growth drivers. 

Further reorganization is likely. Deirdre O’Brien, head of retail and human resources, has been with Apple for more than 35 years, while marketing chief Greg Joswiak has spent four decades at the company. Apple has elevated the key lieutenants under both executives, preparing for their eventual retirements.

At the same time, Apple is contending with a talent drain in its engineering ranks. This has become a serious concern for the executive team, and Apple’s human resources organization has been instructed to ramp up recruitment and retention efforts, people familiar with the situation said.

Robby Walker, who had overseen Siri and an initiative to build a ChatGPT-like search experience, left the company in October. His replacement, Ke Yang, departed after only weeks in the job, joining Meta’s new Superintelligence Labs.

To help fill the void left by Giannandrea, Apple hired Google and Microsoft Corp. alum Amar Subramanya as vice president of artificial intelligence. He’ll report to Federighi, the software chief.

But there’s been a broader collapse within Apple’s artificial intelligence organization, spurred by the departure of AI models chief Ruoming Pang. Pang, along with colleagues such as Tom Gunter and Frank Chu, went to Meta, which has used eye-popping compensation packages to lure talent.

Roughly a dozen other top AI researchers have left the organization, which is suffering from low morale. The company’s increasing use of external AI technology, such as Google’s Gemini, has been a particular concern for employees working on large language models.

Apple’s AI robotics software team has also seen widespread departures, including its leader Jian Zhang, who likewise joined Meta. That group is tasked with creating underlying technology for products such as a tabletop robot and a mobile bot.

The hardware team for the tabletop device, code-named J595, has been bleeding talent too — with some headed to OpenAI. Dye also was a key figure overseeing that product’s software design.

Read More: Apple’s AI Push to Hinge on Robots, Security, Lifelike Siri

The user interface organization has been hit as well, with several team members leaving between 2023 and this year. That attrition culminated in Dye’s exit, which stemmed partly from a desire to integrate AI more deeply into products and a feeling that Apple hasn’t been keeping pace in the area. Another top interface leader under Dye, Billy Sorrentino, also left for Meta.

The hardware side of the design group — the team responsible for the physical look and feel of Apple’s products — has been nearly wiped out over the last half-decade. Many staffers followed former design chief Jony Ive to his studio, LoveFrom, or went to other companies.

Longtime interface designer Stephen Lemay is now stepping in as Dye’s replacement. Cook is also taking on more responsibility for overseeing design, a role that had been held by Williams.

Ive, a visionary designer who helped create the iPhone, iPad and Apple Watch, is now working with OpenAI to develop a new generation of AI-enhanced devices. That company acquired Ive’s startup, io, for more than $6 billion to jump-start its hardware business — setting its sights on Apple’s territory.

Like Meta, OpenAI has become a key beneficiary of Apple’s talent flight. The San Francisco-based company has hired dozens of Apple engineers across a wide range of fields, including people working on the iPhone, Mac, camera technology, silicon design, audio, watches and the Vision Pro headset. 

In a previously unreported development, the AI company is hiring Apple’s Cheng Chen, a senior director in charge of display technologies. His purview included the optics that go into the Vision Pro headset. OpenAI recruited Tang Tan, one of Apple’s top hardware engineering executives, two years ago.

Read More: Apple’s Star Designer Who Introduced iPhone Air Leaves Company

And over the summer, the company lost the dean of Apple University, the internal program designed to preserve the company’s culture and practices after the passing of co-founder Steve Jobs. Richard Locke, who spent nearly three years at Apple, left to become dean of the Massachusetts Institute of Technology’s business school.



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Epstein grand jury documents from Florida can be released by DOJ, judge rules

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A federal judge on Friday gave the Justice Department permission to release transcripts of a grand jury investigation into Jeffrey Epstein’s abuse of underage girls in Florida — a case that ultimately ended without any federal charges being filed against the millionaire sex offender.

U.S. District Judge Rodney Smith said a recently passed federal law ordering the release of records related to Epstein overrode the usual rules about grand jury secrecy.

The law signed in November by President Donald Trump compels the Justice Department, FBI and federal prosecutors to release later this month the vast troves of material they have amassed during investigations into Epstein that date back at least two decades.

Friday’s court ruling dealt with the earliest known federal inquiry.

In 2005, police in Palm Beach, Florida, where Epstein had a mansion, began interviewing teenage girls who told of being hired to give the financier sexualized massages. The FBI later joined the investigation.

Federal prosecutors in Florida prepared an indictment in 2007, but Epstein’s lawyers attacked the credibility of his accusers publicly while secretly negotiating a plea bargain that would let him avoid serious jail time.

In 2008, Epstein pleaded guilty to relatively minor state charges of soliciting prostitution from someone under age 18. He served most of his 18-month sentence in a work release program that let him spend his days in his office.

The U.S. attorney in Miami at the time, Alex Acosta, agreed not to prosecute Epstein on federal charges — a decision that outraged Epstein’s accusers. After the Miami Herald reexamined the unusual plea bargain in a series of stories in 2018, public outrage over Epstein’s light sentence led to Acosta’s resignation as Trump’s labor secretary.

A Justice Department report in 2020 found that Acosta exercised “poor judgment” in handling the investigation, but it also said he did not engage in professional misconduct.

A different federal prosecutor, in New York, brought a sex trafficking indictment against Epstein in 2019, mirroring some of the same allegations involving underage girls that had been the subject of the aborted investigation. Epstein killed himself while awaiting trial. His longtime confidant and ex-girlfriend, Ghislaine Maxwell, was then tried on similar charges, convicted and sentenced in 2022 to 20 years in prison.

Transcripts of the grand jury proceedings from the aborted federal case in Florida could shed more light on federal prosecutors’ decision not to go forward with it. Records related to state grand jury proceedings have already been made public.

When the documents will be released is unknown. The Justice Department asked the court to unseal them so they could be released with other records required to be disclosed under the Epstein Files Transparency Act. The Justice Department hasn’t set a timetable for when it plans to start releasing information, but the law set a deadline of Dec. 19.

The law also allows the Justice Department to withhold files that it says could jeopardize an active federal investigation. Files can also be withheld if they’re found to be classified or if they pertain to national defense or foreign policy.

One of the federal prosecutors on the Florida case did not answer a phone call Friday and the other declined to answer questions.

A judge had previously declined to release the grand jury records, citing the usual rules about grand jury secrecy, but Smith said the new federal law allowed public disclosure.

The Justice Department has separate requests pending for the release of grand jury records related to the sex trafficking cases against Epstein and Maxwell in New York. The judges in those matters have said they plan to rule expeditiously.

___

Sisak reported from New York.



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