Jamie Dimon's $60 Million Bet on Bank One Launched Remarkable Second Act

In 1998, Jamie Dimon, a rising star on Wall Street, was unexpectedly fired from Citigroup, a move that shook both his professional and personal life. Dimon, who had helped build the financial conglomerate alongside his mentor Sandy Weill, found himself at a crossroads. He recalls the shock of the firing and the subsequent questions from his children about the family’s future. Dimon spent the next 18 months considering his next steps, exploring various options including teaching, starting his own merchant bank, and even retirement. During this period, he kept an open mind and reached out to various connections, one of which led to a meeting with Jeff Bezos, the founder of Amazon.

Dimon and Bezos had a particularly consequential conversation. Bezos was seeking a president for his fast-growing company, and the two hit it off, becoming friends ever since. However, Dimon saw the move to Seattle and the transition to the tech world as a bridge too far. He joked about the radical change in lifestyle, saying it would be like stepping into an alternate universe. Amazon, at that time, was a much different proposition from the $2.4 trillion colossus it is today, with a share price of less than a dollar and a market cap of just $5.5 billion at the end of 2000.

After the Amazon visit, Dimon considered other positions, including running global investment banks and insurance giant AIG. Another offer he declined was from Home Depot, a company he had never actually stepped foot in before. However, what stuck was a headhunter’s call about Bank One—a large but beleaguered Chicago bank. 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. Analyst Mike Mayo had a great line at the time about the bank’s problems: “Even Hercules couldn’t fix it.”

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 “all in.”

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.

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.