By Vicky Ge Huang and Krystal Hur

Centralized, gated and closed on weekends, the New York Stock Exchange is the ultimate architectural symbol of everything bitcoin was created to disrupt. And yet, the 233-year-old titan of Wall Street has quietly positioned itself as an unlikely crypto powerhouse.

Between a multibillion-dollar blitz into digital assets and a planned 24/7 trading platform for blockchain-based securities, the storied exchange is undergoing its grandest -- and likely riskiest -- transformation yet: using the distributed ledger technology behind bitcoin to reinvent the very system it spent centuries building.

"We've been on the forefront of the evolution of markets from analog to electronic, and I think now we're seeing, a quarter-century later, the next wave of transition from electronic to digital," said Michael Blaugrund, vice president of strategic initiatives at Intercontinental Exchange, NYSE's owner.

He foresees a "highly probable future" where blockchain becomes a major venue for NYSE's core operations, such as trading, clearing, settlement, capital formation and data distribution, Blaugrund said.

That conviction, led by Intercontinental Exchange founder and Chief Executive Jeffrey Sprecher, paved the way for a roughly $200 million investment in the crypto exchange OKX in March , according to people familiar with the matter. The deal values OKX at $25 billion and comes a year after the China-founded exchange agreed to pay more than half a billion dollars to resolve a federal investigation.

The investment is part of a much broader movement on Wall Street to wade into risky bets that were previously seen as off limits, from prediction markets to crypto. The Trump administration's friendly regulatory stance toward nontraditional financial assets, as well as individual investors' demand for such audacious trades, have helped fuel the frenzy.

The stock exchange's bets on crypto come at a tough time for crypto bulls. Bitcoin just notched its worst start to the year since the first three months of 2018. Bitcoin recently traded around $75,000, well below its high of $126,273 hit in October on hopes that President Trump's financial ties to crypto and industry-friendly regulations would usher in a golden age for digital assets.

While such a selloff might have been a death knell in years past, it has done little to ease Wall Street's appetite for crypto. NYSE rival Nasdaq said last month that it was partnering with crypto exchange Kraken and other companies to develop its plan to offer tokenized stocks on its exchange. Big banks, including JPMorgan Chase and Bank of America, are weighing whether to launch their own stablecoins.

In December, Sprecher and OKX founder Star Xu met at a French restaurant in London. The two founders hit it off based on their shared product-engineering backgrounds and similar low-profile personalities, according to Haider Rafique, global managing partner at OKX, who was also present at the dinner.

Later this year, Intercontinental Exchange, or ICE, will license OKX's spot crypto prices and launch U.S.-regulated futures contracts tied to them. Pending regulatory approval, OKX will offer its more than 120 million global customers access to ICE's U.S. futures and NYSE's tokenized equities, a key step in the exchange's plan to issue securities that are represented as digital tokens on a blockchain.

NYSE recently announced that it has partnered with Securitize to develop a tokenized securities platform that would offer 24/7 trading and settle trades instantly. Investors would also be able to use stablecoins -- a type of cryptocurrency typically pegged to the U.S. dollar -- to fund trades.

NYSE has extended its crypto investments to prediction markets, the fast-growing industry allowing users to make yes-or-no wagers on topics from politics to sports. In October, ICE agreed to invest up to $2 billion in Polymarket, boosting the blockchain-based prediction-markets exchange's value to $9 billion.

The seemingly unlikely deal was born out of shared experiences with Federal Bureau of Investigation raids. On Nov. 13, 2024, FBI agents woke Polymarket founder Shayne Coplan at his Manhattan home and seized his phone as part of an investigation into whether the platform was illegally allowing U.S. users to trade on the site.

Sprecher reached out to Coplan after the Justice Department dropped its probe. In an interview with CNBC, Sprecher said Coplan "was falsely accused of wrongdoing and was raided by the FBI," an experience that he said he suffered a few years earlier.

"I'm old and bald. He's young and mopheaded. I have a closet full of ties. I don't think he owns a tie," said Sprecher from the NYSE trading floor. "The company that we're sitting in was started in 1792. He's got the hottest financial services company in 2025."

Like crypto firms, prediction markets have faced controversy during their ascent. The Trump administration and states are locked in a battle over whether event-based contracts, especially those tied to sports, are the same as online betting and should be regulated as such.

NYSE has backed away from the controversy, with Sprecher stating that the stock exchange's interests lie in bets tied to other topics such as weather and corporate events.

"Good for Polymarket if they can navigate the sports complex -- kind of not high on our list in terms of what we're going to contribute to them and what they'll contribute to us," said Sprecher on an October earnings call.

The wager on prediction markets isn't the first time that NYSE made an early bet on a nascent and controversial industry: In January 2015, NYSE made a minority investment in Coinbase, when bitcoin was still a fringe asset trading at around $300, and made $900 million after selling its stake in 2021.

Not all of NYSE's crypto investments have paid off. A stark reminder is Bakkt, which was launched in 2018 by ICE with the goal of offering physically settled bitcoin futures. Since then, the company's business model has shifted restlessly, from a retail loyalty-points app to a technical-infrastructure play. By 2023, ICE had written down its stake in Bakkt by more than $1 billion. And in 2024, the stock faced delisting warnings from the NYSE.

Today, the company is attempting to rebuild as an artificial-intelligence-driven infrastructure platform, though it remains strained by the loss of Webull, a client that accounted for 74% of the company's crypto revenue in 2024.

"That remains a show me story, and is likely to remain one until we begin to see a significant roster of partnerships formed and announced," said Mark Palmer, an analyst at Benchmark, of Bakkt's latest pivot.

Write to Vicky Ge Huang at vicky.huang@wsj.com and Krystal Hur at krystal.hur@wsj.com

(END) Dow Jones Newswires

April 16, 2026 20:00 ET (00:00 GMT)

Copyright (c) 2026 Dow Jones & Company, Inc.