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[NEW YORK] Rob Granieri took to the dance floor with long hair flowing from his fedora, shiny jacket glinting and a boutonnière bursting with colour.

The wealthy recluse showed off his moves after platters of paddlefish caviar and bacon-wrapped shrimp swirled through the room to celebrate his Scarlet Pearl, the casino hulking over Mississippi’s brackish Biloxi Bay. The disco-bright veneer gave the revellers no hint of the 53-year-old billionaire’s hidden reality.

Far away from slot machines and roulette, this is the man piling up billions of US dollars as the last founder standing at Jane Street, the black-box money machine minting Wall Street records. Even LuAnn Pappas, his pick to run the casino, said that there have been moments when it was hard to believe Granieri is perched atop what’s now the world’s most lucrative trading house.

“I sat down with a guy who had hair down to his waist in a ponytail and a backpack on,” Pappas said, recalling her first meeting with him. “Someone you’d expect to see on a park bench reading Shakespeare.”

At his day job in downtown Manhattan, the casino of capitalism, Granieri slips back into the schlubby wardrobe that’s the norm at the 25-year-old firm. The soft-spoken libertarian guards his low-key stature so much that he often goes unrecognised within the company, where he officially has no title. His profile in the employee directory stands out because of its missing headshot.

Those who know Granieri describe him as a shy introvert with a “golly gee” attitude who easily recedes into the background. While Wall Street frolics in the Hamptons, he prefers revelling in anonymity at Burning Man, the mecca of counterculture. His rare casino getaways also let him cut loose unnoticed, like he did last year.

“I wouldn’t recognise him walking down a street,” said Alphacution’s Paul Rowady, a researcher who digs into firms such as Jane Street. “Congratulations to Rob Granieri: Influence and anonymity is a very rare combination.”

But this year is different. The firm’s cherished obscurity has been shredded, nudging Granieri closer to the thing he most detests, the spotlight.

Legal wrangles and ballooning profits have drawn global attention. Rivals are swapping notes on Jane Street, piecing together a portrait of a firm that notched US$10.1 billion of trading revenue in the second quarter, trouncing the biggest banks. Its haul for the year’s first half eclipsed US$17 billion, almost on par with its full-year record set in 2024.

This account of Granieri is based on more than a dozen sources with knowledge of the firm’s operations or its co-founder, many of whom asked not to be identified because they are not authorised to speak publicly. A representative for Granieri declined to comment.

A year ago, the firm was best known as the launchpad of Sam Bankman-Fried, who went on to become a crypto wunderkind before ending up in prison.

But then came Jane Street’s bruising legal battle with a pair of departing traders. When the firm sued them last year for allegedly stealing an “immensely valuable” strategy, it drew attention from an Indian regulator, which accused the company of rigging the world’s largest options market. The firm has vowed to fight those claims.

By then, Granieri was already facing his own embarrassment over being duped into funding a plot for a military coup in Africa.

The events have been a jarring experience for the firm’s army of mathematicians and engineers, who are more comfortable geeking out over bughouse chess and mining anomalies in markets to get rich.

In the past, management’s main anxiety was keeping a lid on executives’ swelling wealth.

In 2018, a senior Jane Street partner violated that protocol by arranging for Cardi B to perform at his son’s bar mitzvah in New York’s trendy TAO Downtown. The hiring of a Grammy-winning rapper for a teenager’s coming-of-age ritual was frowned upon at a firm that eschews the industry’s penchant for emblazoned vests as too fratty.

Granieri and his lieutenants spent weeks trying to suppress any detail of the party getting out.

Unlike his peers who snap up trophy homes, Granieri has long preferred to live in rental housing to avoid the headaches of owning property. Still, a landlord once took him to court after Granieri missed reminders for an unpaid US$10,372 bill.

One of his few personal indulgences is fine dining. A colleague recalled that when Granieri was asked why he did not cook at home, he joked: Why do that when he can eat at Le Bernardin every night.

Chateau Granieri

Granieri grew up just outside Norristown, Pennsylvania, an old mill town that was a key stop on the Underground Railroad.

Residents are at a loss to explain his exploits just 161 km away. When local historian Janice Boyer looked into the trading house he built, the first description she saw was a “top Wall Street firm no one’s heard of”.

“Well, they are right about that,” she said. “It’s nice to know a local boy does well.”

For longtimers, the best known connection to the family is his parents’ former business, a once-popular banquet hall called Chateau Granieri.

According to his high school yearbook, Granieri showed a fondness for Metallica and “talks with radicals and libertarians”. He also harboured ambitions to make a lot of money.

After graduating from the University of Pennsylvania in 1992, he turned down an opening at a New Jersey operation that wanted him to cold-call people to pitch stocks.

With no other offers, he printed a stack of resumes and dropped them off on each floor of Philadelphia’s tallest buildings. That’s how he scored a job at Jeff Yass’s Susquehanna International Group, the quant-trading firm that was quietly becoming a market behemoth.

By the time Granieri quit at 27, he was pulling in US$700,000 a year and itching for change. He bonded with a colleague, Mike Jenkins, over their mutual dislike for a middle manager. The pair, along with another trader, Tim Reynolds, set out in 1999 to build what would become Jane Street.

Susquehanna sued them, claiming they had filled out their bench by poaching top talent who happened to be armed with its proprietary information, breaching non-compete agreements. In the midst of the case, Yass approached Granieri at a gathering and talked with him like nothing was wrong. When Granieri reminded him they were battling in court, Yass shrugged and said that’s just business. The docket shows the case later went dormant.

The allegations bear similarities to Jane Street’s lawsuit last year against two traders who bolted for Izzy Englander’s Millennium Management – the case that ended up triggering the probe in India.

Pot-bellied pig

Jane Street, Citadel Securities and Hudson River Trading are part of a rising class of market-making firms that have built expansive high-speed systems to carry out investor trades, benefiting from electronification and the rapid growth of exchange-traded funds.

Jane Street alone accounted for 24 per cent of all US-listed primary ETF trading volume in 2024. It handles over 90,000 products across more than 240 exchanges, filling voids left as stricter capital rules led investment banks to pull back.

It has found a lucrative niche in capturing brief mismatches in prices between plain-vanilla assets and their derivatives. And its profits are soaring above the pack, boosted by proprietary trading with its own capital – a stockpile that has grown to US$53 billion. By the second quarter, the pace of revenue had quickened so dramatically that the firm earned in two weeks what took all year a decade ago.

Jane Street’s other co-founders did not stick around to see that explosive growth.

Marc Gerstein, an IBM developer who was the fourth member of the founding group and a diehard New York Mets fan, was one of the earliest departures.

Reynolds followed. Surviving a car crash after Jane Street’s first holiday party, he remained a crucial presence in the early years. But by 2012, he left to build art schools and launched a brand of luxe, ultra-private resorts in idyllic locales.

Jenkins, who worked on a nuclear submarine, was known for his collection of war memorabilia scattered around the office. After his departure, he earned a reputation for donating to influence New York City elections and walking a pet pot-bellied pig, Queelin, around Manhattan’s Tompkins Square Park.

‘Money in the hat’

Granieri has zealously sought to preserve Jane Street’s invisibility as long as possible. After the firm scored big by betting against its own bank in the 2008 financial crisis, he fumed when a 20-something trader was publicly quoted exuding confidence that his job was secure.

Inside the office, Granieri is even better known for his work habits, staying online to odd hours, avoiding lengthy vacations and maintaining his unkempt style.

That embodies the firm’s culture. One Jane Street veteran described times when he had to shepherd a colleague to Brookfield Place, the shopping mall near the firm’s headquarters, to buy a proper outfit ahead of a client meeting.

The firm is insular, and its office is an island of surplus. In addition to in-house chefs, there are rooms for poker, video games and an original war-era Enigma machine that was procured off eBay in Italy.

Staff bet on everything. Co-workers wager on coin tosses or how much weight a colleague can gain in an hour by eating watermelon. Then there’s “Money in the Hat”: Employees toss cash and slips of paper into a hat that travels around the office before a lucky name is drawn.

Such ambient gambling can veer into fraternity-like vulgarity. At one outing, employees made markets on who would go home with a female colleague, according to two former staffers who were present.

Granieri once sent out a note, warning against certain inappropriate workplace relationships with a specific addendum: “Don’t make the situation worse by talking about it, making jokes, placing bets.”

He’s one of the few people who can speak with that authority at a company that swears it’s governed not by top-down leadership but by the mutual consent of dozens of partners.

When a staffer tried to get a signature on an administrative form, nobody on his desk was willing, reacting allergically to the idea that they were in charge. The only person they agreed had authority was Granieri, who took care of it.

Granieri has sought to leave his imprint beyond the firm by giving away wealth. A more strident vision of such philanthropy – known as effective altruism and practiced by some of the early Jane Street leaders – was what attracted Bankman-Fried to join the company.

Granieri’s giving spans prominent causes and niche endeavours, including donations to psychedelic studies. His gifts often come with a rider requesting anonymity.

Causes include an initiative to end mass incarceration in the US and an education movement focused on rooting out “activists imposing harmful agendas” in schools. When the Taliban retook control of Afghanistan, he funded an effort to privately extract locals at risk.

“He is probably the most generous donor for causes of freedom in the world,” said Garry Kasparov, the chess champion who used to chair the Human Rights Foundation.

African coup

Despite his Wall Street prowess, Granieri has seen a variety of personal projects go awry – such as the time Kasparov opened the door for Granieri’s multimillion-dollar donation to a plot to overthrow the government of South Sudan.

The chess maestro connected the financier with Peter Ajak, a Harvard fellow and activist, who was later criminally accused of gathering cash for a plot to buy AK-47s, Stinger missiles and grenades. Ajak and an associate pleaded guilty to breaking US weapons-export laws and admitted the aim was to overthrow South Sudan’s government. Granieri was not accused of wrongdoing.

“The person Rob thought was a human rights activist defrauded Rob and lied about his intentions,” said Dan Koffmann, his attorney at Quinn Emanuel.

Granieri also invested in Kentucky coal mines through an entity that was managed by a former derivatives trader. A co-investor later sued that person for allegedly cheating them out of valuable business opportunities.

Frankie the fish

And then there was a more comical mishap at the Scarlet Pearl, when Granieri said he was conned by a former nun.

Granieri backed her project at the urging of a close family friend. But as disagreements arose, a team of private investigators told him she had already been sued almost 60 times. He sued too, accusing her of lavish spending and questionable decisions that included recruiting a convicted felon who went by Frankie the Fish. (When reached for comment, Frankie the Fish said he never met Granieri.)

While Granieri prevailed in that lawsuit, a judge chided him, noting the financier had waited until deep into the process to do “the type of due diligence he should have conducted at the outset.”

Granieri tried to persuade other Wall Streeters to buy into the casino. But talks with the likes of billionaire Carl Icahn did not yield a deal because Granieri “viewed his terms as too onerous”, a court record shows. So Granieri poured in more money, creating a thriving casino resort in D’Iberville, Mississippi.

With his backing, the Scarlet Pearl has scored points in gambling circles for its willingness to take risks.

It took punter Jim “Mattress Mack” McIngvale’s US$3.5 million bet on the World Series in 2019. “We are in the gambling business,” Granieri told Scarlet Pearl managers terrified that losing would burn a hole in their budget.

The gamble paid off for the house, but only just: The Houston Astros lost to the Washington Nationals in the final game of the series.

Pappas, the Scarlet Pearl’s CEO, said that the billionaire is beloved there for his humility. But she recalled her reaction when she first learned of his passion for Burning Man. “I was shocked,” she said. “It was like the hippie movement. You don’t shower for days. He gets animated when he talks about Burning Man.”

He started making regular jaunts to the fiesta in the Nevada desert a little over a decade ago, introduced by friends in New York’s performing arts scene. One artist collective later credited him with helping build a popular attraction – a geodesic dome filled with yoga balls. At night, the site beckoned burners to prance about by the warm glow of its neon sign: “Balls Deep.”

But this year, Granieri skipped the trip.

As Burning Man approached in August, Jane Street faced a deadline to respond to India’s regulator. And Manhattan’s trading houses were busy, with analysts predicting another bumper haul for trading firms.

The question is whether Jane Street notched yet another record or finally tapped the brakes with the world watching closely. Staying the course would require embracing the cheesy tagline of the new John Travolta movie filmed at his casino: “Everything on the line. Nothing off the table.” BLOOMBERG