By LUKE KENTON, US SENIOR REPORTER
Published: 23:25 EDT, 25 August 2025 | Updated: 23:25 EDT, 25 August 2025
The Rooney family has long been considered one of the NFL's most enduring dynasties, credited with shaping the Pittsburgh Steelers into a model franchise of stability and success.
But their foundations were rocked this week by the sudden and mysterious death of an heir in the Hamptons.
Matthew 'Dutch' Rooney, grandson of legendary Steelers founder Art Rooney Sr., was found dead at his $3.4million mansion in East Hampton, New York, on August 15. A cause of death for the 51-year-old has not been released.
Friends and loved ones have paid tribute to the writer, artist and patron of the arts, with an online obituary hailing him as 'one of life's last true Dandies and an authentic Bon Vivant.'
Rooney served as the vice chair of the donor arm of the New York City Ballet's Allegro Circle and was on the board for the Metropolitan Opera of New York.
His death is the second tragedy to strike the Rooney family in less than two months. In early July, Tim Rooney Sr., a former Steelers part-owner and renowned NFL scout, died aged 84 after a brief battle with cancer.
The back-to-back losses have turned fresh attention on the Rooney legacy - a dynasty that looms large not only in the NFL record books but also in American culture.
The Rooneys are revered in football as the family that transformed the Steelers into six-time Super Bowl champions, and they also boast Hollywood connections, counting actor sisters Rooney Mara and Kate Mara among their descendants.
Yet behind that polished legacy lies a murkier origin story.
Matthew 'Dutch ' Rooney was founded dead in his East Hampton home last Friday. He was just 51
Matthew is the grandson of legendary Pittsburgh Steelers founder, Art Rooney Sr.
For decades, Art Rooney Sr. was dogged by whispers that his fortune was not built on the pluck and hard work he often claimed.
The tale he told was that of a former athlete who hit it big on horse racing, invested shrewdly in the stock market, and made his early living promoting boxing bouts across the Steel City.
But FBI files and archival research reveal he was deeply embedded in Pittsburgh's underground economy during Prohibition - running numbers, bootleg beer operations, off-track betting, gambling dens, slot machines, and striking backroom deals with the mob.
Rooney's first known foray into the underworld came during Prohibition, when he and his partners took over a struggling brewery in Braddock, just outside of Pittsburgh, the Post-Gazette reported in 2022.
Reorganized as the Home Beverage Company, the plant was raided twice in the 1920s by federal authorities tipped off to an illegal beer racket. In 1927, agents scaled a 10-foot fence to break into the plant after hours, where they found workers rolling out barrels of high-alcohol beer ready to ship.
When confronted with the evidence, Rooney and his co-owners played dumb. They claimed they had no idea the illegal beer was being brewed under their noses, but court records show their assertions of ignorance were dismissed as 'not worthy of belief.'
Though criminal charges never reached Rooney directly, they marked the first time his name was publicly linked with illicit trade.
When Prohibition ended in 1933, and the US was still reeling from the Great Depression, Rooney tried to restart the brewery under the banner of 'Rooney's Famous Beer', but by 1937, the plant was bust and forced into a sheriff's sale to cover mounting debts.
Just two weeks later, Rooney Sr. suddenly struck it rich - claiming he hit a once-in-a-lifetime, three-day hot streak at the racetrack, a story that would become known as 'Rooney's Ride' and serve as the enduring myth of how he bought the Steelers.
Rooney (center) carved out his own path away from football, becoming a writer, artist and prominent supporter of New York¿s ballet and opera scene
He was discovered dead at his $3.4M Hamptons home, but the cause of death has not been revealed
Art Rooney claimed to have made his fortune through honest means and gambling luck - but FBI files released decades later told a different story
The story Rooney liked to tell was that in the summer of 1937, he walked into Saratoga Race Course in New York with just a few hundred dollars in his pocket and walked out nearly half a million dollars richer.
He claimed to have parlayed the winnings into the purchase of the Pittsburgh Steelers - then known as the Pirates - securing his place in football history with little more than a gambler's good fortune.
It was a tale that fit neatly with his public persona - the charming, grinning, cigar-chomping Irishman who invoked the luck of his forebears to achieve the American dream. But historians and FBI files have long cast doubt on whether the legendary 'Rooney's Ride' was ever really the full story.
In 1933, deep into the Great Depression, Rooney personally loaned his father $130,000 - equivalent to around $3 million today - to relaunch the family's failed brewery that had shuttered six years earlier.
The six-figure sum, on hand during the worst economic collapse in US history, signals that Rooney had access to vast wealth long before his storied gambling streak - likely amassed through earlier, discreet rackets.
In fact, decades later, it would be discovered that in the late 1920s and early '30s, he partnered with local promoter and mob-affiliate Milton Jaffe to operate the Show Boat - a floating speakeasy and casino moored on the Allegheny River.
The boat was raided in 1930, with federal agents seizing roulette wheels, slot machines, and liquor. Jaffe and the casino's manager were both arrested.
Rooney himself was never charged, and his role as a silent backer remained hidden from the public for decades. His involvement was only confirmed years later by his brother Jim and, eventually, by his son Art Jr. in a memoir.
Actor sisters Rooney Mara and Kate Mara are great-granddaughters of Art Rooney on their mother's side. They are also great-granddaughters on their father’s side of Wellington Mara, the longtime co-owner of the New York Giants
The tale he told about how he got his wealth was that of a former athlete who hit it big on horse racing, invested shrewdly, and made his early living promoting boxing bouts
The serial entrepreneur also carved out a lucrative foothold in Pittsburgh's 'numbers' racket, a term referring to the illegal street lottery that flourished across the city's neighborhoods for decades.
In FBI interviews from the 1950s unearthed by the Post-Gazette, Rooney is described to agents as one of the men who secretly 'ran the games', while using front men - including his own brother Jim - to shield his involvement whenever the feds came knocking.
But Rooney's biggest earner came through slot machines. By the early 1940s, Rooney and his longtime business partner, Barney McGinley, were illegally distributing thousands of slot machines through a shell company called Penn Mint Service.
At the time, all mechanical gambling devices were outlawed in the state. In an attempt to skirt the laws, Rooney's machines were designed under the pretense of legality: instead of coins, the machines dispensed mints or tokens that could instantly be converted into cash.
The illicit operation was a winning money-spinner, raking in enormous profits. And according to FBI files, Rooney's racket was run in tandem with Pittsburgh's mob.
Informants told federal agents that Rooney struck territorial deals with Pittsburgh crime family boss John LaRocca and the infamous Mannarino brothers, Sam and Kelly, dividing up machine placements across the city between them, with Rooney taking areas north of the Allegheny.
By the close of the 1940s, local newspapers were openly describing two 'widely known' men as the kingpins of Pittsburgh's underground slot machine trade - a thinly veiled reference to Rooney and McGinley, reported the Post-Gazette.
Rooney had amassed numerous close political connections and wielded considerable influence over local police.
Informants told federal agents that Rooney struck territorial deals with Pittsburgh crime family boss John LaRocca
Pittsburgh crime family boss John LaRocca
The serial entrepreneur also carved out a lucrative foothold in Pittsburgh’s ‘numbers’ racket, a term referring to the illegal street lottery that flourished across the city, according to the FBI
FBI files from the 1940s and '50s described Rooney's slot machine empire as indistinguishable from the way the mob ran its rackets, with territorial agreements, profit-sharing, and use of intimidation to protect placements.
The only thing that distinguishes Rooney from his mobster peers is the fact that he apparently never used violence or the threat of violence to run his operation.
Rooney ran his illicit ventures more like a citywide syndicate than a street‑mob, the Post-Gazette reported.
For all of his life, Rooney denied publicly that he was ever involved in unlawful practices, only admitting that he knew others who were.
'I touched all the bases,' Rooney once quipped when asked if he knew his fair share of crooks.
He died in 1988. In the decades that followed, FBI files connected to mob investigations began being disclosed publicly, revealing the stunning truth.
Despite the evidence, family members have offered only partial acknowledgments to the allegations made in the files.
His brother, Jim, admitted in the 1980s that Rooney had been involved in the Show Boat, and his namesake son later confirmed it in his 2008 memoir.
But Dan Rooney, who succeeded his father as Steelers president, stuck firmly to the official family line, insisting he had 'no knowledge' of any mob ties or illegal rackets.
FBI files from the 1940s–50s described Rooney’s slot machine empire as indistinguishable from the way the mob ran its rackets - except he didn't use violence
Pittsburgh Steelers owner Art Rooney II looks on before a game against the Cleveland Browns (2021)
One thing that cannot be disputed is the incredible empire Rooney left behind.
Under his leadership, the Pittsburgh Steelers became the stuff of NFL legend, and the Rooneys became football royalty.
And despite the whispers of his shady dealings, Rooney cultivated a reputation as one of the most beloved figures in professional sports. He was known for treating players, staff, and fans with a warmth that set him apart from other owners.
Often, he could be found shaking hands or handing out prayer cards in the stands.
To Pittsburgh, Rooney was 'The Chief,' the smiling patriarch who embodied the city's values. He lived out his final years as a community pillar, and his impact on the NFL can still be felt today.
Now, nearly a century after Art Rooney Sr. laid those foundations, the dynasty he created is once again under the spotlight - not for triumph this time, but for tragedy.
The sudden, unexplained death of his grandson Matthew in the Hamptons, following so soon after the passing of longtime scout and part-owner Tim Rooney Sr., has cast a somber shadow over football's most enduring family.