Jerry Wolman, a onetime Washington paint-store clerk who built and quickly lost one of the country’s biggest real estate fortunes of the 1960s, a collapse that ended his ownership of the world’s second-tallest skyscraper, the Philadelphia Eagles football franchise and the Philadelphia Flyers hockey team, died Aug. 6 at his home in Potomac. He was believed to be 86.

He had sepsis and a kidney ailment, said his sister, Sandy Teplin.

Mr. Wolman, a high school dropout, grew up in the Pennsylvania coal country as the son of an immigrant produce salesman. After Merchant Marine duty in World War II, he settled in Washington and worked in a paint store, where he met contractors who were prospering in the postwar housing boom.

From there, it was a rapid jolt from obscurity. Mr. Wolman built an estimated 25,000 homes and apartment units, which propelled him to the front rank of real estate barons. By 35, he was worth as many millions of dollars on paper. He was dubbed a “boy wonder of the construction industry.”

He opened offices in Chicago and Philadelphia and became involved with construction projects of ambitious scale and design.

Jerry Wolman built an estimated 25,000 homes and apartment units, which propelled him to the front rank of real estate barons. By 35, he was worth as many millions on paper. He was dubbed a “boy wonder of the construction industry.” (Tom Kelley/The Washington Post)

The most monumental venture was the 100-story, steel-and-glass John Hancock Center in Chicago, which Mr. Wolman described as a “city in the sky” for its housing and office components. When told of the opportunity to build on the North Michigan Avenue site in 1964, Mr. Wolman said he bought the land for $6 million within 15 minutes of the offer. The building was named for the insurance company that provided the mortgage.

Mr. Wolman also bought Philadelphia’s old Connie Mack Stadium and built the Spectrum arena in Philadelphia as part of a successful lobbying effort to secure the Flyers for the city in the late 1960s.

His most beloved property was the Eagles, for which he paid a $5.5 million stake in 1963 to become majority owner in his mid-30s — the youngest of a National Football League franchise.

Mr. Wolman often recounted how, as a young man, he had hitchhiked 100 miles from his home town to see the team play. Now, with deep pockets as a developer, he spoke of the responsibility to make the team great.

He spent lavishly on the Eagles’ marching band and hired Joe Kuharich, formerly the head coach with the Washington Redskins and the University of Notre Dame, as general manager and coach, signing him to a jaw-dropping 15-year contract worth $900,000.

Kuharich made a series of unpopular decisions, trading some of the team’s best players. Most notably, he swapped future Hall of Fame quarterback Sonny Jurgensen for the Redskins’ Norm Snead. Kuharich had only one winning season in five years, and the Eagles finished with a dismal 2-12 record in 1968, tied for worst in the NFL.

Fans held placards and wore buttons reading “Joe Must Go.”

Explaining his decision to keep Kuharich, Mr. Wolman later told the Philadelphia Inquirer: “I really liked the guy, and I was loyal to him. I knew his coaching days were probably over, but I wanted him to stay with the team. He knew that in a year or so I was going to move him upstairs.”

Amid a series of dramatic financial reversals, Mr. Wolman did not have the time to complete his plans for the Eagles. A crunch in the mortgage market in 1966 had a debilitating effect on his estimated $100 million fortune. He found himself vastly overextended and began selling off his holdings.

An engineering miscalculation with the foundation of the Hancock Center made Mr. Wolman’s financial situation dire. He spent millions of dollars of his own cash and credit lines to guarantee the project but ended up selling his interest in the building for a reported $5 million loss.

John Hancock took over the project, which was completed in 1968 for $95 million. Dubbed “Big John,” it was the world’s tallest building outside New York City. Only the Empire State Building, at 102 stories, reached higher.

Mr. Wolman endured further legal threats from hundreds of other creditors and subcontractors and reportedly was $72 million in debt. He filed for bankruptcy in 1968 and sold his interest in the Flyers.

Mr. Wolman vowed to keep the Eagles, but a Baltimore bankruptcy judge forced the sale. Trucking magnate Leonard Tose bought the team in 1969 for $16.1 million, a record amount for a professional sports franchise. Tose immediately fired Kuharich and bought out the remaining 10 years of his contract.

One of Mr. Wolman’s lesser-known legacies in the NFL was in persuading other team owners to finance NFL Films in the mid-1960s. He also provided the sports documentarians — whose shows helped bring cinematic flair to NFL coverage — with virtually rent-free property for a while in an old telephone-company building.

“Jerry Wolman’s a real unsung hero of NFL Films,” Steve Sabol, whose father founded NFL Films, told the Inquirer in 2009.

Jerry Wolman was born in Shenandoah, Pa., on Feb. 13 in 1926 or 1927; his family said that, as the fourth of nine children, record-keeping was less than fastidious. He usually used 1927 as his year of birth. His parents were Jewish immigrants from Eastern Europe, and his father eventually built a fruit stand into a wholesale fruit and produce business.

Mr. Wolman left school when he was about 15 to help support the family after his father died from a stroke. (Decades later, amid his rise in business, his high school gave him a diploma.)

Time magazine reported that Mr. Wolman and a brother opened a grocery store in Pennsylvania in 1949 but that, when they could not pay $5,000 in bills, Mr. Wolman and his wife left town in their 1938 Chevrolet, issuing promissory notes to creditors. They wound up in Washington and slowly paid back their debts, partly through Mr. Wolman’s job in a paint store.

The development business was equally rocky, at first. After some lucrative sales on his first few properties, Mr. Wolman lost all his savings on a group of Fairfax County ranch houses. He later persuaded his creditors to give him another chance, and he gradually recovered his money and began the foundation of his short-lived empire.

His first wife, Anne Unterberger, died at 41, in 1971, after a heart attack. Besides his sister, survivors include his wife of 29 years, Barbara Smith “Bobbie” Wolman of Potomac; two children from his first marriage, Alan Wolman of Englewood, N.J., and Helene Sacks of Potomac; a brother; and seven grandchildren.

After his bankruptcy, Mr. Wolman returned to development on a smaller scale and owned a bottled-water company for many years. In 1998, he was part of a group bidding to buy the Washington Redskins and what is now FedEx Field for a reported $600 million. He lost out to businessman Daniel M. Snyder, who paid $800 million.

In recent years, Mr. Wolman penned a memoir, “Jerry Wolman: The World’s Richest Man,” co-written by Richard and Joseph Bockol. In promoting the book, he spoke to community groups and schoolchildren about positive life lessons.

But when one youngster asked about a rival of the Eagles, Mr. Wolman could not help himself. “It’s not good to hate,” he said, “but I hate the Dallas Cowboys.”