After Success His Entire Career, Robert Sillerman’s Final Years Were Marked by Pain, Loss and Deception

Robert F.X. Sillerman became one of the most intriguing and wealthiest men in music by twice betting on his vision for the future of mass media. He made billions of dollars in two huge sales, but died in bankruptcy, pursued by the government and suffering the painful complications of a decade of throat cancer, eating out of a feeding tube and finding it increasingly difficult to breathe. He passed away in his sleep on Sunday at the age of 71.

He also carried heavy personal pain after the suicide of his 18-year-old daughter Mackinley in 2012, losing his only child in the home he shared with his wife Laura Baudo Sillerman. The founder of SFX Entertainment rarely spoke about the impact of his daughter’s death but his friends say it weighed on him and changed his outlook. In the years following that tragic 2012 event, he was often treated as a cartoon villain in the media, trying for a third, fourth and even fifth act in business, and some say the death of his daughter hardened him to any criticism. 

“He just didn’t a f— about anything,” said one former business partner who did not want to share their name. “Even when he was being sued in the end and was broke, hacking and wheezing with a hole in his throat and eating through a feeding tube, he was cracking blowjob jokes and talking about how he was going to ‘f this guy’ and how this other guy was a scumbag.”

Sillerman is largely responsible for helping create two of the biggest companies in music — iHeartRadio and Live Nation — through a series of deals he finalized in the late 1990s. He bankrolled Mel Brooks‘ Broadway production of The Producers and was golf partners with NBA legend Michael Jordan.

“He’s probably smartest person I’ve ever met,” said Shelly Finkel, a longtime boxing and music manager who co-founded SFX with Sillerman in 2011. “It’s sad how things ended because he really was a bright guy, but in the end he carried a lot of pain. I don’t want to say anything negative about someone who was good to me, but there were a lot of issues.”

In 2011, he tried to replicate his past success by capitalizing on the dance music craze, consolidating the EDM business into what he hoped would be a Live Nation-style powerhouse. But instead of a billion-dollar acquistion, Sillerman wiped out hundreds of millions in investor money and eventually had to file for bankruptcy. Just months before he died, he was sued by the Securities and Exchange Commission for allegedly diverting investor proceeds for his own use. 

Robert Francis Xavier Sillerman was born on April 12, 1948, in the Bronx neighborhood of Riverdale in a “very typical, liberal, educated Jewish household,” according to the 2011 book Ticket Masters: The Rise of the Concert Industry and How the Public Got Scalped by Dean Budnick and Josh Baron, which secured an interview with Sillerman. His father Michael created Keystone Radio Network and syndicated the popular show Lassie, but went bankrupt in 1961 and passed away in 1980, according to the book,

Sillerman graduated from Brandeis University in 1969, avoided the Vietnam War draft due to an injury and eventually went on to buy 92.7 WALL-FM in Middletown, New York, with famed DJ Bruce “Cousin Brucie” Morrow, according to Ticket Masters. 

“You and I buy a couple loaves of bread, Bob buys the bakery,” Morrow told Budnick and Baron of Sillerman’s sales abilities, which by 1988, netted nearly $1 billion value in broadcast assets. As his radio empire grew, Sillerman increasingly came up against Federal Communications Commission regulations restricting his ability to own multiple public broadcast stations, until 1996 and the passage of the Telecommunications Act, which lifted the restriction on owning multiple radio and television stations in a single market, paving the way for Sillerman’s firm to merge with Command Communications and become SFX Broadcasting. SFX grew into the nation’s seventh-largest chain and sold its 71 radio stations for $2.1 billion in 1998. The company that emerged would become Clear Channel, which is now known as iHeartRadio.

He followed the 1998 sale with a Feb. 29, 2000, deal that Playbill called “a quantum leap on the first Leap Day of the century,” selling his concert and theatrical production firm SFX Entertainment to Clear Channel for $3.2 billion. That business was built from a spree of acquisitions from 1997 to 2000 when Sillerman bought up Houston outfit Pace Concerts, New York promoter Delsener/Slater enterprises, Boston big man Don Law’s Blackstone Entertainment, Los Angeles’ Avalon Attractions, Jack Boyle’s Cellar Door International, Bill Graham Presents in Northern California and Jimmy Koplick’s 4,800-seat Oakdale Theater in Wallingford, Connecticut. 

While Sillerman’s buying spree made sense to few of the sellers in the later ’90s, the dots quickly connected by the time he sold the business. Clear Channel would later spin off its concert holdings into Live Nation in 2005 with CEO Michael Rapino at the helm, which grew into the most dominate company in music, with $15 billion in revenue reported in 2019.

After the sale, Sillerman went on another buying spree, purchasing the rights to Graceland, the Elvis Presley Estate, Simon Fuller‘s 19 Entertainment and an 80% stake in Muhammad Ali Enterprises. In 2011, he sold that company for $512 million and tried his hand at commercial real estate with decidely less luck, defaulting on a loan from Credit Suisse equalling $21.4 million.

“I’m not very knowledgeable about real estate,” he reportedly told the New York Post at the time.

In September 2012, Sillerman announced his biggest project to date on the cover of Billboard, sporting a black leather jacket, a global-shaped disco ball and a handkerchief in his pocket that famously read “F— Off.” 

“It’s a universal statement,” Sillerman told Billboard writer Kerri Mason. “I don’t know whether it’s directed at a specific individual, or a type of individual, or more as my interpretation of Albert Einstein‘s fabulous quote: ‘No problem can ever be solved from the same level of consciousness that created it.’ And that’s what I’ve done my whole life. So what he said so eloquently, I say, ‘F— off.'”

Profanity was part of a larger schtick punctuated with sexist, racist and generally inappropriate language that was softened by Sillerman’s own self-deprecating jokes with his Jewish heritage being the punchline.

“Some people loved Bob and some people hated him, there was no middle ground,” said James “Disco Donnie” Estopinal, a New Orleans dance promoter now living in Puerto Rico who served as Sillerman’s deal maker and helped bring in the dance promoters that would come to form the new SFX Entertainment.

With Finkel by his side and Estopinal giving the pair needed credibility, Sillerman set out to once again consolidate the dance music business by buying up dance promoters in Europe, Asia and North America. The orginal goal was to buy Pasquale Rotella‘s Insomniac, explained Estopinal. “That didn’t work out, but when we started talking, Insomniac’s acquistion price was $10 million,” he said. “When he did sell to Live Nation, the number was closer to $100 million — the only thing that changed was we’re out there buying promoters.”

Dance music was rapidly growing in popularity with ticket sales increasing by nearly 30% from 2011 to 2012, but most “electronic promoters were putting everything they owned into the next show,” explains Estopinal. “There was no retirement plan. Before Bob, the whole scene was a giant Ponzi scheme.”

Sillerman told Estopinal he had $1 billion to spend on the rollup — on an S-1 form announcing the IPO of SFX, Sillerman listed holdings that included online marketplace Beatport, the American-arm of Dutch company ID&T that produced festivals Tomorrowland and Sensation, Electric Zoo founders Made Events, German promoter i-Motion and Australia’s Stereosonic festival producer Totem Onelove Group.

“Some of those companies listed weren’t done deals,” Estopinal tells Billboard, adding that Sillerman misrepresented his financing and capitalization as he put SFX together. An October IPO on the NASDAQ raised $260 million for the company with shares priced at $13, but in the space of two-and-a-half years, the price of the company dropped to a penny a share. In February 2016, SFX filed for bankruptcy, brought down in a cash crunch that Estopinal now partially blames on overpaying for the assets that came to make up SFX.

“It’s easy to say that in hindsight,” Sillerman told Billboard in a June 9, 2016 article. “We bought companies based on what we anticipated — that we could bring in ­incremental sources of revenue.”

But the company had no serious strategy, a former employee told Billboard at the time, and Sillerman’s frequent misrepresentations angered investors, including a plan to take the company private in May 2015 that collapsed when it became clear that Sillerman didn’t have the $700 million needed to finance the deal. 

“At that time it was very exciting, but the mergers didn’t work in the U.S. in the way we thought they would,” Finkel said. “It didn’t scale and this round was young promoters that weren’t as established as the promoters from the first round” of buyouts in the 1990s. 

“When things were going bad, he was looking for ways to try and make it work,” Finkel said. When asked if Bob was dishonest about the company’s health, Finkel told Billboard, “It was more complicated than that. And sad. Bob had his own way of doing things and it wasn’t good in the end.”

In September 2016, U.S. district court judge Colleen McMahon ruled there was evidence that Sillerman likely misrepresented the go-private plan to inflate the company’s price and allowed a lawsuit by investors with the Guevoura Fund to move forward.

Sillerman’s actions signaled to the market that he “saw significant value in SFX. And because Sillerman was known as a savvy business mogul within the entertainment industry, his faith in the Company was interpreted as evidence that SFX was in fact valuable, even if that value was not yet reflected in the Company’s financial reports,” McMahon wrote.

In her ruling, McMahon said the buyout offer was likely made to distract attention from the company’s poor quarterly financial reports, which showed that SFX was bleeding money and attendance at its events dropping. She also criticized the investors and analysts watching the company, saying they “spent much of 2015 ignoring all indications that the Company was in a poor financial state” and ignored key developments like a decision by Moody’s to downgrade SFX’s credit rating — a development that “under normal circumstances would be a significant red flag” for investors.

Sillerman was eventually pushed out of the company by creditors and it re-emerged as LiveStyle in 2017 with entertainment veteran Randy Phillips at the helm. A year later, Sillerman was pushed into bankruptcy over an unpaid $7.4 million promissory note to React Presents during the SFX rollup. 

Lawsuits increasingly became a common part of his life, including a suit from a luxury real estate firm for breach of contract after he allegedly cut the firm out of a $114 million real estate deal without paying their commissions. In December 2016, former SFX board member Mitch Slater sued Sillerman for an unpaid $2.5 million loan from 2015. 

He was also starting to run afoul of the SEC — an audit by the firm BDO of his company Function(x) found that Sillerman allegedly broke the law when he transferred $6.1 million into his own personal account and withdrew $500,000 in cash “with no explanation” and “no supporting documentation.” Sillerman settled the case with the SEC in June, agreeing to a $179,000 fine and a ban from holding an officer or director role at any public company.

“He was a good guy, but he knew he did bad things,” Estopinal tells Billboard, noting that Sillerman was suffering from the complications of throat surgery through all of the SFX misadventure. Unable to eat solid foods, he was prone to horrible coughing fits and had to eat through a feeding tube.

“There were people who told me, ‘I’m not doing a deal with this guy, he’s going to die,’” Estopinal says. “He was never really at 100%.”

Estopinal says he last saw Sillerman at a deposition, but he remembers sending Sillerman a note after the bankruptcy, acknowledging the failures of SFX while also thanking him for the opportunity to be part of the company.

His response?

“He replied with an email that said, ‘Can I borrow a dollar?’” Estopinal said. “That seemed to sum everything up.”