Lottery Lawyer Accused of Bilking America’s Biggest Jackpot Winners Stands Trial

The trial kicked off this week of a so-called “,” accused by federal prosecutors of siphoning $107 million from three jackpot winners he was paid to advise.

Turns out “Lottery lawyer” Jason Kurland, above, was not the best person to offer financial advice to jackpot winners after all. That’s according to federal prosecutors. (Image: David Handschuh/NYLJ.)

Feds say Long Island attorney Jason “Jay” Kurland steered his clients’ money into his own merchant cash advance business. He also lost multiple millions in a Ponzi scheme. He plowed yet more money into a disastrous venture to sell personal protective equipment (PPE) to the state of California, according to prosecutors.

Until his arrest in August 2020, Kurland was America’s foremost counsel to the suddenly super-rich, advising lottery winners on how to protect themselves, their anonymity, and their money.

In 2018, he began representing the , the anonymous individual who that year purchased a $1.5 billion Mega Millions ticket at a South Carolina convenience store. This individual is one of the three victims, according to prosecutors.

Now, Kurland is facing conspiracy charges, wire fraud, and money laundering.

Ponzi Disaster

The court heard he initially offered sensible investment advice. But once he gained his clients’ trust, he began looking at more creative ways to grow their money. This included his brother-in-law’s plastic surgery business, offering “Brazilian butt-lifts” at $5,000 a pop.

It included Cheddar Capital, a company he part-owned with former securities broker Frank Smookler and Frankie Russo, the son of late Colombo crime family capo, Joseph “JoJo” Russo.

Powerball winner Nandlall Mangal testified that Kurland declared neither his interest in Cheddar Capital to clients nor his 1% finder’s fee.

If I had known that he was getting paid back then, yes it would have made a difference. And if he was getting paid, it wasn’t because of my best interests,” Mangal said.

In 2018, Smookler, Russo, and Kurland believed they had spied a unique business opportunity. A Long Island jewelry dealer named Greg Altieri told the trio in confidence he was buying pieces at “clearout” prices and flipping them for a 30% to 70% profit. What could possibly go wrong?

In 2020, Altieri was busted by the FBI for running a $200 million Ponzi scheme. According to federal prosecutors, some $80 million of that came from Kurland’s lottery clients.

Panic Investment

Kurland and his accomplices tried to cover their losses by panic-investing in the PPE business during the height of the pandemic. But this turned out to be another fraudulent enterprise operated by Christopher Chierchio, a reputed soldier in the Genovese crime family. The money was never seen again.

“Kurland convinced his largest lottery client to invest $19.5 million,” Assistant US Attorney Louis Pellegrino told the court. “But the people running the deal told Kurland they’d need to double that amount, so he simply took the winner’s cash without permission.

He took it right out of his lottery client’s bank account, which he controlled,” he added.

Smookler and Russo have already pleaded guilty to fraud and have agreed to testify against Kurland. Chierchio is also facing charges of wire fraud, wire fraud conspiracy, money laundering, and money laundering conspiracy.

Kurland’s lawyer, Tim Kasulis, argued his client was a victim, who he said was played for a “dupe” by the other three.

The case continues.