Man alleges DraftKings helped famed bettor try and extort him

Masked man on cell phone
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In a court filing that reads like a Martin Scorsese movie, an unnamed plaintiff is alleging that famed bettor Gadoon “Spanky” Kyrollos attempted to extort him using information given to him by DraftKings Sportsbook.

John Doe said Kyrollos sent henchman to demand money

In the complaint, John Doe said he was accosted by a masked man on the street outside his Long Island City apartment and demanded $500,000 to be paid to Kyrollos and his associates. According to Doe, he had never met Kyrollos and they had spoken on the phone only twice nor did he owe him any money.

However, Doe has seemingly filed no legal action against Kyrollos and is instead suing DraftKings, claiming that the company leaked his personal information, including his address, to Kyrollos.

“DraftKings loaded the proverbial gun and put it in Spanky’s hand,” the complaint suggested.

When asked for comment, DraftKings provided SBC Americas the following statement:

“The complaint filed against DraftKings in March 2024 by an unnamed plaintiff is full of inaccuracies and baseless allegations. In the complaint, the plaintiff does not identify any DraftKings employee, but rather alleges on ‘information and belief’ that an unknown and unidentified DraftKings employee provided private account information to ‘Spanky’ and to additional unnamed third parties. DraftKings has found no evidence of anyone at DraftKings providing plaintiff’s information to a third-party, and DraftKings denies acknowledging any such ‘security breach’. Nor has DraftKings uncovered any improper activity by a DraftKings employee, or any activity on plaintiff’s account, relating to the allegedly unauthorized change of the email address associated with plaintiff’s DraftKings account. DraftKings is moving to dismiss the complaint by June 28.”

Kyrollos says his statement about having DraftKings info was a “bluff”

Late Tuesday night, Kyrollos took to Twitter to tell his side of the story and in doing so corroborated much of the info in a related lawsuit that indicates the John Doe in this case is the lawyer who filed the complaint, Steven Jacobs.

Kyrollos confirmed that he and his partners were using Jacobs’s DraftKings account to get down bets since DraftKings stopped accepting wagers from him several years ago. When it came time to withdraw and settle up, Jacobs allegedly claimed that DraftKings wouldn’t allow him to withdraw, but Kyrollos and his associate Oscar Jones believe Jacobs took the money and intends to keep it.

In his statement, Kyrollos claimed that Jacobs told him he owes people over a million dollars.

“The evidence seems to show that Steve Jacobs is either a sick compulsive gambler or a thief. My bet is on both. Either way he needs help,” he wrote.

As to why Jacobs might think Kyrollos received private information from DraftKings about his account? Kyrollos claimed this was a “bluff” to try to determine if Jacobs was telling the truth about his withdrawal issues.

“My strategy of following up on my suspicion was a test for Steve Jacobs. I told him — bluffing —  that I had the ability to receive information on the status of the payout from DK (I obviously do not have that power, nor am I connected with anyone who does have that power, given I am banned from betting at DK!). I wanted to gauge Steve’s response to my bluff; in particular, I was hopeful that if he was doing something wrong, that this bluff might encourage him to fess up.”

Complaint says DraftKings leaked personal info to Spanky

Doe says he went to his VIP host at DraftKings, Joe Di Chiaro, claiming that in February 2023 Kyrollos threatened him and said he knew people at DraftKings who would give him Doe’s information if Doe did not give him the money. He also allegedly warned Doe he knew dangerous people.

Doe’s claim referenced a 2012 case where Kyrollos and 24 others were indicted as part of a widespread illegal gambling ring. Kyrollos ultimately pleaded guilty to a felony charge.

At the time, Doe said he asked Di Chiaro to beef up security around his personal information and claims DiChiaro assured him measures would be taken to protect his account and that he would know if anyone tried to access it.

A month later, Doe said he was accosted on the street by a masked man. He immediately went to Di Chiaro, whom he alleged acknowledged there was some sort of breach on his account but that he couldn’t comment on a pending investigation.

The complaint did not include any of the alleged text communications between DiChiaro and Doe as exhibits.

Doe says DK account was hacked with inside help

In October 2023, Doe alleged that he woke up and could not access his DraftKings account. After some investigating, he learned that the primary account on the email was changed. He asserted that he did not okay the change, nor did he receive an email to his address about the change, which is standard operating procedure for switching emails on a DraftKings account.

Doe believes it was Kyrollos and his associates who facilitated the change and alleges that DraftKings was extremely uncooperative in providing details regarding the email switch. The complaint went so far as to suggest DraftKings helped facilitate the hack on Kyrollos’s behalf.

Doe is seeking at least $1 million in compensatory damages from DraftKings in addition to punitive damages. The case was initially filed in the Queens County Superior Court but has since been sent to the Eastern New York District Court.

DraftKings intends to file motion to dismiss

Right now, the judge is determining whether or not Doe can proceed under a pseudonym. DraftKings recently informed the court it had inadvertently become aware of Doe’s identity thanks to being served with papers that had his name on it. With that in mind, DraftKings is pushing for the identity of the plaintiff to be revealed.

In that May letter, DraftKings conveyed its intention to file a motion to dismiss the case.

DraftKings declined to comment to SBC Americas on this story. We have also reached out to Kyrollos for comment but have yet to receive a response.