Spanky Not Surprised a 'Masked Man' Would Attack 'Unhinged Poker Player' He Says Owes Millions

It's one of the more convoluted stories we've seen in some time and it keeps getting more interesting by the hour.  Professional sports bettor and organizer for the popular sports gambling networking event BetBash,  Gadoon “Spanky” Kyrollos, late Tuesday outed a man he accuses of stealing large sums of money from him and "owes millions" to others.

The lawsuit claims that on 30 March 2023 in Long Island City, New York City, a masked man grabbed and violently spun him around, then threatened to kill the plaintiff unless he paid $500,000 to Spanky.

The filing alleged that unidentified staff in the “upper echelons” of DraftKings knowingly provided the plaintiff’s address, sensitive personal information, financial history, and betting history to Spanky.  DraftKings has denied the allegations and says it plans to file a Motion to Dismiss.

Spanky offered his side late Tuesday while identifying "John Doe" as New York attorney Steve Jacobs.

"Plaintiff / plaintiff's attorney Steve Jacobs is also a Senior Attorney who works at Herbert Smith Freehills Law Firm in New York City," Spanky claimed.

After offering some background on the matter, Spanky concluded: "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.

"I wound up talking to Steve Jacobs and he admitted to me that he owes over a million dollars ($1,000,000.00) to other people. He has a reputation in the poker community of being unhinged."

Spanky also noted that Jacobs had quite the reputation in the poker world.

Here is Spanky's statement in its entirety:

Let’s address Mr. ‘John Doe’ aka Steve Jacobs (Yes, you read that right, the plaintiff and the plaintiff’s attorney are the same person!)

Plaintiff / plaintiff's attorney Steve Jacobs is also a Senior Attorney who works at Herbert Smith Freehills Law Firm in New York City.

As background, my buddy Oscar Jones met Steve through a personal connection and was under the impression that Steve was a "whale" that we believed we could flip to get down.

In layman's terms, a "whale" is a losing player that can bet big on all of our behalf because the sportsbook, seeing his history of losing bets, has given him increased betting limits, hoping he will lose even more.

We would send Oscar the plays, Oscar would send them to Steve Jacobs and Steve Jacobs would then punch them in his account. (For those unaware of the betting landscape, I rely on guys like Steve Jacobs to bet, given DraftKings (DK) doesn’t allow me to bet at their establishment because I win). Oscar even gave Steve $82,375 of his own money to get the partnership started.

After a few months, and with the benefit of our consultation (via Oscar), naturally Steve won a substantial amount of money.

Fast forward 2 months to when it's time to settle up the proceeds of our partnership. Slight problem – Steve claimed DK was holding up the payout. He claimed that DK was asking him to sign an “affidavit of eligibility”. Oscar and I each advised him to file a complaint with the New York Gaming Board. Initially he refused, but we were insistent that he take up the matter with the regulatory authorities, and eventually he agreed to do that.

On February 6, 2023 at 8:33p Steve filed a complaint with NY Gaming via email and BCC’d Oscar on that email to “prove” he’d filed it.

For more than a month after that, Steve told us both that he had not yet received a response to the complaint he filed with regulators, and that he was still waiting with "fingers crossed".

Oscar and I both started to get suspicious.

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. Steve maintained that DK was holding up his withdrawal request, and that he was waiting on a response to a complaint he filed with the New York Gaming Board.

Oscar then had a brilliant strategy for following up on our suspicion; he had the idea to use New York's Freedom of Information Law (FOIL) to request, from the regulators, copies of the complaint that Steve Jacobs said he had filed against DK. What comes next is crazy! What Steve Jacobs never admitted to us was literally 5 minutes after filing the complaint, he sent them a second email at 8:38 pm on February 6, 2023 saying that the complaint he "filed" in his first email was an "accident".  5 minutes!

In his "accident" letter, he apologized - saying he was a "gaming lawyer and drafted it for a gaming training module”. Both the complaint and cancellation can be seen attached below and can be freely obtained via FOIL.

I believe one of three things happened: Either 1) Steve Jacobs wound up stealing the money, or (2) he gambled it all away or (3) he just booked our bets himself (instead of placing the bets at DK) - hoping we would lose.

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.

I wound up talking to Steve Jacobs and he admitted to me that he owes over a million dollars ($1,000,000.00) to other people. He has a reputation in the poker community of being unhinged

Although he never told me what happened with our winnings, which were supposedly being withheld after he tried to withdraw them in January of 2023, he did manage to, in March of 2023, settle another lawsuit against him, by paying plaintiff Jonathan Bronson $270,814. Steve Jacobs is involved in several lawsuits for hundreds of thousands of dollars, on both sides (but especially on the Defendant side), as John Doe in many of them. You've all heard of robbing Peter to pay Paul; this guy robbed Spanky to pay Johnny.

What a mess.

Steve Jacobs is now seeking compensation by way of a frivolous lawsuit against DraftKings - to either pay off other debts or to keep gambling. He claims this incident happened in March 2023 but yet he waited till June 2024 to file a suit? 15 months! Did he run out of money to feed his gambling habit?

I never threatened Steve nor sent a “masked man” to threaten him; however, given that Steve Jacobs owes over a million dollars ($1,000,000.00) to so many people, his claims don’t surprise me.

I never received any information from anyone at DraftKings about Steve Jacobs. FOIL was all we needed to prove this guy to be a shyster.

Sorry Steve Jacobs, but “John Doe” ain’t gonna cut it this time. You wanna try and steal money from people to feed your gambling habit and then play the victim? You want to smear my name and Oscar’s name and DraftKings' name? All while remaining anonymous!?! You use your lawyer badge to tie up the court’s valuable time instead of seeking the help you desperately need. Steve Jacobs is a complete loser!

To @HSFlegal
, you have a bad apple in your midst. Can you expect him to represent your clients while his mind is preoccupied with whether the Yankees will win by at least 2 runs or how he will find funds to feed his gambling habit?His behavior seems to be that of a professional con artist.

To my fellow bettors out there: there is a lesson to be learned here; be careful of who you deal with. Do your due diligence. Be wary of being too trusting based on appearances, because this case teaches us that even people who appear like they should be highly credible and highly trustworthy (e.g. Steve Jacobs, a high powered officer of the court /New York attorney for Herbert Smith Freehills) can turn out to be a con-man, a liar, and a thief.

Like I’ve always said, as a professional sports bettor, winning is just the beginning. Scum like this are everywhere you look. You do your best to try and avoid them but they always seep through.

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Gambling911.com cannot independently verify whether Steve Jabobs is the individual who filed the suit and/or filed on behalf of another individual. 

Jacobs is listed on the Herbert Smith Freehills website as a Senior Associate at the firm.

According to job recruitment firm Indeed, a senior legal associate is a more advanced associate solicitor who typically possesses five or more years of experience. Sometimes also called managing associates, senior associates often take on more leadership responsibilities in addition to their legal duties as fully qualified and practicing lawyers.

He has extensive experience in handling complex internal investigations and regulatory investigations, including FCPA, AML, and OFAC investigations, as well as those that concern data privacy.

Steven hosts a podcast series called The Bettor’s Verdict, on which he is joined by industry insider guests to discuss current issues in gambling law, sports law, and digital law.

Jacobs graduated Cum Laude from Fordham University School of Law where he was a Wilkinson’s Scholar.

Herbert Smith Freehills is recognised as one of the world's leading international law firms, by clients, by peers and our communities.