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Nov 14, 2020
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About this Deal

A group of recent Ivy League graduates is making a run on lotteries across America.

So far they’ve won more than $6 million from lotteries in Indiana, Missouri, Washington and the District of Columbia.

Exactly how they’re doing it — and how much they are profiting, if any — remains a mystery.

The unusual winning streak first came to light in Indiana after the apparent leader of the group, a 27-year-old Princeton University graduate named Manuel Montori IV, cashed in 61 winning Hoosier Lottery scratch-off tickets on a single day in September.

All of the winnings came from the same game, $7,000,000 MEGA CA$H, which sells for $30 a ticket. Most of Montori’s winners were for $1,000, but three were for $10,000, bringing his total haul to $88,000.

But that was just one day. Just one state.

Manuel Montori hold a ceremonial check for the $100,000 prize he claimed from the DC Lottery in March 2019. Montori and two of his former classmates from Princeton University have won several other big lottery prizes in Indiana, the District of Columbia and Missouri.
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Montori has been on an 18-month winning streak, or so it would appear. It includes much larger paydays and is part of a scheme that includes at least three other Princeton alumni: Matthew Gibbons, Hannah Davinroy and Zoë Buonaiuto. All of them are associated with an obscure company Montori founded last year called Black Swan Capital LLC.

Their biggest payday came a week after the Hoosier Lottery bonanza. Montori collected a $5 million top prize from a scratch-off ticket in Missouri on Oct. 6. Other winnings identified by IndyStar include:

$121,000 Davinroy collected from the Missouri Lottery in September.
$1 million Davinroy collected on behalf of Black Swan from the D.C. Lottery on Dec. 16, 2019.
$100,000 Montori collected from the D.C. Lottery on March 25, 2019.

They also had a 1-in-5 shot at another $1 million in a Hoosier Lottery second chance drawing at the Indiana State Fair last year. Gibbons was one of the finalists selected from players who submitted non-winning tickets. He didn't win that one, but did collect a $500 consolation prize.

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It’s a good bet, however, they’ve had other big paydays that haven’t come to light yet.

Their record raises several questions. Are Montori, Gibbons, Buonaiuto and Davinroy really that lucky? Have they found a way to beat the lottery at its own game? Or are they investing far more money than they are winning in a scheme doomed to fail?

'They would clean us out'
In Indiana, the group appears to have gone on a frenzied buying spree in the final months of the MEGA CA$H game.

“Basically, they would clean us out,” said Darian Crites, a manager at Smoke ‘n’ Lotto in Bloomington, which sold one of the winning $10,000 tickets Montori claimed in September.

She said two women who identified themselves as Hannah and Zoe were involved in purchasing as many as 400 tickets at time during several visits that began in May. They said they were working for a man conducting a study and the results would later be shared on YouTube.

After emptying the store’s inventory on their initial visit, Crites said one of the women asked to be notified when a new supply of tickets arrived. The woman would then return to buy up the new tickets. The pattern continued until the lottery informed the store that the game was sold out.

Ultimately, they purchased about 1,600 tickets at a cost of $48,000, Crites estimated.

And that was just at her store.

The other 60 winning tickets Montori cashed in were purchased from more than four dozen different gas stations, liquor stores and other lottery outlets all over Indiana, the Hoosier Lottery website shows. If they purchased similar amounts at each store, Montori and his group would have spent at least $2.3 million. And that doesn’t account for the time, travel or people needed to scoop up tickets from places as far flung as Mishawaka, Corydon, Indianapolis, Richmond and Terre Haute.

A winning $7 million ticket might have made Montori and his friends rich. But without the top prize, the group’s expenses may very well have exceeded its winnings in Indiana. Without knowing the size of the initial outlay, it’s impossible to know.

In other states, however, the group appears to have struck pay dirt.

This summer in Missouri, two women snatched up thousands of $5,000,000 Cash Extravaganza tickets during a series of visits to Break Time, a convenience store and gas station near a busy I-70 interchange in Columbia.

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