Group of Ivy League grads are buying massive amounts of lottery tickets and winning

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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.

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 DC Lottery on Dec. 16, 2019.

$100,000 Montori collected from the DC Lottery on March 25, 2019.

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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.

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Montori and his Ivy League chums aren’t talking about their lottery gambit. All four have avoided interviews and generally kept a low profile regarding their winnings across the country.

Montori appears to have posed for just one of the ubiquitous jackpot winner photographs. In a promotional shot for the DC Lottery, he has a big grin as he holds an even bigger check. He is wearing a black t-shirt and dark-rimmed glasses with a faint beard and hair down near his shoulders.

Public records and social media sites indicate Montori has lived in Florida and New Jersey and is the son of a prominent Peruvian businessman who lives in Florida. He has no obvious connection to Indiana or other locations where he’s won big lottery prizes.

He attended the Phillips Exeter Academy in New Hampshire, one of America’s most elite boarding schools and alma mater of President Franklin Pierce, 19 U.S. senators and Facebook founder Mark Zuckerberg. He was co-president of the Republican Club and on a four-member team that won the Yale University Economics Association's annual High School Economics Competition during his senior year.

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