Epstein lost $10K bet to Trump over Marla Maples and sent a truck of baby food as payment

Epstein revealed the bizarre pregnancy-related wager during a 2016 conversation with Deepak Chopra, just months before Trump’s first election win
PUBLISHED NOV 14, 2025
Epstein says he lost a $10K bet to Trump over ex-Marla Maples and sent a truck of baby food as payment, emails show (Getty Images)
Epstein says he lost a $10K bet to Trump over ex-Marla Maples and sent a truck of baby food as payment, emails show (Getty Images)

WASHINGTON, DC: Amid surfacing of new emails related to Jeffrey Epstein, documents show that Epstein claimed to have lost a bet of $10,000 to Donald Trump, after the latter’s then-spouse, Marla Maples, became pregnant.

According to the email, Epstein paid off his wager in an unusual way by sending a truckload of baby food to Trump. 

Epstein paid Trump bet with baby food

Portrait of American financier Jeffrey Epstein (left) and real estate developer Donald Trump as they pose together at the Mar-a-Lago estate, Palm Beach, Florida, 1997. (Photo by Davidoff Studios/Getty Images)
Portrait of American financier Jeffrey Epstein and real estate developer Donald Trump as they pose together at the Mar-a-Lago estate, Palm Beach, Florida, 1997 (Davidoff Studios/Getty Images)

This new email was among the thousands of Epstein-related documents published on Wednesday by the House Oversight Committee, many of which refer to Trump.

Epstein revealed the bizarre pregnancy-related wager during a 2016 conversation with author Deepak Chopra, which took place just months before Trump’s first election win. Chopra emailed Epstein on July 29 that year seeking to arrange a FaceTime or Skype call with him.

“Btw,” Chopra said. “Do you know Marla Maples?” “Yes,” Epstein replied three minutes later.

“In fact when she told donald she was pregnant...lost a 10k dollar bet with him, and sent him a truck of baby food in in payment,” he added.

He said that he had not spoken to Maples for years since then. 

Trump's time with Marla Maples

NEW YORK - DECEMBER 20: Donald Trump and Marla Maples marry at the Plaza Hotel December 20, 1993 in New York City. (Photo by Sonia Moskowitz/Getty Images)Donald Trump and Marla Maples marry at the Plaza Hotel December 20, 1993 in New York City (Sonia Moskowitz/Getty Images)

Maples, a Georgia-born actress and singer, gave birth to Trump’s daughter Tiffany in October 1993, shortly after the then real estate tycoon divorced his first wife, Ivana Trump.

A few months later, the pair tied the knot at New York City’s Plaza Hotel. Among the many guests in attendance was Epstein, as archival video footage published by CNN in July revealed. Maples and Trump divorced in 1999.

New emails spark clash over Trump-Epstein link

In this handout, the mug shot of Jeffrey Epstein, 2019. (Photo by Kypros/Getty Images)
In this handout, the mug shot of Jeffrey Epstein, 2019 (Kypros/Getty Images)

Democrats on the House Oversight Committee released a collection of damning emails on Wednesday, November 12, many sent directly from Epstein. One of them referred to Trump as the “dog that hasn’t barked,” and in another, Epstein apparently alleged that Trump spent hours with one of Epstein’s victims.

In turn, Republicans on the House Oversight Committee on the same day released more than 20,000 pages of records from Jeffrey Epstein’s estate, declaring, “You deserve the full truth.” 

They released the records just hours after Democrats unveiled emails in which Epstein reportedly mentioned President Trump. 

The sudden release followed accusations from the White House and GOP lawmakers that Democrats had selectively leaked material to slander the president.

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