‘Letters to Trump’ promises 150 letters from Oprah Winfrey, Kim Jong Un and more

North Korean President Kim Jong Un stands formally in front of flags next to then-U.S. President Donald Trump
The leaders of North Korea and the U.S. met in Singapore in 2018. Kim Jong Un’s “beautiful letter” to former President Trump will be in the latter’s new book, “Letters to Trump.”
(Evan Vucci / Associated Press)

President Donald Trump, formerly of the White House and now of Florida, is getting ready to release a new book of letters he has received from “some of the biggest names in history throughout the past 40 years,” his publisher said Thursday.

“From President Richard Nixon, to Princess Diana, and from Hillary Clinton, to Chairman Kim Jong Un, no book offers a glimpse into history quite like ‘Letters to Trump,’” reads a note on the website of Winning Press Publishing, an imprint co-founded by Donald Trump Jr. The publisher promises 150 pieces of private correspondence to the former host of “The Apprentice” and “Celebrity Apprentice” from all sorts of famous folks.

President Reagan, Oprah Winfrey, Sen. Ted Kennedy, Gov. Mario Cuomo, Arnold Palmer, Jay Leno, Liza Minnelli and Regis Philbin are among the correspondents, according to Axios, with Philbin addressing Trump as “My Dear Trumpster.” The letters were hand-picked by Trump for inclusion and come with commentary from the ex-president.


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Winfrey’s letter, written years ago, was in response to a missive from Trump and a complimentary excerpt he’d sent her from his 2000 book, “The America We Deserve.”

“At that time I announced that my first choice for vice president would be Oprah Winfrey. Again the political elites chortled — Oprah Winfrey! They just don’t understand how many Americans respect and admire Oprah for her intelligence and caring. She has provided inspiration for millions of women to improve their lives, go back to school, learn to read, and take responsibility for themselves. If I can’t get Oprah, I’d like someone like her,” Trump wrote in “The America We Deserve.”

“I have to tell you your comments made me a little weepy,” Winfrey responded, per Axios, also writing, “It’s one thing to try and live a life of integrity — still another to have people like yourself notice.”

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In Trump’s commentary, obtained exclusively by the bullet-point news outlet, he noted, “Sadly, once I announced for president [for the Republican nomination, in 2015], she never spoke to me again.”

Trump announced his book Thursday on Truth Social, writing, “Great news! My new book, ‘LETTERS TO TRUMP’ is available for pre-order today. The most incredible letters that I have received over many years.”

Winning Team, also co-founded by former Trump fundraiser Sergio Gor, published Trump’s photo book, “Our Journey Together.”


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Trump’s exchange of letters with Kim went public in 2019, when the North Korean leader “said with satisfaction,” via the country’s state-run news agency, that he had received a letter “of excellent content” from the U.S. commander in chief.

“Appreciating the political judging faculty and extraordinary courage of President Trump, Kim Jong Un said that he would seriously contemplate the interesting content,” the agency said without elaboration. The White House did not confirm at the time that there had been correspondence between the leaders.

The existence of the Kim letters came up again when Bob Woodward published his audio book “The Trump Tapes.”

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“Nobody else has them. But I want you to treat them with respect. ... And don’t say I gave them to you, OK?” Trump says in a Woodward recording as he hands over the letters to the reporter. “I think it’s OK. Normally, I wasn’t going to give them to [you].”

When Trump returned 15 boxes of materials to the government in early 2022 — papers he had taken with him when he left office in January 2021 — the contents reportedly included the original copy of a letter that former President Obama left for him when Trump was sworn in and letters written to Trump by the North Korean leader.

Trump’s retention of classified documents is one area of investigation being handled by DOJ-appointed special counsel Jack Smith.


“Letters to Trump” will set fans back $99 for a hardcover edition or $399 for the same edition with a bookplate signed by Trump. It comes out April 25.

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