'Best boss ever': Karoline Leavitt reveals the side of Trump few see behind closed doors

Karoline Leavitt said she has seen Trump have personal moments with common people that have stayed with her during her time in the White House
President Donald Trump, accompanied by White House Press Secretary Karoline Leavitt,  walks towards the media as he departs on Marine One on the South Lawn of the White House on February 27, 2026, in Washington, DC (Getty Images)
President Donald Trump, accompanied by White House Press Secretary Karoline Leavitt, walks towards the media as he departs on Marine One on the South Lawn of the White House on February 27, 2026, in Washington, DC (Getty Images)

WASHINGTON, DC: Karoline Leavitt is in her final days as White House press secretary, and during her last round of interviews on Thursday, August 27, she had plenty to say about the president she has worked for over the past 20 months.

Leavitt called President Donald Trump the “best boss” she has ever had and recalled seeing a more personal side of him while traveling with him and meeting Americans away from the cameras.



Karoline Leavitt reflects on 20 months working for Trump

Speaking with NewsNation, Leavitt said one of the biggest things she has learned from Trump is how to deal with the media.

She pointed to his years as a businessman in New York, saying he had been dealing with reporters and appearing in the tabloids long before she was born.

“He’s a pro at this game, and he gets how it’s played,” she said.

Leavitt said she has learned by watching Trump handle the press and by getting an understanding of how he thinks.

JOINT BASE ANDREWS, MARYLAND - AUGUST 21: U.S. President Donald Trump shows copies of recent headlines as he speaks with reporters with Press Secretary Karoline Leavitt looking on before boarding Air Force One on August 21, 2026 in Joint Base Andrews, Maryland. President Trump is traveling to South Carolina for a campaign rally with Darline Graham. (Photo by Win McNamee/Getty Images)
President Donald Trump shows copies of recent headlines as he speaks with reporters with Press Secretary Karoline Leavitt looking on before boarding Air Force One on August 21, 2026, in Joint Base Andrews, Maryland (Win McNamee/Getty Images)

She also said Trump sometimes jokes that he is the White House's real communications director.

Then she turned to what she has seen of him personally during her time in the administration. “He is the best boss I have ever had,” Leavitt said.

She described Trump as funny and said he has a strong sense of humor.

“He has a huge heart. He’s hospitable, he’s generous, and he loves this country and the American people,” she said.



Leavitt also said she has seen Trump have personal moments with Americans that have stayed with her during her time in the White House.

Karoline Leavitt on 'bittersweet' White House exit

Leavitt then addressed her departure during a separate appearance on 'Fox & Friends' on Thursday.

She described leaving the press secretary's job as “a little bit bittersweet.”

The bitter part, she said, is walking away from a position she loves and from working directly for Trump.

“It’s been the honor and blessing of a lifetime to work for this president,” Leavitt said. “There will never be another like him.”

WASHINGTON, DC - APRIL 10: White House press secretary Karoline Leavitt carries her son Niko Riccio, as she walks along the Collonade before U.S. President Donald Trump departs from the White House on April 10, 2026 in Washington, DC. President Trump is traveling to Charlottesville, Virginia. (Photo by Andrew Harnik/Getty Images)
White House Press Secretary Karoline Leavitt carries her son Niko Riccio as she walks along the Collonade before President Donald Trump departs from the White House on April 10, 2026, in Washington, DC (Andrew Harnik/Getty Images)

Leavitt has served as Trump's press secretary for about 20 months. She is leaving the position to spend more time with her young family, including her newborn daughter.

She said her children are at an important stage in their lives and need their mother at home more. But she is not walking away from the administration altogether.

Leavitt said she plans to continue working with Trump as a top outside adviser after leaving the White House.

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