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In a 1999 monologue on “The Tonight Show,” then-host Jay Leno joked about Donald Trump’s presidential aspirations.

At the time, Trump was best known as a businessman and realtor who often found himself in the gossip pages. “The Apprentice” had yet to hit airwaves, and he had not married his current wife, Melania.

Fast-forward 18 years, and Trump is set to become the 45th President of the United States.

“And Donald Trump announced he is forming a presidential exploratory committee. Donald Trump wants to run for president,” Leno told his audience. “Did you see him on Larry King? He said he wants to give the country a change from Clinton.”


“A change?” Leno wondered aloud. “Trump’s a womanizer, he’s got marriage problems, he’s involved in all kinds of strange real estate deals….he is Clinton!”

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Leno then went through the list of possible presidential candidates and didn’t seem too impressed.

“Our choices for president are…Donald the Trump, Bush the Chump, Gore the Lump, or Buchanan the Rump” Leno joked. “Or, stick with what we’ve got — Clinton the Hump!

Years later, Leno would talk about his experience with Trump at at White House Correspondents Dinner. According to Leno, Trump did not stand and clap when President Barack Obama was introduced to the crowd.

“What are we, in school? What is this, the eighth grade?” Leno said. “You respect the office of the presidency.”

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