Half-joking calls for Oprah Winfrey to run for President have been a thing for years, and they only got louder and more serious after Donald Trump ascended to the country's highest seat. With the next presidential election just two years away, Trump already has plans for 2020 and says he could beat the media mogul in a presidential race because he knows her "weakness," according to The New York Daily News.

He addressed a crowd during a stop in Pennsylvania about what might be to come. "I would love Oprah to win," he said of Winfrey winning the Democratic nomination. "I would love to beat Oprah. I know her weakness." 

Just what that weakness might be is unclear, but Trump once called Winfrey "insecure" after she hosted a 60 Minutes roundtable discussion, in which he claims she asked "biased and slanted" questions.

He seems to be pretty certain he could pull off a win against his one-time friend. “Wouldn’t we love to run against Oprah?” he went on to say in Pennsylvania. “I would love it. I would love it. That would be a painful experience for her.”

Back in 2000, Donald Trump reportedly floated Winfrey as a running mate in one of his first attempts at the Oval Office, but now it seems he wants her to run just to prove a point. It's a matchup that is highly unlikely, as Winfrey has shared many times that she has no interest in running for political office, despite speculation that her speech at this year's Golden Globes was an early attempt in a larger plan to run a campaign.