President Trump's toughest challenger in 2020 is himself

President Trump’s reelection chances could hinge more on his personality than the booming U.S. economy.

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That from famed pollster Mark Penn, who tells “WSJ at Large” host Gerry Baker that in all his years in politics, he’s never come across anyone like this president.

“I look at his numbers – 62 percent approve the job he’s doing in the economy. Only 32 percent like him personally,” he pointed out. “It’s the biggest personal-to-performance gap that I’ve ever seen and that is what is weighing the president down.”

Penn, who worked with the campaigns of both Bill and Hillary Clinton, is now Managing Partner of the digital marketing investment firm Stagwell Group and CEO of the MDC Partners marketing firm. He believes for Trump to win, he needs to sell voters on his economic prowess and downplay the negativity about him personally.

“The American public recognizes it’s his economy not Obama’s but those personal ratings are the lowest I’ve seen with somebody with those economic ratings,” he said. “He’s got to close that gap if he wants to do what normally happens, which is the economy is the number one variable.”

Still, Penn advises that when it comes to Trump, it’s wise to be skeptical about some polling data.

“I don’t trust those polls that have his ratings in the 30’s because he got 46 percent and 90 percent of his previous supporters support him,” he said. “I don’t trust anything below 43 right now.  I do think he’s somewhere between that 43 and 47 percent.”

Penn notes president's popularity will rise when the public begins to concentrate more on who is running on the Democratic side.

“He’s had no opponents so essentially the president is running against himself at this point and he’s winning or losing depending upon how you look at it,” Penn said. “And the Democratic candidates will have the first debate and that will begin to create a focus on how they’re all doing.”

Former Vice President Joe Biden is the Democratic Party’s frontrunner, but Penn warns that as he learned with former Secretary of State Hillary Clinton in 2008, being at the head of the pack early can be a disadvantage.

“There’s 23 [candidates]. That means there are 22 that are going to be fighting to bring you down,” he said. “And that’s why Biden is avoiding some of these places where he’s just going to be attacked.”

Penn, who calls South Bend, Indiana Mayor Pete Buttigieg the surprise of the field so far, sees the possibility that neither Biden nor anyone else will have enough delegates to score a decisive victory in next year’s Democratic Party convention.

“I think [California Senator] Kamala Harris has a good opportunity,” he said. “I think [Vermont Senator Bernie] Sanders and [Massachusetts Senator Elizabeth] Warren have a good opportunity and I think Mayor Pete [Buttigieg]. I think they may well have a perfect convention where nobody gets a majority on the first ballot and deals are going to have to be made.”

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But in the end, Penn said the outcome of the 2020 presidential election will depend a lot on what the current occupant of the White House does from here.

“Look, I’ve run incumbent presidential campaigns before,” he explained. “He’s got to show that he’s got a record, that he’s got a whole plan for the next term so that he can make a difference.  And he has to deal with his personality issues to reassure suburban voters or he’s not going to get them back.”