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Why Andrew Gillum is incurring so much of Trump’s ire

President Trump regularly attacks his Democratic foes, and one who is increasingly drawing his attention is Tallahassee Mayor Andrew Gillum, who hopes to be the next governor of Florida.

Trump, who campaigned on the promise of being a voice for the forgotten people against the elites, tweeted that the Ivy League education of Ron DeSantis, the Republican candidate for Florida governor, was among the factors that make him a better choice than Gillum, who attended one of Florida’s historically black universities.

The part of the tweet that made the most news was Trump calling Gillum a thief. Some thought Trump’s attack was racist, given his history of associating black men with criminal activity. But Gillum stopped short of lobbing the accusation himself.

“I have not called the president a racist, but there are racists in his sympathizers who believe he may be, which is why they go to his aid, which is why he has provided them cover. I believe his cover has led to much of the degradation in our political discourse,” Gillum said Thursday on CNN.

While campaigning in Florida on Wednesday, Trump continued the jabs, calling Gillum “a failed mayor,” blaming him for Tallahassee’s crime rate and attempting to pit Gillum against police:

Andrew Gillum wants to throw open your borders to drug dealers, human traffickers, gang members and criminal aliens. And Gillum supports deadly sanctuary cities. He wants to abolish ICE and he signed an extreme, left-wing pledge that supported an end to all borders....
Andrew Gillum is too extreme for the people of Florida.... And he’s also weak on crime. 
On Andrew Gillum’s watch, there were more murders last year ... than any year in the history of Tallahassee. And Gillum is weak on corruption. Tallahassee is among the most corrupt cities anywhere in the United States. Is this really what you want in the state of Florida?

The line of attack associating Gillum with illegal immigration seems meant to instill fear in Trump’s base but also to sway the independent Florida voters that swung to Trump. Enthusiasm for Gillum is high among Democrats headed into the midterm elections, which require Trump to rely on his most effective motivator: fearmongering.

Another high-profile Democrat, Rep. Beto O’Rourke (Tex.), has launched a Senate campaign in a southern red state that aims to be inclusive and has garnered national attention. But unlike O’Rourke, Gillum consistently leads his opponent in the polls.

Gillum is one of the Democrats running who is viewed as a successor to former president Barack Obama’s legacy, and Obama’s visit Friday to Miami to campaign for Gillum seems to confirm that. A Gillum win would be a coup for Democrats in a state that went for Trump

So while the president is leaning heavily on fear to rally votes, it could be that it partly stems from what he is dealing with himself. Trump seeks to put “yes men” in positions of influence across the country. And DeSantis has signaled that he could be that. The president noticed him during the GOP gubernatorial primary when the former congressman appeared on Fox News frequently to defend the president. While Trump did not know much about him, DeSantis’s support for Trumpism, which he communicated clearly in one of the most pro-Trump ads of the midterms, was more than enough for him to win the president’s praise.

It is clear, perhaps obvious, to Trump that Gillum could do great harm to Trump’s agenda in Florida, an important stronghold in the South. If, in the midterms, the president loses those Florida independents who voted for him, he might not get them back in 2020. And if this goes beyond Florida, Gillum could be a leader in the region’s rejection of Trumpism in favor of a worldview that includes many of the people Trump appears to want to exclude.