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Obama’s New Gig: Gleefully Needling Trump

Former President Barack Obama bounded off the stage in Philadelphia last week after his debut as Joseph R. Biden Jr.’s 2020 battering ram and pronounced himself pumped — and even a bit delighted at the chance to troll his troll, President Trump.

“Oh man, that felt good,” Mr. Obama told a friend in a phone call — and he let Mr. Biden’s staff know that the ungainly format of the event, a “drive-in rally” where he addressed hundreds of supporters in cars in a stadium’s parking lot, had worked surprisingly well, according to several people close to the former president who spoke on the condition of anonymity to discuss private conversations.

In 2016, Mr. Obama took his whacks at Mr. Trump on behalf of Hillary Clinton. Then he stepped up his criticism of his successor during the 2018 midterm elections. This summer, during the virtual Democratic convention, he offered a damning jeremiad against the president, warning that Mr. Trump’s re-election would “tear our democracy down.”

But nothing Mr. Obama has said during the Trump era compares with his gleeful slag-heaping of scorn upon Mr. Trump in the closing days of the 2020 campaign, part of a two-week burst of activity that will culminate in a joint rally with Mr. Biden being planned for this coming weekend, according to Democratic officials.

“What’s his closing argument? That people are too focused on Covid?” Mr. Obama said on Tuesday at an Orlando rally intended to energize voters in Florida, a perennial neck-and-neck battleground and Mr. Trump’s adopted home state. “He said this at one of his rallies. ‘Covid, Covid, Covid,’ he’s complained. He’s jealous of Covid’s media coverage.”

Mr. Trump was apparently watching. And he complained about how much media coverage Mr. Obama was getting. “@FoxNews is playing Obama’s no crowd, fake speech for Biden, a man he could barely endorse,” Mr. Trump tweeted at the 21-minute mark of his predecessor’s speech.

Mr. Obama’s return to the trail is driven by a desire to help Mr. Biden in any way he can, according to friends and Democratic aides. He has already lent his name to about 50 fund-raising emails on behalf of Mr. Biden and other Democrats, in addition to cutting get-out-the-vote ads appearing in 15 swing states and raising millions of dollars through online fund-raisers.

Above all, he has been eager to reverse roles with his loyal helpmate, these allies and associates say, and willing to throw punches that would undermine the former vice president’s image as a national healer if Mr. Biden took the swing himself.

It has also allowed Mr. Obama to have fun at a time when many Biden supporters have been anxiously following state polling averages in fear of a second Trump surprise. Mr. Obama is clearly relishing the chance to strike back at Mr. Trump, who has not only baited him for years but has also tried to eradicate his legacy, policy by policy.

“He’s plainly having a good time out there — like a guy with a lot of material to work with who’s been waiting a long time to share it,” said David Axelrod, a longtime campaign and White House adviser to the former president.

Credit…Kriston Jae Bethel for The New York Times

Mr. Obama kicked off the Philadelphia rally by giddily referring to a recent New York Times report that detailed previously unknown financial holdings of the president’s in China and other foreign countries.

“Can you imagine if I had a secret Chinese bank account when I was running for re-election?” Mr. Obama asked after ridiculing lower-than-expected recent TV ratings for the president and mocking him for contracting the coronavirus after flouting safety measures. “They would’ve called me Beijing Barry.”

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At his second rally, on Saturday in a Miami parking lot, Mr. Obama went after Mr. Trump with an ear-to-ear smile that at times gave way to raw-nerve rage.

Popping up in Florida just as Mr. Trump arrived in West Palm Beach to cast his vote, the former president slammed his successor for mishandling the coronavirus pandemic, “fumbling” the economy, asking aides about selling Puerto Rico, musing about killing the virus by injecting disinfectant and once reportedly floating the idea of blasting hurricanes with nuclear weapons.

Mr. Obama concluded by comparing Mr. Trump, unfavorably, to the state’s signature meme, a feckless and addled Everyman known for bizarre and idiotic behavior.

“Florida Man wouldn’t even do this stuff!” Mr. Obama said. “Why do we accept it from the president of the United States?”

Mr. Trump took instant notice. “Nobody is showing up for Obama’s hate laced speeches,” the president wrote on Twitter moments after Mr. Obama had finished. “47 people! No energy, but still better than Joe!”

There were, in fact, dozens of cars at the event, and the Biden campaign said hundreds of potential attendees had been turned away to comply with social-distancing requirements.

Mr. Obama’s manicured vitriol falls considerably short of anything Mr. Trump might say in the course of a typical rally, and so far the post-speech fact-checks have been a comparatively light lift. An Obama staff member said that all of his preplanned zingers had been fact-checked.

But his tone, nonetheless, represents a sharp divergence from the 2016 summons by his wife, Michelle Obama, in support of Mrs. Clinton: “When they go low, we go high.”

Credit…Todd Heisler/The New York Times

Mrs. Obama, who has recorded videos for the Biden campaign, has no plans to appear at events in person this campaign, Democratic aides with knowledge of her plans said. Her husband, for his part, is intent on expending his political capital now, even if it involves abandoning his characteristic reluctance to sling insults at Mr. Trump, a man he has privately described as beneath contempt.

In conversations with Mr. Biden’s team, the former president and his aides mapped out a broad endgame strategy, consisting of online events and in-person appearances in critical battleground states targeting Black voters and young people, the groups he believes are most receptive to his message. The details of his schedule have remained in flux, dependent on the severity of the pandemic and the shifting needs of the campaign.

In those conversations, Mr. Obama outlined the role of “happy warrior,” of attacking Mr. Trump directly in a way he had never done before, but with the lacerating humor he employed during his two campaigns for president.

Some of his slaps are spontaneous, but many have been carefully workshopped — including the “Beijing Barry” line, which was delivered the day before the final presidential debate and was deployed to defuse Mr. Trump’s attacks on business deals in China pursued by Mr. Biden’s son Hunter, aides said.

Mr. Obama’s bellicose approach had another benefit that was not immediately evident until he began working on his remarks this month, according to Democratic aides.

The former president, adjusting to the political needs of the campaign, has gradually taken on the classic bodyguard role embraced by Mike Pence and previous Democratic vice-presidential candidates, enabling Mr. Biden’s running mate, Senator Kamala Harris, to avoid having to make those attacks herself and remain largely above the fray.

Yet for all of his continued popularity with Democratic voters, Mr. Obama is not on the ticket in 2020 — and his frenetic late campaigning on behalf of Mrs. Clinton did not prove decisive four years ago.

And his presence, especially in a complex state like Florida, is not universally positive.

”Obama’s Cuba policies were deeply unpopular with many voters in Southern Florida, and for all of his post-presidency popularity, he also carries some real liabilities,” said Alex Conant, a veteran political consultant who worked for Senator Marco Rubio, a Cuban-American Republican who opposed Mr. Obama’s attempt to normalize relations with the government in Havana.

“Obama’s always been skillful at driving a message and twisting a knife,” Mr. Conant added. “But his political capital wasn’t transferable when he was president, and it’s unclear if it is now.”

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