Democrats eyeing 2028 can't escape Trump's trolling

President Trump has yet to decide about his own legally iffy bid for a third presidential term, but he has many views on the Democrats who are looking to succeed him.

The master troller has been hard at work on the 2028 field, mocking some while boosting others.

Former Biden Transportation Secretary Pete Buttigieg was a recent victim. Mr. Trump blamed him for terrifying radar and radio outages at Newark Liberty International Airport in Newark, New Jersey.

“Pete Buttigieg, who was secretary of transportation, had no clue what the problem was,” Mr. Trump said. “He had no clue. Zero. Zero. But he wants to run for president. I don’t think he is going to do too well.”

During a press conference last week in the Oval Office, Mr. Trump added that Mr. Buttigieg “drives to work on his bicycle with his, in all fairness, with his husband on the back, which is a nice loving relationship.”

“But he didn’t have a clue,” he said.

Michigan Gov. Gretchen Whitmer faced the opposite problem — a political embrace from Mr. Trump, who met with her during a visit to her state to celebrate his first 100 days back in office. The hug set tongues a-wagging, with hardcore Democrats questioning whether Ms. Whitmer was doing enough to resist the man they see as a dictatorial menace to democracy.

She was taken aback when Mr. Trump gave her the stage to make brief remarks.

“I hadn’t planned to speak,” she said, before celebrating Mr. Trump’s announcement that new planes were coming to a local Air National Guard base. “I am really damn happy we are here. … I am so grateful this announcement was made today.”

Scott Jennings, a Republican strategist and political commentator who traveled with Mr. Trump to Michigan, reveled in the president’s behavior.

“My observation is that he should take great delight in trolling these people,” Mr. Jennings said. “They all deserve it and there’s nobody better at exposing how silly they are than President Trump.”

Mr. Trump has long been a fan of political punditry — at least when he’s offering it.

For the last decade, his chief targets were usually those running against him. He dubbed President Biden “Sleepy Joe” and ribbed then-Sen. Marco Rubio as “Liddle Marco” and Sen. Ted Cruz as “Lyin’ Ted” — complete with the apostrophe.

With the GOP now firmly under his thumb — Mr. Rubio is now his secretary of state and Mr. Cruz a top cheerleader for Mr. Trump in the Senate — the president is taking steps to shape the 2028 Democratic field.

He has dubbed sports personality Stephen A. Smith a cut above the rest.

“I have been pretty good at picking people and picking candidates, and I will tell you I would love to see him run,” Mr. Trump said over the phone at a NewsNation town hall.

“Steve A. — he is a good guy. He is a smart guy,” Mr. Trump said. “I love watching him.

“He has good entertainment skills, which is very important. People watch him. You know, a lot of these Democrats I watch, I say they have no chance.”

Mr. Trump’s nickname game remains strong.

He has referred to Mr. Buttigieg as Mad Magazine nerd “Alfred E. Neuman.” California Gov. Gavin Newsom is “Newscum” and New York Rep. Alexandria Ocasio-Cortez is “Evita.”

Mr. Trump also has telegraphed other likely attacks, including poking fun at Illinois Gov. J.B. Pritzker’s rotund figure.

“He’s too busy eating. He wants to eat all the time,” Mr. Trump said on the campaign trail last year. “‘I’ll have five burgers, please.’ Who the hell orders five burgers?”

That’s reminiscent of his previous swipes at former New Jersey Gov. Chris Christie, whose weight provided endless fun for Mr. Trump.

Of course, Mr. Christie also had the same problem Ms. Whitmer now faces. After the feds rushed assistance to New Jersey after Superstorm Sandy in 2012, Mr. Christie gave President Obama a cringe-inducing hug. He then spent years trying to justify or explain it away to GOP voters.

Jonathan Capehart, a liberal political analyst, said on MSNBC that Ms. Whitmer’s appearances with Mr. Trump, while part of her job as governor, will haunt her.

“The moment you start explaining why you were there in the Oval Office with the president of the United States — particularly this president of the United States - you are already in trouble,” Mr. Capehart said.

During an Oval Office meeting in early April, Ms. Whitmer seemed to realize her misstep.

She held a blue folder over her face in a bizarre and futile effort to ruin photographs of her appearance at a confab with the president. The image was blasted around social media, triggering all sorts of chatter about her political instincts and decision-making.

“President Trump is incredibly good at using Democrats for his own political purposes, while at the same time hurting them,” Mr. Capehart said.