WASHINGTON – Donald Trump enjoys poking fun at others, but he isn’t fond of being the target of jokes—especially regarding his criminal history.

Throughout his week-long campaign designed to respond to the Democratic convention, Trump has found himself on the defensive. In Chicago, numerous speakers have ridiculed the GOP nominee for various reasons, including his fascination with crowd sizes, his perceived eccentricity, and, most notably, his significant legal issues stemming from a conviction in a hush money case in New York.

“Did you see Barack Hussein Obama taking jabs last night?” Trump asked his supporters during a national security speech at the North Carolina Aviation Museum & Hall of Fame on Wednesday, referring to his predecessor. “He was quite mean-spirited last night. I usually try to be nice, but it gets tricky when they go personal.”

In his speech where he endorsed Kamala Harris as the new Democratic nominee, Obama criticized Trump’s political history as filled with complaints and grievances, stating, “This has only intensified because he feels threatened by Kamala. The childish names, bizarre conspiracy theories, and the strange fixation on crowd size, It just doesn’t stop.”

Speakers at the convention, including some Republicans, have concentrated their remarks on Trump’s numerous legal challenges, particularly his May conviction in the New York case. U.S. Representative Jasmine Crockett, a Democrat from Texas, noted, “Kamala Harris comes with an impressive resume, while Donald Trump lists a ‘rap sheet.’” Additionally, at the United Center, attendees took selfies with Michael Cohen, Trump’s former attorney who testified against him during the Manhattan trial.

Trump has indicated that his advisors suggest he focus on policy instead of personal attacks, but he doesn’t always follow that advice. In his speech, he humorously remarked, “I don’t know, my advisers are fired. But, yes, we’d prefer to keep things policy-focused yet it can be challenging when you are under attack.”

‘Convicted felon’

Trump’s team has said he is not pleased with being labeled a “convicted felon,” though he acknowledges it’s not unexpected.

In Trump’s circle, the legal challenges brought up at the Democratic convention are viewed as another example of what they describe as the “weaponization” of the legal system against him. They assert—without evidence—that law enforcement pursued four different indictments against Trump in 2023 to influence the upcoming 2024 election.

The Chicago convention ultimately reflects “more baseless personal attacks from outdated Democrats who lack any real solutions for the issues everyday Americans encounter,” remarked Steven Cheung, a spokesperson for Trump’s campaign.

In a public safety address on Tuesday in Michigan, Trump accused Democrats of being weak on crime, saying, “They target people like me, but they ignore those who actually commit violence.”

Trump and his team maintain that the legal troubles he faces won’t significantly affect voter sentiment in the lead-up to the election in two and a half months. They believe numerous voters share his view that the prosecutions are politically motivated.

Cheung stated, “People understand it’s a biased justice system trying to interfere in an election.”

‘Don’t get personal’

In addition to the legal concerns, Trump and his aides have critiqued what they see as the media’s overly positive portrayal of Harris and her presentation at the convention.

At one moment in North Carolina, Trump chastised his political advisors for advising him to remain focused on policy and avoid personal attacks, particularly given that his opponents often engage in personal jabs against him.

“They’ve been personal all night, those folks,” Trump said. “Should I stick to policy?”

Later, he expressed the same sentiment, asking the North Carolina audience whether he should target his Democratic critics personally; the crowd responded enthusiastically in support, despite Trump’s long history of personal comments.

While Trump and his team claim they are unconcerned about the election-related implications of their legal troubles, many political analysts fear these challenges could negatively impact his appeal to undecided voters.

On September 18, just over a week after his initial debate with Harris, Trump is set to be sentenced in the hush money lawsuit. Back in late May, a jury in New York found Trump guilty on 34 counts of falsifying business records to conceal payments related to an affair with an adult film actress. (In her address, Crockett referred to Trump as “a career criminal” with 34 felonies, two impeachments, and one porn star.)

Judge Juan Merchan from New York has the option to impose a prison sentence, though it is quite unlikely that Trump would be incarcerated in the near future. He is currently appealing the verdict and will remain free while that appeal is underway.

For months, Trump has criticized the prosecution, telling his supporters on Wednesday that “they want to put you in jail for nothing.”

Additional Legal Matters

Trump and his team assert that they feel victorious regarding legal challenges.

Previously, Trump was looking at four trials prior to the Election Day on November 5. Although the New York case is progressing, he currently faces no trials during the final phase of the presidential campaign, although some pre-trial motions may take place.

Earlier in July, the U.S. Supreme Court ruled that former presidents cannot be prosecuted for actions taken in their official capacity. This significant ruling has delayed a federal case accusing Trump of attempting to disrupt the 2020 election, which led to the January 6, 2021, insurrection.

A federal judge must now determine whether the allegations against Trump pertain to official acts. This may lead to hearings in September and/or October, coinciding with the campaign period.

There is another similar case regarding election interference pending in Georgia, but it has been delayed due to preliminary legal strategies.

Trump’s attorneys successfully had a fourth case against him thrown out. A federal judge in Florida dismissed an indictment accusing Trump of mishandling classified documents, although the government is appealing that ruling.

‘Lock Him Up’

Hillary Clinton, the former first lady who lost the 2016 election to Trump, blended ridicule with a legal assessment during her speech at the convention, reminding Democrats that Trump dozed off during parts of the hush money trial. “And when he woke up,” Clinton remarked, “he made a unique kind of history – being the first candidate to run for president with 34 felony charges.”

Democratic delegates excitedly chanted “lock him up,” echoing the slogan used by Trump’s supporters against Clinton during the 2016 election.

In response, Trump claimed he had the power to imprison Clinton when he was president but chose not to exercise that authority.

Trump sharply criticized Kathy Hochul, the governor of New York, calling her “the meanest speaker” at the convention’s opening night.

In her address, Hochul asserted that Trump does not embody American values, stating, “Donald Trump was born a New Yorker, but he has become a fraud, a philanderer, and a felon.”