Donald Trump announced his third-straight presidential bid Tuesday, just a week after the midterm elections and in the middle of his legal battles.

In 2016, against all odds, Trump first beat his Republican rivals and then narrowly defeated Democrat Hillary Clinton. 

While Trump has managed to gain a base of loyal supporters, many of whom hold positions of authority within the Republican Party, the task ahead of him could be a difficult one this time. 

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Here’s why.

1. When Trump first announced his bid to run for presidency eight years ago, he had a politically clean slate. With no record in office, voters put their hope in his expansive promises. However, some of his prominent failures – from repealing Democratic healthcare reforms to failing in his promises of infrastructure investment – could cause him some trouble. 

2. Trump is currently defending the way he handled the end of his presidency and his role in the January 6 attack on the US Capitol.

As Trump’s supporters waved banners as they ransacked the Capitol and temporarily halted the peaceful transition of power, has not been forgotten especially with the House Committee investigating the 76-year-old’s role in the attack.

The midterm elections last week saw many Republican candidates losing. These included several of those who offered full-throated support for Trump’s refusal to accept the results of the 2020 elections. 

3. Trump is floating in a pool of legal troubles amid his presidential bid. He is currently defending himself against a criminal election-tampering inquiry in Georgia, a civil fraud case in New York, a defamation lawsuit involving a sexual assault allegation, federal probes into his role in the Capitol attack and his handling of classified material following his end of presidency.

4. Trump might have to face off with Ron DeSantis for the Republican nomination. DeSantis just won an overwhelming re-election victory. However, it remains unknown if DeSantis will run, or who else will enter the Republican presidential contest.

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5. Just ahead of Trump’s presidential announcement, a conservative group released a series of polls that showed the former president and Ron DeSantis matchup by double-digits among Republican voters in Iowa and New Hampshire.

DeSantis led by 26 points in Florida and by 20 in Georgia, which has a Senate run-off election in December. However, Trump’s numbers were quite behind on previous surveys. Exit polls from midterms show Trump’s unpopularity.