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As the 2024 election approaches on November 5, former President Donald Trump faces a critical juncture: a potential return to the Oval Office or the continuation of multiple criminal court proceedings that could possibly lead to incarceration. Throughout his third presidential campaign, Trump has been dealing with four separate criminal cases—two of which have been erratic, one nearing dismissal, and another advancing swiftly towards a potential conviction.

In May, a unanimous jury found Trump guilty of 34 felony counts for falsifying business records. The focus of the seven-week trial was a scheme executed during his presidency, involving the concealment of a $130,000 payment made to an adult film star to prevent her from revealing a past affair. This payment occurred just days before the 2016 election. The consequences of these actions will be disclosed shortly after the 2024 election, with sentencing set for November 26. Although the sentencing was initially scheduled for July 11 and postponed to September, former New York prosecutor and Pace University law professor Bennett Gershman sees no legal reason for any further delay, even if Trump wins the election.

Gershman explains that if Trump loses and is sentenced to jail, the appeal process could delay incarceration for years. Conversely, a presidential win could further delay both the appeal proceedings and the sentence until after his term. "A president with 34 felony convictions running the nation is something unprecedented," Gershman remarked.

Special counsel Jack Smith brought a significant case against Trump in August 2023, charging him with four counts related to efforts to overturn the 2020 election results. Although Trump's claim of presidential immunity initially stalled the case, the Supreme Court's July ruling provided a new framework, resulting in a narrowed superseding indictment in August.

Smith is also managing another case in Florida, where Trump faces accusations of mishandling sensitive government records post-presidency. U.S. District Judge Aileen Cannon dismissed the case in July, citing Smith’s unlawful appointment, but Smith's office has since appealed this decision. Trump’s legal team argues that Cannon's decision should also lead to the dismissal of the election-related case.

Legal analysts, including CBS News's Rikki Klieman, suggest that if Trump wins the presidency, his administration’s Justice Department would likely drop the charges. Trump has openly stated that he would immediately fire Smith if elected, underscored in an October 24 radio interview.

In another significant development, Trump was charged in a state case in Georgia in August 2023, alleging involvement in a racketeering enterprise aimed at overturning his election defeat in the state. Although five of the 13 charges were dismissed, Fulton County D.A. Fani Willis is appealing the dismissals of three charges and likely more. Nevertheless, the case has been on hold since June due to pending considerations by the state's Court of Appeals regarding Willis’s relationship with former special prosecutor Nathan Wade.

Emory University law professor John Acevedo notes that a Trump victory would effectively pause the Georgia case due to logistical difficulties with having a sitting president in court. Trump's lead attorney in Georgia, Steve Sadow, has echoed this sentiment, arguing that under the Constitution’s Supremacy Clause, any trial related to this case would have to be delayed until Trump's term ends, potentially in 2029.

As Election Day approaches, the outcome will not only shape the nation's political landscape but will also determine the immediate future of Donald Trump's legal battles.