During his high-profile hush money trial in 2024, Donald Trump reportedly saw a potential jail sentence as a powerful political tool rather than a punishment. According to journalist Alex Isenstadt’s new book, Revenge: The Inside Story of Trump’s Return to Power, the former president believed imprisonment could rally his supporters and boost his 2024 election chances.
The book details Trump’s mindset throughout the trial, including his frustration with the case, his behind-the-scenes courtroom strategy, and even the prison jokes made at his expense.
Trump’s Trial Strategy: A Political Battlefield
Trump’s legal troubles stemmed from a $130,000 payment to adult film actress Stormy Daniels during his 2016 campaign. Prosecutors argued he falsified business records to cover up the payment, leading to 34 felony charges.
As the trial progressed, Trump grew increasingly convinced he had little chance of winning in a New York City courtroom. He reportedly told aides that the jury was unlikely to be sympathetic and saw the entire ordeal as a “PR battle” rather than a legal fight.
His campaign team transformed the courthouse into a temporary operations center, with live video feeds, political meetings, and even fundraising efforts continuing amid the proceedings. At one point, Trump’s lawyers tried to challenge the judge, while Trump himself repeatedly defied a gag order by attacking witnesses and prosecutors online.
Trump Considered Jail Time as a Symbol of Defiance
Despite publicly lashing out against the case, Trump privately began embracing the idea of being jailed. He allegedly saw it as an “ultimate act of defiance” that would strengthen his standing with supporters.
According to Isenstadt, Trump viewed himself as a martyr and believed his imprisonment could fuel his campaign. He reportedly told aides, “I’m willing to do it. There’s nothing they can do to me that isn’t worth it for the country.”
However, not everyone around him took the idea seriously. A close associate even joked that he could end up as a fellow inmate’s “girlfriend” if he went to prison. Trump, however, did not find the remark amusing.
As the trial reached its final weeks, Trump faced increasing legal pressure. Prosecutors presented evidence tying him directly to the payments, while the defense argued he had little involvement. He continued to violate the court’s gag order, prompting warnings from the judge about possible jail time.
On May 29, after deliberating, the jury found Trump guilty on all 34 counts. Despite his conviction, the judge issued an unconditional discharge, meaning Trump avoided jail time and fines.
With his legal troubles behind him, Trump quickly shifted his focus back to his 2024 campaign, continuing to frame himself as a political outsider fighting against a biased system.

Luis Gochoco is a seasoned managing editor and writer with over a decade of experience covering politics, technology, gaming, and entertainment news. With a keen eye for breaking stories and in-depth analysis, he has established himself as a trusted voice in digital journalism. Luis is one of the key forces behind the success of GameNGuide, contributing to 12 million views through engaging and high-traffic content. He also played a pivotal role in generating 8 million views on International Business Times, shaping the platform’s technology and gaming coverage.
Discover more from Today's Esquire
Subscribe to get the latest posts sent to your email.