NEW YORK (AP) — When he was elected two years ago as Manhattan’s first Black district attorney, Alvin Bragg spoke candidly about his unease with the job’s political demands. A former law professor, he’s more comfortable untangling complex legal questions than swaggering up to a podium.

But when the first of Donald Trump’s four criminal prosecutions heads to trial on Monday, about alleged hush money payments to cover up a sex scandal during the 2016 election, Bragg will be at the center of a political maelstrom with few precedents.

Even before announcing the 34-count felony indictment against Trump last year, Bragg was a lightning rod for conservative critics who said he wasn’t tough enough on crime. The upcoming trial will test the Democrat’s efforts to portray himself as apolitical in the face of relentless attacks from the Republican former president and his supporters, who say the prosecution is the epitome of partisanship.

Echoing the racist tropes he has deployed frequently against his legal adversaries, Trump has called Bragg a “thug” and a “degenerate psychopath,” urging his supporters to take action against the “danger to our country.”

Bragg, who declined to be interviewed for this story, has rejected that, comparing the prosecution against Trump to any other case of financial crime.

“At its core, this case today is one with allegations like so many of our white collar cases,” Bragg said in announcing the indictment last year. “Someone lied again and again to protect their interests and evade the laws to which we are all held accountable.”

The first-ever trial of a former U.S. president will feature allegations that Trump falsified business records while compensating one of his lawyers, Michael Cohen, for burying stories about extramarital affairs that arose during the 2016 presidential race.

The charges — which carry the possibility of jail time — threaten Trump’s campaign schedule as he faces a general election rematch with President Joe Biden.

They have also turned a spotlight on Bragg, who since bringing the indictment has been the target of scores of racist emails and death threats, as well as two packages containing white powder.

“Because he is the first to get Trump to trial, and because he’s been successful so far, the level of hate pointed at Bragg is staggering,” said Norman Eisen, a senior fellow at the Brookings Institution who served as special counsel in the first impeachment trial against Trump. “The threat level is just off the charts.”

Citing Trump’s threatening and inflammatory statements, Judge Juan M. Merchan imposed a gag order last month that bars Trump from publicly commenting on witnesses, jurors or others involved in the case — though not Bragg or the judge personally. Attorneys for Trump have sought to reverse the order, seizing on the issue as one of several arguments for delaying the trial.

The 50-year-old Harlem-raised Bragg got his early political education during visits to the city’s homeless shelters, where his father worked. He said he was held at gunpoint six times while growing up — three times by overly suspicious police officers — and once had a knife held to his throat.

After graduating from Harvard Law School, Bragg began his career as a criminal defense and civil rights lawyer, later joining the federal prosecutor’s office in Manhattan. As a top lawyer in the New York attorney general’s office, he oversaw investigations into police killings and a lawsuit that shut down Trump’s charitable foundation.

Though he said he had little interest in elected office, Bragg joined a crowded race for Manhattan district attorney in 2019, running on a platform of “justice and public safety.”

Compared to many of his opponents, Bragg took a more measured tone in detailing his plans for the investigations into Trump and his businesses, which began under former District Attorney Cyrus Vance Jr.

Once in office, Bragg surprised many by pausing the criminal investigation into Trump, leading to the resignation of two top prosecutors who had pushed for an indictment.

When he resurrected the case last April, the charges of falsifying records were raised to felonies under an unusual legal theory that Trump could be prosecuted in state court for violating federal campaign finance laws. Some legal experts say the strategy could backfire.

“It seems a bit of a legal reach, and the question is why are they doing it?” said Jonathan Turley, a professor at the George Washington University Law School. “It can be hard to escape the conclusion that this effort would not have been taken if the defendant was not Donald Trump.”

Others have blessed the legal theory, including a federal judge, Alvin Hellerstein, who wrote in a decision last year that the law did not provide exceptions for election-related activities.

From his first days in office, Bragg found himself under a barrage of criticism over a memo instructing prosecutors not to seek jail time for some low-level offenses.

He walked back portions of the directive amid fierce protest from New York Police Department leaders, conservative media and some centrist Democrats, though he later said he regretted not pushing back more forcefully. For many on the right, the image of Bragg as a poster child for Democrat permissiveness stuck.

“When you’re the district attorney, you are also a politician, and there’s been a slight failure to grasp that,” said Rebecca Roiphe, a New York Law School professor who taught alongside Bragg and previously worked in the Manhattan district attorney’s office. “The fact that he’s not attuned to what he needs to do politically to get things done is both a strength and a weakness.”

Though most major crime rates in Manhattan remain lower than before Bragg took office, conservatives continue to accuse him of allowing rampant lawlessness. Republicans convened a congressional field hearing in New York to examine what they said were Bragg’s “pro-crime, anti-victim” policies.

Bragg was pilloried on the right again earlier this year when he declined to seek pretrial detention for some men accused of brawling with police officers in Times Square.

The decision sparked criticism not only from conservatives but also Gov. Kathy Hochul, a Democrat, and top NYPD officials. Bragg defended himself, telling reporters, “the only thing worse than failing to bring perpetrators to justice would be to ensnare innocent people in the criminal justice system.”

He later announced several men initially arrested played only a minor role or were not present at all.

In 2022, Bragg’s office pressured the Trump Organization’s longtime chief financial officer, Allen Weisselberg, into pleading guilty to evading taxes on company perks like a luxury car and rent-free apartment. Later that year, it put Trump’s company on trial, and won a conviction on similar tax charges.

After that, Bragg convened a new grand jury, securing the indictment accusing Trump of falsely recording payments to Cohen as legal expenses, when they were for orchestrating payoffs to porn actor Stormy Daniels and former Playboy model Karen McDougal, to prevent them from going public with claims they had extramarital sexual encounters with Trump.

Trump denies the accusations and says no crime was committed. Now, a jury is on the verge of being picked that will make a historic decision about whether Trump broke the law — or Bragg overreached.