Her critics also raise concern about her longtime leadership of the city’s civil-asset-forfeiture program, which allowed police to seize cash and property from citizens suspected, but not yet convicted, of a crime. Under Grossman, law enforcement seized and spent millions of dollars from residents later found to be innocent. “Should experience really be considered the No. 1 asset for a new prosecutor when that experience is morally compromised?” Philadelphia Daily News and Inquirer writer Will Bunch asked in a recent column. Grossman defends her time in charge of the program, saying she used the law to improve the quality of life in neighborhoods blighted by drug trade. “A neighbor called to thank me for getting rid of a drug house next door to him. He told me that he could now sit on his porch again,” she told Philadelphia magazine.

Krasner, meanwhile, faces questions about his capabilities as a potential prosecutor and his capacity to transform an office with a deeply engrained culture. Echoing other critics, the Inquirer board wrote that he doesn’t have the right experience or “mindset” for the position.

“I think that it helps to have experience as a prosecutor if you want to do a good job running a prosecutor’s office, just as running any office is easier if you have a handle on the workings of an organization. And [it] gives you credibility dealing with staff and other stakeholders in the criminal-justice system,” said David Alan Sklansky, a Stanford University law professor who studies the role of prosecutors. Still, there can be an advantage to coming in as an outsider, Sklansky said, because the DA will be better positioned to “make a clean break from past patterns that have not been helpful.”

While DAs have an undoubtedly important role in local criminal-justice systems, they aren’t dictators: The attorneys working under them still have a tremendous amount of discretion in the courtroom—they decide whether to ask judges to set bail, for example, or what charges should be brought against a particular defendant. Office policies can set some boundaries, but they aren’t always strict rules. For a new DA to make substantive changes, staffers have to be reasonably on board with his or her agenda.

In the six months since Krasner won the Democratic primary, rumors have circulated around the courthouse that assistant DAs opposed to his plans will walk if he wins on Tuesday. But if they don’t, Krasner may need to consider weeding them out anyway, said James Forman Jr., a Yale University law professor and proponent of criminal-justice reform. “He’s going to have to move aggressively to replace a lot of hostile actors,” Forman told me. “He’s got to bring in good new people and they can’t all be outsiders.” Anthony Voci, one of Krasner’s informal policy advisers and a former assistant DA in Philadelphia, told me that lawyers with experience and credibility in the office are ready to join Krasner’s team. “I think there will be some surprises when he walks in there the first day [regarding] who walks in there with him,” he said.