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WASHINGTON—Special counsel Jack Smith has all but finished obtaining testimony and other evidence in his criminal investigation into whether former President Donald Trump mishandled classified documents at his Mar-a-Lago resort, according to people familiar with the matter.

Some of Trump’s close associates are bracing for his indictment and anticipate being able to fundraise off a prosecution, people in the former president’s circle said, as clashes within the Trump legal team have led to the departure of a key lawyer.

In recent weeks prosecutors working for Smith have completed interviews with nearly every employee at Trump’s Florida home, from top political aides to maids and maintenance staff, the people said. Prosecutors have pressed witnesses—some in multiple rounds of testimony—on questions that appeared to home in on specific elements Smith’s team would need to show to prove a crime, including those that speak to Trump’s intentions, and questions aimed at undermining potential defenses Trump could raise, they said.

The special counsel team conducted a flurry of grand jury interviews in recent weeks that appeared to tie up loose ends, the people said.

The Journal couldn’t determine whether Smith has decided whether to charge Trump, or if he has presented a recommendation on the matter to Attorney General Merrick Garland, who would ultimately make a final decision on any such charges. A spokesman for Smith declined to comment. A Trump spokesman didn’t immediately respond to a request for comment but has previously described the probe as a politically motivated witch hunt.

Smith’s team, which has been examining whether anyone tried to obstruct the criminal inquiry, has obtained evidence that appears to show Trump held on to sensitive documents after being asked to relinquish them, the people said. Last week the National Archives turned over to Smith’s team records of communications between then-President Trump and some of his advisers about how he could declassify documents, some of the people said, material that could help prosecutors overcome the defense that Trump believed he could do so verbally. CNN first reported the National Archives transfer.

Smith’s team is still pursuing a separate inquiry into efforts by Trump and his allies to overturn his 2020 election loss.

Any charges, if filed, would come at a politically delicate time, as Trump campaigns for the 2024 GOP presidential nomination and is the front-runner to take on President Biden, who has also announced his bid for re-election.

A separate special counsel has also been investigating how and why classified documents ended up at Biden’s home and office, after he left the vice presidency in 2017.

Earlier this year, Trump became the first former president in U.S. history to face criminal charges, after prosecutors in Manhattan charged him with 34 felony counts of falsifying business records, in connection with hush money Trump paid to a porn star to allegedly bolster his 2016 presidential campaign. Trump has pleaded not guilty and accused the Manhattan District Attorney, Alvin Bragg, a Democrat, of pursuing him for political reasons.

In a letter to lawmakers last month, lawyers for Trump compared the documents found at Trump’s home to those found at Biden’s residence and others found at former Vice President Mike Pence’s home, saying that “deficient document handling and storage procedures are not limited to any individual, administration or political party.” The lawyers called the Justice Department inquiry an example of “ham-handed criminal investigations of matters that are inherently not criminal.”

The letter, which was viewed by The Wall Street Journal, also said some of the boxes with classified material appeared to contain briefing papers related to phone calls Trump was having with foreign leaders. White House staff appear to have just swept up materials from Trump’s desk as they packed, it said.

One of the letter’s authors, Tim Parlatore, said it was part of an effort to dissuade Garland and prosecutors from pressing criminal charges. But the missive, and particularly a push by its authors to publicize it, triggered upheaval within the Trump legal team, according to people familiar with the matter.

Parlatore, who recently withdrew from representing Trump, told The Wall Street Journal he doesn’t believe charges will be brought against anyone in the Mar-a-Lago investigation. He said his departure from the legal team was prompted generally by clashes with Boris Epshteyn, a top Trump adviser who has functioned as in-house counsel for the former president, assisting with hiring lawyers and coordinating legal efforts.

“There are certain individuals that made defending the president much harder than it needed to be,” Parlatore said on CNN on Saturday.

Epshteyn declined to comment.

A Trump spokesman, Steven Cheung, said Parlatore’s “statements regarding current members of the legal team are unfounded and categorically false.”

Parlatore had pushed, during a visit with Trump, to quietly resolve the infighting and limit Epshteyn’s role in the special-counsel inquiry, people familiar with the matter said.

Among some in Trump’s circle, Epshteyn was seen as hindering communication with the former president and as having exposure in the special counsel’s criminal inquiry that could complicate his advice. He has nevertheless continued to advise Trump in a senior role, those people say.

Prosecutors in Smith’s office interviewed Epshteyn during a two-day span in late April, with a focus on efforts by Trump and his allies to overturn the results of the 2020 election, according to people familiar with the questioning.