Trump has complained publicly and privately that his first-term Justice Department leaders were too weak, that his Supreme Court picks have tried to come across as too “independent” and that the court system has broadly been biased against him, as he faces 91 felony charges. Trump told donors in meetings in late 2023 that one of his only mistakes as president was that he did not pick the right people to lead the Justice Department, according to people who attended, and he regularly discusses plans for the department in a second term. In some ways, the handshake agreement he once held with the traditional conservative legal movement has evaporated.

“They were intellectually qualified for the most part to become judges,” said former White House lawyer Ty Cobb, who has since become a Trump critic, speaking of Trump’s first-term appointees. “I don’t think there’s a chance that will be the case in a second term.”

Trump has more broadly gravitated away from the GOP establishment he has long derided but learned to work with in his term as president. The implications of his shift could be significant - from potentially imperiling a long-observed firewall between the White House and the Justice Department, to appointing lawyers in his administration willing to approve novel approaches to the law and dare courts to stop them, to shifting the nation’s courts further to the right.

The former president will be looking for appointees “who are talented and strong and - here’s the key ingredient - truly committed to helping him accomplish his agenda,” said Mark Paoletta, former general counsel of the Office of Management and Budget under Trump.

Too many people in the last administration, Paoletta said, “actually disagreed with the president and tried to thwart him.” He noted: “You don’t want fair-weather appointees in your administration,” and, “your lawyers should be as aggressive as possible to help the president carry out his agenda.”

When Trump first ran for the White House, prominent members of the Federalist Society gave him the names of hundreds of prospects to nominate for the federal bench and worked with him to create a list of potential Supreme Court justices that he promoted publicly. In office, Trump drew from that roster and other recommendations to stock his administration with their allies, shift the high court to the right and appoint hundreds of other federal judges. He claimed credit for landmark conservative victories such as the Supreme Court overturning Roe v. Wade, which had established a constitutional right to abortion.

Trump now rails against the Federalist Society privately, according to advisers. He no longer speaks to many lawyers who were once instrumental, including former Federalist Society leader Leonard Leo, former White House counsel and Federalist Society board member Donald McGahn, or Senate Minority Leader Mitch McConnell (R-Ky.) - the triumvirate who propelled much of his judicial record in the first term.

People close to all three men, who like others spoke on the condition of anonymity to be more candid, said they have concerns about Trump winning again but are loath to fight him publicly. Similarly, many in the conservative legal movement who have backed away from Trump are reluctant to speak out against him, and some have even expressed openness about working in a second Trump administration, sparking a larger debate in the movement about whether to do so, interviews show.

Trump has recently floated combative lawyers from outside the traditional legal establishment who go on television to defend him, such as Mike Davis, as top attorney general candidates for a second term, telling advisers and donors that his picks for the job were a mistake in the first term because they were weak or defied him. Davis has faced criticism for his comments about imprisoning journalists and caging children if he became attorney general, comments which he said were made in jest.

In an interview, Davis, president of the Article III project, a conservative judicial advocacy group, said, “President Trump’s next generation of judges will be even more bold and tough.”

Others, including former Trump Justice Department official Jeffrey Clark, one of six unnamed co-conspirators referred to in Trump’s indictment in a federal election interference case, are at the center of informal discussions about a second term, prompting some alarm in conservative legal circles.

The former president’s actions on Jan. 6, 2021, when a pro-Trump mob stormed the U.S. Capitol, left some conservative lawyers - who resolved to reap the benefits of Trump’s presidency while ignoring many of his excesses - believing he had gone too far. Some said they also are concerned that Trump will be convicted of felonies before he can become president.

A spokesman for Trump did not respond to multiple requests for comment. A spokesman for McConnell declined to comment. McGahn did not return a request for comment.

Leo said he felt Trump would continue to nominate conservative judges who interpret the meaning of the Constitution as it was written because he does not have much of a choice. He has told others he no longer talks to Trump’s advisers and is largely focused on spending billions to reshape the country in a more conservative direction with a focus on non-election issues.

“I can’t see a situation where Donald Trump doesn’t pick originalist judges if he gets a second term, because the Federalist Society has won the philosophical debate, and the current court is now upholding the rule of law and the Constitution more than at any other time in modern history. This remains a clear and necessary path for victory for any Republican,” Leo said.

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Frayed alliances

Trump’s 2016 campaign and first term in the White House received a boost from an enthusiastic push on the right for conservative judges and deregulation - with many willing to overlook other concerns about Trump in pursuit of those goals.

Under the Trump administration, the GOP-controlled Senate confirmed 174 district court judges, 54 circuit court judges and three Supreme Court justices - shifting the balance of the highest court to a 6-3 conservative majority. During his campaign rallies and events, Trump often likes to highlight the total, though he has exaggerated it.

In a 2022 interview with The Washington Post, McConnell recalled that Trump’s first candidacy had worried many conservatives at the time but that his Supreme Court list and picks had calmed their nerves and that his bargain with Trump had moved the country “right of center.”

That bargain has frayed in key ways since Trump left office.

Trump and Leo, a prominent conservative lawyer influential in his first term, have not spoken since 2020, according to people familiar with the matter. Their relationship ended over a heated fight in 2020 at Mar-a-Lago, where Trump accused Leo of picking Rod J. Rosenstein to be deputy attorney general, a person familiar with the matter said. Trump’s anger around Rosenstein centered on his decision to appoint special counsel Robert S. Mueller III to oversee the Justice Department’s probe of Russian interference in the 2016 election. A person close to Leo said he did not recommend Rosenstein for the job.

McConnell and Trump have not spoken since late 2020, and Trump has repeatedly called for McConnell to be removed as the GOP leader of the Senate.

Most members of the Federalist Society board of directors declined to comment on the record or did not respond to a request for comment. Interviews with a dozen other prominent lawyers suggested most had serious misgivings about Trump returning to power but were resigned to the high likelihood he will be the nominee, and many expressed openness to working for another Trump administration.

Others described a president with a transactional view of judges but noted that the Senate would still need to confirm his nominees, offering a backstop for those who are unqualified or too extreme. Senators also have significant influence over their home-state lower court judicial nominees.

“He’s the leading candidate, so I don’t know that it matters what I think,” said Brent O. Hatch, a lawyer who is on the board of the Federalist Society.

Even while he was in the White House, Trump grew frustrated with some judicial nominees his allies recommended to him and whose decisions he disagreed with, according to one person familiar with Trump’s dynamic with the Federalist Society. He also thought that Leo took too much credit for his judicial record, this person said.

In the first Trump term, Leo, McConnell and White House lawyers learned that he usually accepted the names they brought him and liked to brag about his record number of appointees, according to people familiar with the White House dynamics.

“I think he became convinced that what we were doing was quote successful,” McConnell said in a 2022 interview, describing Trump as “frequently at war with his own advisers.”

As he runs for another term, Trump talks about judicial issues in less detail than he did during his first run. His unwillingness to speak about the Supreme Court and conservative judicial issues has concerned some allies. The former president talks less frequently than he once did about judges and does not plan to make judges a centerpiece of his campaign, campaign advisers say, even though conservatives view the topic as one of his most substantial accomplishments and one that motivated many of his supporters in 2016. He has not issued a new list of potential nominees.

Although Trump reshaped the Supreme Court while in office, leading to the overturning of Roe, he has sometimes told others that the decision is a political albatross for Republicans. And he has complained recently at rallies about the Supreme Court and the decisions the judges make, saying without evidence they rule too often against Republicans to show “independence.”

“My expectation is he’s going to do exactly what he did his first term, and he should do that and he should talk about it more during the campaign and if he’s got other names that he’s thinking about or taking names off, he should put out a new list,” said Sen. Chuck Grassley (R-Iowa), who was chairman of the Judiciary Committee during Trump’s first two years in office.

Ralph Reed, chairman of the Faith and Freedom Coalition, said that releasing a list of potential judicial nominees as he did in his first run would be a good move for Trump and that the former president should tout his record on remaking the judiciary because it was a high priority for conservatives.

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New tensions over a second Trump term

Trump is running on a campaign focused, at least in part, on vengeance and retribution. The former president has made it clear that loyalty would be a key criteria in how he makes decisions if returned to office.

Trump has signaled that he wants the Justice Department to go after his political opponents, and his associates have drafted plans to invoke the Insurrection Act on his first day in office, which would allow him to send the military against civil demonstrations. Near the end of his time in the White House, he repeatedly complained that his White House Counsel’s Office wasn’t doing enough to help him overturn the election results. His attorney general resigned after he would not back up his claims.

There is a heated debate underway in conservative legal circles about how GOP lawyers should interact with what increasingly appears to be the likely nominee, according to conservative lawyers who described the private talks on the condition of anonymity. The discussions include whether they would return to work for Trump.

One prominent lawyer described a November dinner he attended where almost all the attorneys in the room said they would prefer another nominee - but were split on whether to back Trump if he wins. Another prominent Washington lawyer described debates at a Federalist Society meeting about what it would be to work inside again and whether they would populate the agencies.

At the heart of that debate is an aversion by many of Trump’s advisers toward attorneys they view as institutionalist Republican lawyers.

Leo, McConnell and McGahn have expressed reservations about what another Trump term would look like, though they have largely stayed away from a public fight.

Some of the informal conversations and debates underway in conservative legal circles about a second Trump term include Project 2025, a coalition of right-wing groups that has outlined plans for the next Republican administration. Clark, who is working on the Insurrection Act for Project 2025, has been charged with violating Georgia’s anti-racketeering law, in the case alleging Trump and co-conspirators of interfering in the 2020 election. Clark has pleaded not guilty.

The involvement of Clark with that effort has alarmed some other conservative lawyers who view him as a potentially disastrous choice to take a senior leadership role at the department because of his past activities around the 2020 election. A representative for Clark did not respond to a request for comment.

Despite the swirling concerns, some attorneys on the right do not expect a public outcry against Trump, noting that many have often fallen in line behind him. Rob Kelner, a prominent conservative lawyer, said more conservative lawyers should have spoken up against Trump, but that it would cost them business and relationships.

“There were so many positions he took and so many statements that he made that flatly contradicted the foundational principles of the conservative movement and the Federalist Society, and yet it was so rare to hear conservative lawyers speak out against Trump,” Kelner said.

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Devlin Barrett contributed to this report.