As a federal prosecutor in the 1990s, Andrew Weissmann persuaded mobsters to break the Mafia code and testify against their brothers in crime, winning a conviction against Genovese family boss Vincent “the Chin” Gigante.

Later, as he headed the Justice Department’s Enron task force, his ability to persuade key witnesses to testify about what they saw on the inside helped secure a series of convictions.

Now Mr. Weissmann is part of the all-star team that former FBI Director Robert Mueller has put together as the special counsel pursuing a look into Russian meddling in the November presidential election and suspected collusion with Trump campaign figures — a case legal analysts say is brimming with the potential for cooperators.

Ten of the 12 lawyers on Mr. Mueller’s team have been revealed, and their political leanings have sparked early controversy. At least five have donated to Democratic campaigns.

But analysts say the team is full of legal stars, including Mr. Weissmann, who have the skills and experience to handle the investigation fairly — wherever it leads.

They include a former Watergate prosecutor, an experienced Supreme Court litigator, a former FBI counterterrorism agent, a prosecutor with experience in organized crime cases and the head of the Justice Department’s public corruption unit in Manhattan.

Recruiting team members with experience probing financial cases or who are familiar with national security protocol will be essential. Mr. Mueller appears to have both covered, said lawyer Philip Lacovara, who was part of the Watergate special prosecutor’s team.

“Anybody who has done financial crimes investigations knows sometimes you start an investigation and you determine there is nothing there. But the key is having people who know what to look for,” he said. “It’s the idea that they have people with experience in big document cases that suggests to me this will be a serious investigation.”

Stretching the law

Mr. Weissmann and Deputy Solicitor General Michael Dreeben, who has argued more than 100 cases before the Supreme Court, each had a hand in an obstruction of justice case that some legal scholars say may illustrate an aggressive approach by Mr. Mueller in the Russia investigation.

As director of the Justice Department’s Enron probe, Mr. Weissmann oversaw the 2002 prosecution of the accounting firm Arthur Andersen, which was found guilty of obstruction after employees were told to shred documents related their energy company client.

After cutting his teeth prosecuting organized crime cases in Brooklyn, legal analysts say, Mr. Weissmann brought to the table experience flipping witnesses that helped him secure the star witness in the Andersen case: former Enron financial officer Andrew Fastow, who testified against his former bosses Kenneth Lay and Jeffrey Skilling.

On appeal before the Supreme Court, it was Mr. Dreeben who defended the government’s position that the company knowingly committed a crime by invoking its document retention policy “as a pretext and cover to clean up and purge the files.”

The Supreme Court ultimately sided with the accounting firm and overturned the conviction, remanding the case back to a lower court.

After the legal spanking, the Justice Department dropped the matter. But the highly publicized prosecutions established Mr. Weissmann and Mr. Dreeben as attorneys who would push the limits on difficult cases.

“These are two federal prosecutors who are known to stretch the criminal code to its breaking point,” said George Washington University law professor Jonathan Turley.

That is relevant to the Russia investigation, he said, because of the hurdles the special counsel team is likely to face.

As part of the Russia probe, the special counsel’s team is reportedly considering whether Mr. Trump attempted to obstruct justice by firing FBI Director James B. Comey, who had been overseeing the investigation.

A long-standing opinion of the Justice Department’s office of legal counsel holds that a sitting president can’t be criminally charged, leaving Mr. Mueller to decide whether or not his team is bound by the legal interpretation.

“I don’t see how a case could be brought on this evidence without pushing both the precedent and the language of the law to the far extreme,” Mr. Turley said. “If you are going to charge the president, you should find a clear criminal violation that is in the center of the strike zone. Both Dreeben and Weissmann are used to throwing at the corners to bring charges.”

Mr. Lacovara, though, said he expects Mr. Mueller’s team will be “careful and cautious rather than aggressive and reckless” given the public sensitivity of the investigation.

Based on his wealth of experience, Mr. Dreeben’s role in the investigation will likely be “to offer hardheaded analysis of what the law is rather than to argue for expansion of the law,” Mr. Lacovara said.

Donations to Democrats

Former House Speaker Newt Gingrich, a top ally of the president, has been critical of those hired for the team because of their political contributions.

At least five members of the team have donated to Democrats in recent elections, according to records from the Center for Responsive Politics.

“Republicans are delusional if they think the special counsel is going to be fair,” Mr. Gingrich wrote on Twitter last month.

Mr. Trump told Fox News last month that it was ridiculous to have Hillary Clinton supporters as members of the investigative team.

Among the donors are Jeannie Rhee, a former deputy assistant attorney general for the Justice Department’s office of legal counsel, who donated $5,400 to Mrs. Clinton’s presidential campaign PAC Hillary for America. She gave $4,800 to President Obama’s campaign.

While working at the WilmerHale law firm with Mr. Mueller, Ms. Rhee was on the legal team that represented the Clinton Foundation. She was also part of the team that defended Mrs. Clinton against lawsuits over her email practices as secretary of state.

She worked alongside high-profile Democratic lawyer Jamie Gorelick, who now represents Ivanka Trump and Jared Kushner, the president’s daughter and son-in-law.

Earlier in her legal career Ms. Rhee, a former assistant U.S. attorney, successfully prosecuted Washington Teachers Union officials who embezzled nearly $5 million.

Mr. Weissmann, while helping lead the white-collar defense team Jenner & Block law firm in 2006, donated $2,000 to the Democratic National Committee. In 2008, he gave $2,300 to the Obama campaign.

Watergate prosecutor James L. Quarles III, who has worked at WilmerHale since the mid-1970s, has a more bipartisan donation record, though his roughly $20,000 in contributions over the past few decades skews toward Democrats at the presidential level. He gave to failed Democratic nominees Michael Dukakis and Al Gore.

Elizabeth Prelogar, an appellate lawyer from the solicitor general’s office who studied in Russia on a Fulbright scholarship, gave $250 to the Hillary for America Political Action Committee and in 2012 donated $250 to Mr. Obama’s campaign.

Andrew Goldstein, a federal prosecutor who headed the Justice Department’s public corruption unit in Manhattan, gave $750 to Mr. Obama’s campaign in 2012.

No recent donations were on file for Mr. Mueller, a registered Republican. In 1996, Mr. Mueller did donate $450 to William Weld, the Republican candidate for a U.S. Senate seat from Massachusetts. Mr. Mueller worked for Mr. Weld when he was the U.S. attorney in Boston.

The special counsel’s office has defended the hires and said it is following Justice Department policy and federal law that “prohibit the use of political or ideological affiliations to assess applicants.”

Mr. Turley, though, said he was surprised at how many lawyers Mr. Mueller brought on with histories of left-leaning political contributions.

“It’s not that it’s unethical, but when you are investigating a president and his administration it’s incumbent upon you to assure the public that political bias and affiliation will not factor into decision-making,” said Mr. Turley said. “Washington, D.C., has tens of thousands of lawyers. You can throw a stick on any corner and hit 10 of them.”

Richard Painter, a White House ethics counsel under George W. Bush, said prosecutors aren’t neutral to begin with and stressed that it’s judges who ultimately make legal determinations.

“If campaign contributions are a problem, U.S. attorneys wouldn’t be political appointees,” he said. “Hiring people who have the ability and the skill, that’s what is key.”

Experience matters

Several of the members of the special counsel’s team have expertise in handling appeals, something that could hint at Mr. Mueller’s long-term preparations. Mr. Dreeben’s record of arguing cases before the Supreme Court is particularly striking.

“It may be that he’s lining Dreeben up because he anticipates needing Dreeben’s services so that he can handle the investigation in a way that can handle appellate scrutiny or Dreeben may end up handling some appeals,” said Kathleen Clark, an ethics law professor at Washington University in St. Louis.

Ms. Prelogar also comes from the solicitor general’s office, and Adam Jed, an appellate attorney in the Justice Department’s civil division, has argued civil cases across the country — including defending the Obama administration’s contraceptive coverage policies before the 10th U.S. Circuit Court of Appeals.

Having experience on high-profile cases could help the lawyers prepare for the outsized attention they are likely to face as the investigation proceeds.

“You just have to put on some sort of armor to get the job done,” said John Curran, a former assistant U.S. attorney in the Eastern District of New York who worked early on in his career with Mr. Weissmann. “Whether it’s the powerful people you are looking at, or the fact the president is trying to comment on the case every day, you could see people getting swept up in ‘Oh I’m on a cool case’ and that’s not Andrew.”

Known for his penchant for keeping information close to the chest, Mr. Mueller has also sought to recruit known quantities.

Former FBI counterterrorism agent Aaron Zebley, who was Mr. Mueller’s chief of staff at the FBI, also worked at his law firm WilmerHale before leaving to join the new probe. Mr. Quarles and Ms. Rhee were also WilmerHale lawyers. Mr. Weissmann also previously served as both special counsel and general counsel in the FBI.

Rounding out the known members of the team are Lisa Page, a prosecutor with experience in organized crime cases, and Aaron Zelinsky, an assistant U.S. attorney who worked in Maryland under Deputy Attorney General Rod Rosenstein, who opted to appoint Mr. Mueller as special counsel to lead the probe.

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