The questions being posed expose the delicate position any White House lawyers face who are tasked with handling investigations. Inevitably, the work they do often becomes part of the investigation itself. And with the Democratic-led House now launched on an impeachment investigation, it’s the attorneys tasked with representing the presidential side of Trump who also must prepare to be on the receiving end of their own subpoenas.

“It is a legitimate avenue of inquiry in an obstruction investigation,” said Jane Sherburne, a former top White House lawyer who handled President Bill Clinton’s responses to investigations by both Congress and independent counsel Kenneth Starr. “Whether they are in legal jeopardy? It’s hard to know, but certainly there’s a risk, if not a likelihood, that they will be called to testify.”

So far, there are three interrelated issues posing challenges inside the White House counsel’s office, the catch-all location for all government issues dealing with the president and which Cipollone overhauled when he took over late last year.

First, there’s the whistleblower complaint released on Thursday. It describes a July phone call in which Trump asked the new Ukrainian president, Volodymyr Zelensky, to investigate former Vice President Joe Biden, the 2020 Democratic front-runner, and reopen an inquiry into Russia’s meddling in the 2016 election. White House lawyers, according to the memo, directed their colleagues to “lock down” the official word-for-word transcript of that call.

The second issue involves the role the White House lawyers played in delaying the whistleblower’s complaint to Congress. Trump ultimately did not assert executive privilege over the document. But the roundabout way that decision was made and the length of time it took for the declassified complaint to make its way up to Capitol Hill — finally arriving for lawmakers to review in a secure room on Wednesday — have also become a fundamental facet of the Democratic-led inquiry.

Third, and potentially most vexing to Trump’s ability to defend himself should the House impeachment inquiry transition into a full-blown floor debate and then a Senate trial, is the wider role Cipollone and his team will even be able to play in the matter. The White House counsel’s office had an integral role in defending Clinton in his 1998-99 impeachment. But the players in that effort also weren’t witnesses themselves in the alleged misconduct.

On Capitol Hill, where the Trump impeachment inquiry has overtaken pretty much anything else of substance, even a handful of Republicans took issue on Thursday with the way the White House had appeared to handle the Ukraine matter.

“There is a lot in the whistleblower complaint that is concerning,” Rep. Will Hurd, a retiring Texas Republican who sits on the House Intelligence Committee, wrote on Twitter.

Sen. Mazie Hirono, a Hawaii Democrat and ranking member of the Senate Judiciary Committee subpanel that deals with constitutional issues, added: “I don’t know the names of all the players, but clearly the White House is interested in making as sure as possible that this, all of this, wouldn’t see the light of day but for the whistleblower.”

Formal calls for Cipollone’s testimony on Capitol Hill still have yet to materialize. But he did face a deadline Thursday from three House committees investigating his office to submit all White House records connected to the Ukraine scandal, with a subpoena looming if he doesn’t comply. There had been no movement as of Thursday night on the stand-off, though the chairmen of the panels did take issue with the president’s latest comments about the whistleblower that the still-unidentified person was “almost a spy” who could be punished for treason.

“Threats of violence from the leader of our country have a chilling effect on the entire whistleblower process, with grave consequences for our democracy and national security,” said the chairmen, Reps. Adam Schiff of California, Eliot Engel of New York and Elijah Cummings of Maryland.

Impeachment itself is a new threat to the Trump lawyers — the White House did not respond to requests for comment for this article — though some of the ethical and legal issues they’re facing aren’t new. The president’s first White House counsel, Don McGahn, recused himself and his entire office from having any involvement in special counsel Robert Mueller’s Russia investigation after determining they’d been central to several of the key events in the middle of it, including the firings of national security adviser Michael Flynn and FBI Director James Comey.

McGahn himself is mentioned 529 times in the final Mueller report , and his testimony is at the crux of the case that the president committed multiple acts of obstruction of justice in his attempts to stymie or outright stop the Russia probe. At least two of McGahn’s top aides were also interviewed by the Mueller investigators, and notes taken by his chief of staff, Annie Donaldson, quickly drew the ire of Trump.

In the case of the Ukraine scandal, Trump’s White House isn’t dealing with a special counsel or Justice Department criminal investigation. But the impeachment effort is a very real live-fire exercise, and a showdown over demands for their testimony and any requests for executive privilege could quickly find their way into federal court.

Ty Cobb, a former Trump White House lawyer hired specifically to address the Mueller investigation amid McGahn’s recusal, said he didn’t see a similar situation now.

“I don’t see any facts yet that’d require recusal,” he told POLITICO. “I think the White House counsel can be actively involved in this.”

Still, Cobb conceded that his former colleagues shouldn’t be surprised if Congress came knocking for testimony from one or two people in the counsel’s office.

Trump’s presidency has indeed involved a revolving cast of lawyers — both personal and official attorneys representing the businessman-turned-politician. Among the most recognized is Michael Cohen, the longtime Trump Organization lawyer who is serving a three-year prison sentence for his role in a hush-money scheme during the 2016 presidential campaign involving an adult-film actress that also implicated the president. Then there’s Rudy Giuliani, the former New York mayor and current personal lawyer to the president who has spearheaded a controversial media campaign to expose specious claims about the Biden family’s Ukraine ties that has helped create the impeachment storm engulfing the president.

Inside the Trump White House counsel’s office, Cipollone retained John Eisenberg, McGahn’s No. 2 for national security issues, and also added three new deputies: Kate Comerford Todd, the former head of the U.S. Chamber of Commerce’s litigation arm, for judicial nominations; Patrick Philbin, a former top George W. Bush Justice Department official, to deal with policy matters; and Mike Purpura, an ex-Bush White House attorney, to spearhead a team of about 20 attorneys tasked with challenging many of the Democratic oversight efforts.

With the Ukraine scandal, some legal experts have questioned whether the Cipollone-led White House counsel’s office should be playing such a prominent role in an apparent bid to limit the damage for the president.

“Call me old-fashioned, but I really don’t think this is a proper role for a United States government lawyer,” George Conway, a conservative attorney and frequent Trump critic who is married to White House adviser Kellyanne Conway, wrote earlier this week on Twitter.

Philip Allen Lacovara, a former Watergate prosecutor, recalled how multiple Nixon White House lawyers lost their jobs and went to prison for misusing their government positions to protect the president against political embarrassment.

“The White House counsel is a government employee whose professional responsibility is owed to the office of the presidency, not to the personal political fortunes of a particular incumbent,” Lacovara said.

In Trump’s case, Lacovara noted that White House officials had confirmed in the newly disclosed whistleblower complaint that the transcripts of the call between the U.S. and Ukrainian presidents were put on “lock down” for political reasons instead of national security ones.

“Accordingly, it was improper for the White House counsel’s office to participate in the scheme,” he said. “There is a real prospect of legal jeopardy.”

But others have thrown out a yellow flag not to jump to conclusions about whether the White House lawyers themselves will be in any trouble — at least not until more facts are known.

“They have no jeopardy if they did nothing improper, and I haven’t seen any suggestion that they did so,” Jack Quinn, the former Clinton White House counsel, said in an email.

He added: “We’re only at the beginning of this, of course.”

Quint Forgey contributed to this report.