Meet the little-known lawyer behind Democrats’ years-long battle with Trump

By Katelyn Polantz, Jeremy Herb and Tierney Sneed, CNN

House Democrats’ historic decision to release former President Donald Trump’s tax returns this week is the culmination of a nearly four-year legal battle orchestrated by a little-known government lawyer who rewrote the playbook for congressional investigations.

Outgoing House General Counsel Douglas Letter, a 69-year-old government lawyer with a long prior career defending the executive branch, quarterbacked the House’s aggressive litigation strategy, using the courts to fundamentally change the way Congress wields its power — just in time for Republicans to take control of the House next week.

Since 2019, Letter has squared off in court more than a dozen times against Trump, his top advisers and his administration, ultimately suing for access to Trump’s financial information, sensitive administration documents and testimony from some of his closest advisers.

It was an unprecedented gamble. Had Letter lost, Congress’ oversight powers would have been dealt a generational setback by the courts — a perennial fear of lawmakers and lawyers from both parties. Though Letter had the backing of House Speaker Nancy Pelosi, current and former Democratic aides said that he often butted heads with some House Democrats, who were frustrated by the slow-moving courts and cases that outlasted the Trump administration.

“There were some very tense conversations,” one senior Democratic aide told CNN. “We felt like this very powerful oversight tool, if we lost, was gutted.”

Eventually, Letter’s big bet on the court system paid off. House Democrats secured testimony from former White House counsel Don McGahn, brought about the criminal conviction of witness Steve Bannon for contempt, convinced a federal judge to agree Trump may have committed a crime after the 2020 election, obtained Trump-related accounting records, and, after a determination from the Supreme Court last month, finally got their hands on Trump’s tax returns.

In doing so, Letter enshrined key congressional oversight powers, bolstering Congress’ ability to pursue information and dismantling sweeping arguments aimed at shielding Trump from congressional scrutiny.

His victories, however, are bittersweet for Democrats. Come January, those newly won powers will be in the hands of a Republican House majority, which has promised to launch a series of aggressive investigations into the Biden administration. Thanks to Letter’s legal wins, GOP subpoenas will come with more enforcement power, potentially aiding them in future fights to compel testimony from administration officials or even President Joe Biden’s son, Hunter Biden.

“I’m sure that there will be an instance during the time that Republicans control the House that they will benefit from the work that Letter has done in the last four years,” said Tom Spulak, who served as House general counsel under Democratic leadership in 1994 and 1995.

‘Not a TV lawyer’

House Ways and Means Chairman Richard Neal lauded Letter’s role at a news conference last week following his committee’s vote to make Trump’s tax returns public. The Massachusetts Democrat said he talked to Letter nearly every week for the three-plus years the case was ongoing, while heeding the House counsel’s advice not to talk about Trump’s returns on cable TV or to fundraise off the case.

The approach kept the tax returns case on the backburner for years, while the House took other, more challenging cases seeking similar information through the courts.

“Not being an attorney, I scrupulously followed the advice of Doug Letter — who by the way, was not a TV lawyer. He’s argued four times in front of the Supreme Court, and he’s the one that counseled me repeatedly,” Neal said. “At one point I called him in Italy to get an update while he was on vacation. That’s how assiduously we pursued the merits of the case.”

Letter, typically bursting with energy on days he argued cases in court, leaves his position January 3 with the end of the current Congress and will take a new job with Brady, the gun violence prevention nonprofit.

House Democrats’ choice of Letter in late 2018 as their top lawyer immediately stood out. One, because he came to the House from the Justice Department, which would be lawmakers’ opponent in many of the Trump-era disputes. Secondly, because he was a top litigator, a sign the House wouldn’t be afraid of going to court.

Before 2019, it was very unusual for the House to sue — and a risk. The executive branch over decades had found ways to expand and support presidential powers, yet prior House general counsels had typically avoided testing congressional power with judges, especially in appeals that could set precedent. The conventional wisdom was that if tested, the courts could cut back Congress’ power.

Instead, Congress and the executive branch mostly stuck to negotiations over subpoenas, which is formally known as the “accommodations process,” the historical norm.

The calculus for Congress shifted dramatically once Democrats took over the House in 2019 and Trump made clear he would stonewall the chamber’s subpoenas and sue lawmakers if needed.

In practice, that also meant Letter was involved in every step of the process of investigations, according to aides, reviewing language in letters sent to witnesses, news releases that committees issued, and what committee chairs said about the subpoenas publicly. The committees’ actions — including providing extra “accommodations” that Democrats were sometimes frustrated by — were all taken with an eye toward future litigation.

“Doug’s function is to make sure that the only subpoenas that get issued are ones we are prepared to defend in court,” said a senior Democratic aide. “It became clear very quickly we were going to have to defend a lot of subpoenas in court, and so it was his job a lot of the time to say no.”

Among the most difficult decisions for Democratic oversight was the one to pursue Trump’s tax returns. Neal’s hope of trying to find common ground with Republicans on potentially bipartisan issues like infrastructure and tax reform was at odds with the pressure he was feeling from the left to go after Trump’s tax returns. He chose to seek them in April 2019.

The IRS rejected the request — which came after Trump, as a presidential candidate, broke political norms by refusing to release his returns voluntarily — and the House filed a lawsuit to obtain them, starting the long and winding legal road that concluded last month, nearly two years after Trump left office and just weeks before Democrats are set to lose control of the House.

The pace of the court process was frustrating at times for Democrats. “We can’t go out there and say Doug is holding up this process,” said one aide familiar with the discussions. “I think there was little bit of not understanding the political realities that members have and the pressures they get from the public. But that wasn’t his job.”

Letter declined to speak to CNN for this story.

Pushing back on sweeping Trump legal arguments

An early, striking indication of Letter’s willingness to go to court came with the House decision to sue over McGahn not appearing for testimony before the Judiciary Committee, after the Mueller report made clear that McGahn was a central witness to Trump trying to stop the Russia investigation.

“There was a sense of, ‘this is the last bastion of democracy,'” said a former Justice Department official and close observer of the House’s work during Letter’s tenure.

While McGahn had spoken at length to special counsel Robert Mueller for his criminal obstruction investigation, the House took McGahn and the Trump administration through multiple rounds in court before securing his testimony in a settlement after Biden took office. The litigation, where Letter personally argued several rounds, left a trail of mixed results for the House.

The House went on to try a different approach to enforce its subpoenas, looking to federal criminal prosecutors rather than lawsuits for enforcement help.

The select committee investigating the January 6, 2021, attack on the US Capitol made several criminal contempt referrals to the Justice Department when witnesses refused to turn over documents or show up for testimony. Of four recalcitrant witnesses, DOJ declined to prosecute two who served close to the former president but charged Trump advisers Bannon and Peter Navarro criminally.

Bannon was convicted at trial, sentenced to four months in jail, and is appealing — a consequential outcome that may sway other private citizens to try harder to accommodate congressional requests. Navarro heads to trial in January.

Letter also argued a case before the Supreme Court in 2020 where Trump tried to block a House subpoena for his financial information from the accounting firm Mazars USA.

Colleagues of Letter worried that the argument went badly for Congress, yet the House ultimately won the case, albeit with a twist: The Supreme Court said Congress could subpoena information about Trump, but also laid out a specific test lawmakers had to meet to do so.

The battles over the reach of presidential secrecy continued after he left office, with the House prevailing over a Trump bid to block the January 6 committee from obtaining his presidential records from the National Archives.

The House also convinced a trial-level judge to give it access to emails from John Eastman, a Trump elections attorney. In doing so, the judge agreed with House accusations that Trump and Eastman had taken part in the planning of a crime. The House’s legal arguments were some of the boldest a congressional body has ever made in court and laid the foundation for the January 6 panel’s unprecedented criminal referrals of Trump. When the House committee released its final report last week, it recommended changing the law so the House could sue to enforce subpoenas — a weakness Letter’s years of work in court had made apparent.

“This period will be remembered as one of the most significant in history, not just because of the unprecedented obstruction by the Trump administration but because the House committees were able to challenge that,” said Dave Rapallo, the longtime Democratic staff director on the House Oversight Committee who is now a law professor at Georgetown University.

Republicans can build on House Democrats’ gains

Republicans set to take control of House committees said they plan on launching numerous investigations into Biden’s administration as well as his family. Many of those probes may benefit from the court decisions Letter won for congressional investigators.

GOP Rep. James Comer of Kentucky, who’s slated to take over the House Oversight Committee, criticized the Democrats’ aggressive subpoena approach in a recent interview with CNN’s Pamela Brown. Comer has made clear he plans to investigate Biden, questioning the extent he was involved in his son Hunter Biden’s business dealings, but said he didn’t plan to subpoena the president because of the complications.

“The Democrats sent out subpoenas like junk mail, and that’s why it’s hard to get people to come in,” Comer said. “I will be disciplined with subpoenas.”

Others predicted Republicans will be more aggressive than Comer lets on.

“The Republican Congress is going to use every tactic and precedent set by the January 6 Committee,” said Robert Driscoll, a defense attorney in Washington who recently sued the House to block a subpoena.

Republicans’ choice for general counsel will signal what role they see the courts playing in their oversight work while in the majority.

House Minority Leader Kevin McCarthy, who’s fighting for the votes to become speaker in January, is still considering possible candidates for the job, according to a source close to congressional investigations, but that lawyer and their strategy likely won’t be secured until the speakership is settled.

Save for the election of the speaker himself, the source argued, the general counsel selection will be the most consequential choice for the new GOP conference.

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