'Cases up the wazoo for years to come': Legal insiders brace for a world where Trump loses in November and the ex-president faces down a slew of reinvigorated court fights

  • More than a dozen legal experts and practitioners tell Insider that Donald Trump's many legal fights are primed to cause him headaches should he lose the 2020 presidential election.
  • There are lawsuits tied to whether the president violated the US Constitution forbidding him from making money off foreign governments, possible Hatch Act violations, Trump's business entanglements, and campaign finance questions still stewing from the Stormy Daniels hush money affair. 
  • Trump's 2020 campaign also faces accusations its masking the true recipients of about $170 million in election season spending.
  • The existence of an internal Trump campaign audit of spending irregularities may also entice federal investigators. A Trump official says the campaign 'complies with all campaign finance laws.'
  • Could the Mueller investigation make a comeback? Possible, former Justice Department and Federal Election Commission officials say. 
  • Visit Business Insider's homepage for more stories.

The scenario: It's January 20, 2021. 

Joe Biden is now president of the United States, having denied President Donald Trump his bid for a second term. Trump vacates the White House and retreats to his Mar-a-Lago resort in Florida. For Trump's political career, it's all over but the tweeting.

Or is it?

More than a dozen legal experts and practitioners, including former high-ranking officials at the Department of Justice and Federal Election Commission, tell Insider that legal troubles for Trump and a vanquished Trump reelection campaign could ignite — not subside — if the president is no longer president.  

Department of Justice officials may already be discreetly probing Trump reelection activity, according to several of the legal experts. 

Of particular interest, potentially: accusations that the Trump campaign is masking the true recipients of about $170 million in election season spending. The existence of an internal Trump campaign audit of spending irregularities may also entice federal investigators, they said.

New criminal inquiries into Trump campaign activity, if pursued, would further deepen an already extraordinarily wide-ranging legal mess facing a post-presidency Trump. 

The list is long, and it covers a bunch of topics that contribute to an increasingly intricate tapestry of ongoing Trump trouble. It include lawsuits tied to an obscure section of the US Constitution forbidding a president from making money off foreign governments, possible Hatch Act violations, the president's business entanglements, lingering Mueller investigation matters, and campaign finance questions still stewing from the Stormy Daniels hush money affair. 

"Trump, in some form or another, will have cases up the wazoo for years to come," said Joshua Geltzer, a former Justice Department and National Security Council attorney.

The Trump campaign did not respond to Insider's questions this week about the possible legal challenges ahead for the president and his team. In July, Trump 2020 Communications Director Tim Murtaugh said the campaign "complies with all campaign finance laws and FEC regulations."

Justice Department investigation 'plausible'

Could Trump's own Justice Department, at this moment, be criminally investigating the Trump reelection campaign?

"Plausible," said Geltzer, who is now the executive director of the Institute for Constitutional Advocacy and Protection at the Georgetown University Law Center.

"Possible — very," added Ann Ravel, a former Federal Election Commission chairperson and deputy assistant attorney general during the Obama administration.

If so — and that's a big "if" — the public almost certainly wouldn't know until after Election Day on November 3, said Daniel Petalas, a former FEC acting general counsel and trial attorney in the Justice Department's public integrity section.

That's because DOJ operates under a directive to not inadvertently influence elections immediately before one takes place. And that means officials there would "likely be avoiding public investigative steps" even if they were examining Trump campaign activity, said Petalas, now a partner with law firm Duggins Wren Mann & Romero LLP.

Sensitivities surrounding such a matter are pitched. For that, thank the much-maligned actions four years ago of then-FBI Director James Comey and the Justice Department while investigating then-Democratic presidential nominee Hillary Clinton's use of a private email server while conducting business as secretary of state.

The Justice Department, which did not respond to a request for comment, has meanwhile maintained since the Watergate scandal in the early 1970s that a sitting president cannot be indicted for any reason, campaign-related or otherwise.

Trump family involvement?

At the core of the Trump campaign's current money drama is whether the Trump campaign "disguised" nearly $170 million worth of campaign spending "by laundering the funds" through companies led by the former campaign manager Brad Parscale or created by Trump campaign lawyers, according to a complaint filed this summer with the FEC by the nonpartisan Campaign Legal Center. The FEC is the civil enforcer and regulator of campaign finance laws, but it will work alongside the Justice Department if a political committee or actor is suspected of criminally violating election laws.

The complaint further contends that the Trump campaign's spending practices have the practical effect of masking payments — in violation of federal campaign-transparency rules — to various advertising contractors and senior Trump campaign staff and family members. 

Among them: Lara Trump, the wife of the president's son Eric Trump, and Kimberly Guilfoyle, the girlfriend of Donald Trump Jr. whose larger-than-life appearance at the Republican National Convention instantly boosted her profile.

Separately, Insider on July 17 reported that the Trump campaign is conducting an internal review of campaign spending irregularities overseen by Parscale.

There's a "distinct possibility" that the Justice Department, in addition to the FEC, would show interest in the Trump campaign's financial dealings, said Adav Noti, the Campaign Legal Center's chief of staff and senior director of trial litigation. 

But Noti agreed that any definitive, public Justice Department action, were any to happen, won't likely occur until next year once the 2020 presidential campaign is history.  

Headwinds ahead

For Democrats and other Trump detractors who want the president to pay for what they believe are campaign crimes, there are several significant obstacles.

Foremost, campaign finance cases are difficult to prosecute.

Yes, there are a few slam-dunk convictions, such as when former Rep. William Jefferson, a bribed-up Louisiana Democrat, got caught with a stack of illegal cash in his freezer, or when former Rep. Jesse Jackson Jr., an Illinois Democrat, raided his campaign kitty to pay for vacations and luxury goods.

But the Justice Department's salacious 2012 case against John Edwards, which alleged the former 2008 Democratic presidential candidate used almost $1 million in political donor cash to hide a sexual affair with his campaign videographer, crashed and burned. That failure remains fresh for federal officials, attorneys interviewed said.

Moreover, if members of a political candidate's campaign staff is engaged in criminal wrongdoing, tying such allegation to the candidate himself is "tough to pursue because they require knowledge and willfulness," said Luke Cass, a former senior trial attorney in the Justice Department's public integrity section who now leads the white collar and internal investigation practice at law firm Quarles & Brady LLP.

There's also the problem of the FEC, chief investigator of campaign finance misdeeds, being rendered all but powerless because it lacks commissioners. It needs at least four for a quorum but has had only three for most of the past year. 

The Justice Department doesn't need the FEC to act on its own. And there's ample thirst for reciprocal vengeance among some Democrats who've endured Trump's "lock her up!" taunts of Clinton. 

Nevertheless, the Justice Department under a hypothetical Biden administration might also consider forgoing prosecutorial action against Trump or his associates in the spirit of moving past Trump's White House tenure. 

Besides, said Alan Dershowitz, who represented Trump during his impeachment trial, Biden-era Justice Department actions against Trump "would be very, very easy to defeat. It would be seen by the public as extremely political."

Still, if Trump lost reelection and felt threatened by potential legal action against him he'd retain the power to pardon or commute the sentences of people close to him until Biden's inauguration. That's not altogether out of the realm of the possible given the actions he's taken on several occasions during his presidency, most recently with Stone, his longtime political adviser. 

At the fringes of constitutional law looms a scenario where Trump attempts to pardon himself. Or, in an even more legally exotic move, Trump resigns the presidency before leaving office on January 20 and arranges for then-President Mike Pence to grant him and his associates a blanket pardon. 

Such a scenario has never happened before, though a top Justice Department official back on the eve of Richard Nixon's resignation in August 1974 did weigh its legality.

Dershowitz, for one, says such discussions for Trump are nonsense.

"Zero chance of it happening," he said.

Jerry Goldfeder, a New York election law lawyer who's represented numerous Democrats during a 40-year career, said it "would be shocking for the president to use his pardon power to protect himself and close campaign associates." But, he added, "it wouldn't be surprising." 


Former Special Counsel Robert Mueller arrives to testify before Congress on July 24, 2019, in Washington, D.C.AFP/Saul Loeb via Getty Images

'This isn't going away'

Beyond 2020 campaign activity, Trump already faces a swamp's worth of other legal sinkholes.

There's the ongoing emoluments lawsuit involving his Washington, D.C., hotel and repeated apparent violations of the federal Hatch Act by White House officials. The outcome of a criminal campaign finance-related investigation involving Trump lawyer Rudy Giuliani remains under wraps, though several associates of the former New York mayor are scheduled to go on trial in February 2021 in federal court in Manhattan.

At the FEC, a complaint remains pending from Democratic Rep. Bill Pascrell of New Jersey involving disputed Trump campaign police bill debt. Potential federal campaign fines, stemming from thousands of pages worth of Trump campaign finance contributions the FEC has already flagged throughout the 2020 campaign as "excessive" or "impermissible," also loom.

In 2018, Trump chided President Barack Obama because Obama's campaign committed "a big campaign finance violation." 

Indeed, the FEC in 2013 slapped Obama's 2008 presidential campaign with a $375,000 penalty for not properly disclosing the contributions of hundreds of big-dollar donors. More recently, in 2019, the FEC hit a pro-Jeb Bush super PAC and Chinese-owned company supporting it during the 2016 presidential campaign with $940,000 in total fines.

But several former Justice Department and FEC attorneys suggested Trump's greatest post-presidency legal peril may come from one of two other realms. 

One is the reemergence of Special Counsel Robert Mueller's report on foreign infiltration in 2016, which included an entire section outlining at least 10 instances where the president may have obstructed justice.

"Mueller laid the groundwork for criminal offenses," Ravel said. "If I was President Trump, that's what I would be worried about."

The other is a state-level investigation, led by New York Attorney General Letitia James, into Trump's company, the Trump Organization.  

Norm Eisen, a former Obama-era White House special counsel for ethics, said in an interview that if he were Trump and had just lost reelection in November, "my preeminent concern would be to have a good attorney to negotiate a plea bargain.

"We've never seen such an unethical, dishonest, corrupt administration, and there are substantial questions about the lack of transparency and candor of the Trump campaign and those around it," said Eisen, who also served as counsel for Democrats on the House Judiciary Committee during Trump's impeachment. "This isn't going away."

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