Southern District of New York probes restricted ‘October surprise’ rules

The U.S. Attorney’s Office for the Southern District of New York has a reputation for targeting conservative and Republican political figures, but a review of federal cases by The Washington Times revealed that plenty of Democratic players also feel the sting of the office’s aggressive prosecutions.

The office, which handles some of the highest-profile cases, can’t deny that it has repeatedly tried to put the pinch on President Trump’s entourage.

Over three years, prosecutors oversaw multiple investigations into Mr. Trump’s inner circle. They scored a guilty plea from his longtime fixer Michael Cohen and lodged indictments against two associates of his personal attorney, former New York Mayor Rudolph W. Giuliani, and, separately, former White House adviser Steve Bannon.

Two probes, including one into the business dealings of Mr. Giuliani, are reportedly still active.

Prosecutors have ensnared even minor figures in the Trump orbit. Last year, SDNY attorneys lodged an indictment against Chicago bank executive Stephen Calk, a member of the Trump campaign’s economic advisory team in 2016.

The investigations have rankled Mr. Trump and his supporters, who fume that Democrats aren’t receiving equal scrutiny.

Mike Davis, a former attorney for the Senate Judiciary Committee and founder of the conservative Article III Project, ticked off a litany of Democrats who seemingly got a pass when they faced allegations of wrongdoing.

“With all of these other groups like David Brock’s Media Matters, the Clinton Foundation cash machine, Black Lives Matter and Antifa, it’s just amazing to me that these federal prosecutors only seem to find wrongdoing on the right,” he said.

While those major left-leaning entities haven’t been snared in SDNY’s net, the prosecutors won convictions against at least six Democratic political figures in the past five years.

Those taken down included New York Assembly Speaker ex-Sheldon Silver, who was considered the second most powerful politician in New York behind Gov. Andrew Cuomo, former Rep. Anthony Weiner and anti-Trump celebrity lawyer Michael Avenatti.

Roland Riopelle said the office, where he worked as a prosecutor for several years, has earned a reputation for independence.

“I think that office has a huge commitment to avoiding the appearance of political influence. Sheldon Silver is a good example,” he said. “There is no consideration of what would be the political fallout from any prosecution.”

The office historically has operated almost independently from the Justice Department. That lack of oversight earned it the nickname “the Sovereign District of New York,” a moniker used both derisively and as a badge of honor.

SDNY’s litigation sometimes gets confused amid the barrage of New York legal action aimed at entities and people in the Trump orbit.

New York State Attorney General Letitia James filed a civil lawsuit accusing the National Rifle Association of a slew of financial wrongdoing and seeking its dissolution. In 2016, the gun rights group spent $50 million to elect Mr. Trump and other Republicans.

Manhattan District Attorney Cyrus Vance, also not a federal prosecutor, issued a subpoena seeking financial documents and tax records from Mr. Trump and his real estate business, the Trump Organization. He scored a win last month when the Supreme Court upheld the subpoena’s validity.

Any of the investigations could upend the presidential race or create an October surprise.

However, time is running short on the federal SDNY probes. Under Justice Department regulations, federal prosecutors cannot bring charges against a political candidate or influence “electoral matters” 60 days before an election.

That would give the SDNY about two weeks to pull the trigger on any investigations or wait until after Election Day. Attorney General William P. Barr, a Trump appointee, could override the federal guideline against “October surprise” indictments.

The investigations fall within the jurisdiction of local and federal prosecutors in New York because that is where Mr. Trump has resided and where the Trump Organization has headquarters.

An impressive list of alumni rose through the SDNY’s ranks to have national successes on both sides of the political aisle. Two Supreme Court justices, Felix Frankfurter, a Democratic appointee, and John Marshall Harlan, a Republican appointee, got their start prosecuting cases for the Southern District.

Two political rivals, Mr. Giuliani and former FBI Director James B. Comey, worked together at the SDNY.

Mr. Giuliani hired Mr. Comey, a longtime Republican turned Trump opponent, to join his team of prosecutors in 1987. The two now repeatedly slam each other in cable television appearances.

Conservatives last week bristled when SDNY prosecutors indicted Mr. Bannon on fraud charges. He, along with three others, is accused of defrauding donors who contributed money to build a wall along the southwestern border.

Mr. Bannon pleaded not guilty to the charges.

“The talking point will be that this particular office has been political, but I think there is a difference here because it was conservatives who were allegedly defrauded,” said Matthew Schmidt, who has worked with the Senate and the House Armed Services Committee and now teaches at the University of New Haven.

The SDNY ordinarily has to give the Justice Department advance notice for a high-profile case, such as the indictment of Mr. Bannon, but does not necessarily need permission.

U.S. attorneys’ offices usually do seek approval from the Justice Department before advancing a significant case, although it is not known whether Mr. Barr green-lighted the Bannon case.

“Someone like Steven Bannon would have to be signed off by people in Washington,” Mr. Riopelle said. “They may have signed off on it because they thought it would leak that they didn’t sign off on it. And that would be a worse hit.”

The Bannon prosecution adds to the tension between the Trump administration and the SDNY. Prosecutors filed charges just weeks after Mr. Barr bungled the firing of Geoffrey Berman, then the U.S. attorney for the Southern District of New York.

Mr. Barr in June unexpectedly announced that Mr. Berman would be “stepping down.” But Mr. Berman refused to resign, creating an embarrassing tug of war for the administration. The standoff finally ended when Mr. Trump fired him, but only after his deputy Audrey Strauss was named as acting replacement.

At the time, Democrats clamored that the attorney general wanted Mr. Berman out to halt investigations into Trump associates. Mr. Barr dismissed those claims as “ludicrous,” but Democrats revived the accusation after Mr. Bannon’s arrest.

“This could be the reason former SDNY head Berman was removed from his position by Attorney General Barr last month,” tweeted House Judiciary Committee Chairman Jerrold Nadler, New York Democrat.

In closed-door testimony before the House Judiciary Committee, Mr. Berman said he worried that his firing would delay or disrupt ongoing investigations, but he did not say whether his departure affected any probes.

Republicans said there is no evidence that Mr. Berman’s termination hampered any investigations and noted that they continued under Ms. Strauss.

Eliminating Mr. Berman wouldn’t stop investigations by line prosecutors, Mr. Davis said.

“This notion that firing Berman was to obstruct these investigations is utterly nonsense and evidence-free,” he said. “Anyone who knows anything about how U.S. attorneys offices, especially SDNY, work, would laugh at that conspiracy theory,” he said.

Still, Ms. Strauss is a registered Democrat who has donated to Democratic candidates in the past, making her an easy target for Mr. Trump to claim the prosecutions are political.

“The Trump campaign is going to convince [supporters] the Southern District of New York is part of the deep state,” Mr. Schmidt said. “They don’t know the Southern District of New York. They have never been to the Southern District of New York.”

Mr. Davis said the best course of action would be to let the SDNY prosecutors move forward without political interference.

“Do you need to rein in federal prosecutors who are charging people with crimes? No. That would be wrong as a legal matter and a policy matter, and it would be utterly stupid as a political matter,” he said.

The SDNY in 2018 won a guilty plea from Cohen for campaign finance crimes. SDNY prosecutors also indicted two Giuliani associates tied to the Ukraine investigation that led to Mr. Trump’s impeachment.

Mr. Giuliani has not been charged with a crime, but the SDNY is reportedly investigating his financial dealings with the two indicted associates. It is also looking at corruption accusations against Mr. Trump’s inaugural committee.

Prosecutors also accused Mr. Calk of approving high-risk loans to former Trump campaign chairman Paul Manafort in exchange for a position in the administration, which he did not receive.

On the Democratic side of the ledger, SDNY prosecutors convicted Avenatti on charges related to an attempted shakedown of sportswear maker Nike.

It also secured a 21-month prison sentence for Mr. Weiner, who pleaded guilty to sending obscene photos to an underage girl.

They also convicted Eric Stevenson, a Democratic member of the New York Assembly, of bribery and extortion, New York state Sen. Larry Seabrook, a delegate to the 2004 Democratic National Convention, of money laundering, extortion and fraud; and Spring Valley Deputy Mayor Joseph Desmaret of bribery.

Mr. Silver also was convicted of seven counts of corruption, triggering the longtime speaker’s automatic expulsion from the Assembly.