Jack Smith Is Known to Take On Tough Cases. But He Doesn’t Always Win.

Jack Smith, the special counsel who brought historic, back-to-back indictments of a former president, has developed a reputation as an aggressive prosecutor known for trying high-stakes, politically explosive cases. 

But he hasn’t always prevailed.

Smith led the Justice Department’s public corruption unit more than a decade ago, when it brought several cases against lawmakers and politicians that legal experts say were based on far-reaching interpretations of federal law that sometimes backfired before juries and courts.

Now he faces the most consequential case of his extensive career, the prosecution of Donald Trump on charges that he conspired to undo his 2020 election loss. In doing so, Smith is relying on theories that present legal questions that some experts say could go either way in court. 

Smith and some of his prosecutors were present Thursday when Trump pleaded not guilty to four crimes, including conspiring to defraud the U.S., obstructing an official proceeding and conspiring against the rights of voters. A lawyer who worked with Smith called it a “classic Jack case”—streamlined, compelling and easy to follow.

While some defense attorneys viewed the indictment as strong and straightforward, others said the case pushes the envelope.

“This case is clearly on the frontier of American jurisprudence: using general and broad conspiracy and fraud theories to convict a politician for transgressions against the state,” said Stan Brand, a defense lawyer who has represented several Trump associates. 

Some former prosecutors said the indictment doesn’t clearly define which specific moments Trump’s actions became criminal. It notes, for example, that it isn’t a crime to falsely claim he won an election, but that Trump also “pursued unlawful means of discounting legitimate votes and subverting the election results.” Where the line stands between the former and the latter isn’t clearly spelled out in the indictment, some former prosecutors said.

Other experts say if the theories are novel, it is because so are the facts: Never before has a defeated president been accused of trying to block the peaceful transfer of power to his successor.

Trump has denied wrongdoing and accused Smith—whom he has personally attacked as “deranged”—of pursuing him to undermine his candidacy in the 2024 Republican presidential nomination. 

The latest indictment follows separate charges Smith brought in June alleging Trump retained classified documents after he left the White House and tried to obstruct their recovery, the first-ever federal criminal case against a former president. Trump has pleaded not guilty to those charges. 

Smith, a registered independent, brings to the Trump cases a wide-ranging prosecutorial career on the local, national and international levels. He has handled a range of complex investigations that involved some of the most serious offenses committed by government officials, including corruption and war crimes. 

Attorney General Merrick Garland

After Tuesday’s indictment, Garland praised Smith and his team as “experienced and principled, agents and prosecutors” and said they have “followed the facts and the law wherever they lead.”

A spokesman for Smith declined to comment.

Trump’s supporters have attacked him as partisan, even though he pursued both Republicans and Democrats.

Smith took over the Public Integrity Section in 2010, as it was reeling from the implosion of its case against the late Republican Sen. Ted Stevens after prosecutors failed to turn over evidence that would have helped the defense. Shortly after his arrival, Smith reviewed some long-running investigations into members of Congress and recommended closing several of them without charges. But the section’s court work began to pick up, as he worked to improve the team’s trial skills. The section tried 17 cases in 2011, and 12 the next year.

Alongside successes were some setbacks. Prosecutors charged former Democratic Sen. John Edwards

At trial, the jury deadlocked on most of the charges and acquitted Edwards on one charge. 

​​“I felt like the evidence just wasn’t there. It could have been more,” a juror told reporters at the time. The Justice Department dropped the case in 2012. 

The same year, a jury for a second time acquitted a casino owner and several state lawmakers in a prosecution brought by Smith’s unit alleging the lawmakers were being bribed to legalize gambling in the state. The case centered on whether the conduct was criminal or just a seamy part of the legislative process. Jurors found the latter.

In 2014, Smith’s office brought charges against Republican Gov. Bob McDonnell of Virginia. In that case, McDonnell accepted $175,000 worth of loans and gifts from a businessman with interests in front of the state. In an 8-0 decision, the Supreme Court overturned McDonnell’s conviction, saying that prosecutors needed to show an explicit quid pro quo between gifts or donations and official actions to bring certain corruption charges.

Prosecutors had brought the case under an aggressive theory of corruption, which lower courts affirmed. But the high court narrowed the scope of behavior covered by federal law, with Chief Justice John Roberts saying the Justice Department’s theory of the case was so broad it could criminalize ordinary constituent service and other conduct that politicians engage in routinely. 

Smith left the unit in 2015, after his team launched an investigation into Sen. Robert Menendez, (D., N.J), whose federal corruption case ended in a mistrial when jurors deadlocked two years later. 

Lanny Breuer, the former head of the Justice Department’s Criminal Division who hired Smith to run the unit, said the mixed record is more a reflection of the challenges public corruption prosecutors routinely face than of Smith’s approach.

“If you only win your cases, you’re not bringing hard cases,” Breuer said. “It’s very, very difficult to get convictions.”

Under Smith’s leadership, the unit also prevailed in a number of other cases, including that of former Arizona Rep. Rick Renzi, who in 2013, was sentenced to three years in prison after he was found guilty of misusing his office in a fraudulent land deal. There was also Phillip Hamilton, a former Virginia lawmaker who was sentenced to nine-and-a-half years in prison for bribery and extortion. 

Smith’s stint in Public Integrity came after working in the Manhattan district attorney’s office and a nine-year run at the U.S. attorney’s office for the Eastern District of New York. During his tenure, he notched convictions in some of the office’s highest-profile and most complex cases, according to former colleagues. 

In 2002, he was picked to be one of the lead prosecutors in the retrial of a former New York Police Department officer accused of aiding in the torture of Haitian immigrant Abner Louima while in custody in a Brooklyn precinct station house. An appellate court had overturned two previous convictions of the defendant, Charles Schwarz, setting up a heated third trial.

After six days of deliberating, the jury convicted Schwarz of perjury but deadlocked on the more serious civil-rights charges. Prosecutors planned to seek a fourth trial but, in a last-minute agreement, allowed Schwarz to plead guilty to another perjury charge to end the matter. He was sentenced to five years in prison.

Smith’s next big trial was a death-penalty case against Ronell Wilson, a gang member charged with killing two undercover NYPD detectives. A jury convicted Wilson and sentenced him to death. However, a federal appeals court later overturned the death sentence, saying Wilson’s Sixth Amendment right to a fair trial had been violated when Smith told the jury during the penalty phase that they should sentence him to death partly because he had refused to testify or admit his guilt.

Write to Sadie Gurman at [email protected] and James Fanelli at [email protected]