"You definitely have a corruption problem," he told one at a 2011 legal conference.
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So, as eyes turn to Trump's federal trials, Americans are learning more about Smith's style of "psyching out adversaries."
While he may have "lost some high-profile battles," Smith has been undeterred as he took on Senators, a governor – and even a Staten Island clown.
"He’s saddled, fairly or unfairly, with the stigma of not being able to win the big ones. Yet there’s a feeling among his confidants, some of whom reflected on him as long as their names were kept out, that what matters to him isn’t just the final outcome but the message it sends to would-be wrongdoers, that someone is watching," said the report.
The report said that what Smith might see in Trump is more than an everyday criminal who broke the law.
He "sought to interfere with the peaceful transfer of power by overturning the 2020 election results, and who endangered the nation by sloppily hoarding secret papers and other documents that belong in the National Archives or secure government facilities," the piece continued. "He sees a man who knew full well that he was committing those crimes."
A key piece of the Trump case is interpreting his intent. "And intent is a concept Smith has internalized; he has called it his 'battleground.'"
"On that field of combat, Smith is faced with an adversary whose mastery of shaping public opinion and skewering opponents might be unrivaled. This caustic joker with messianic political appeal has labeled Smith a 'rabid wolf,' 'deranged,' a 'psycho,'" the Post said.
The piece goes on to list a number of strange ways that Smith and Trump's paths have already crossed.
Former Rep. Rick Renzi (R-AZ) was convicted by Smith for "extortion, bribery, insurance fraud, money laundering, and racketeering." Trump pardoned Renzi on his final day in office.
"The same day Trump was pardoning Renzi, boxes of documents were being removed from the White House at the president’s behest to be sent to Mar-a-Lago," said the Post. "No one knew it at the time, but the stage had just been set for the showdown between Jack Smith and Donald Trump."
In another incident, Smith may have saved Trump from a huge international blunder. The ex-president was hosting Kosovo's President Hashim Thaçi in a summit. Smith has become a specialist in investigating Kosovo war crimes while at the International Criminal Court.
While Thaçi was flying to the U.S., Smith dropped his indictment "on war crimes charges dating back to his time as a commander in the Kosovo Liberation Army." Thaçi turned the plane around.
"Smith said the indictment — which normally would have been kept under seal for months — had to be released, because Thaçi was trying to evade justice by secretly working to overturn the law that created the Kosovo war crimes prosecution office," said the report.
Realistically, it saved Trump from a photo-op with a war criminal. Trump has bragged that Thaçi is a "Trump positive person" and his indictment was proof of Smith's long-standing obsession to bring him down.
Trump's logic is that Smith's long history at The Hague prosecuting Kosovo war criminals shows he was lying in wait for Trump to become president and then strike out to get him through a photo-op. Then, years later, he anticipated Trump would try to overthrow the election and he would ultimately be appointed a special counsel.
The piece closed with the cable news obsession with Smith sightings, recalling CNN's "exclusive footage" of Smith buying a Subway sandwich. While the cameras followed his every move from the door to the car, Smith said nothing.
Read the full profile at the Washington Post.
