Former FBI Director James Comey wasn’t always atop President Donald Trump’s enemies list.

“You’ve had one heck of a year,” Trump, then the president-elect, said to Comey in January 2017, the first time they met face-to-face privately at Trump Tower in New York. Trump told Comey he had a “great reputation” and handled the FBI’s investigation into Hillary Clinton’s use of a private email server “honorably,” according to Comey’s re-telling of their meeting in his 2018 memoir.

That might have been the high point of their relationship.

Moments later, the FBI director told Trump for the first time about the infamous “Steele dossier,” which alleged that Trump and his campaign colluded with the Russians to win the 2016 election. It was a conversation that would ultimately send Comey spiraling down the path to becoming one of Trump’s chief villains.

Now, Comey is caught in the middle of Trump’s second-term retribution campaign, after he was charged last month with a two-count criminal indictment for allegedly lying to Congress in 2020 about leaks, which CNN has reported appears to be related to the FBI’s Clinton email investigation.

Comey, who has said he is “innocent” of the charges, is set to be arraigned at an Alexandria, Virginia, federal courthouse Wednesday morning.

Along the way, unlike his recent FBI predecessors, Comey forged an unprecedented decade-long path to becoming a major political actor, whose every action is weaponized by partisans from both sides for their own gain. He went from a Democratic scapegoat for the party’s 2016 election loss, to a catalyst for the appointment of special counsel Robert Mueller, to a prominent anti-Trump resistance figure, and now, a criminal defendant.

“Trump is the ultimate pugilist and Comey is his punching bag, because Comey pricks away at Trump’s ego and paranoia,” said Douglas Brinkley, CNN Presidential Historian and a history professor at Rice University. “History will look at them both with jaded eyes, over the fact that these two grown-ups put their country through so many nauseating news cycles of schoolyard one-upmanship.”

Here are the key moments that define the long and winding Trump-Comey grudge:

Clinton bombshells roil 2016

Many Americans had probably never heard of Jim Comey before July 5, 2016.

That’s when – in the heat of a presidential campaign, with the party conventions just weeks away – Comey held an unprecedented 15-minute press conference explaining the results of the FBI’s yearlong investigation into Hillary Clinton’s email server.

Comey blasted Clinton for being “extre