On Aug. 17, Rudy Giuliani stepped out of a black SUV outside the Fulton County Courthouse in Atlanta and pushed his way through a mass of reporters shouting the same question: What did he plan to tell a grand jury about his efforts to sabotage the 2020 election results on behalf of Donald Trump? Would he take the Fifth? “They ask the questions and we’ll see,” he said. When he made it to the front door it was locked — he’d arrived before business hours. For 30 awkward seconds, he was cornered, laughing nervously as he waited for someone to open the door.
For anyone who has followed his long career, Giuliani’s courthouse appearance was a riveting spectacle. For much of the 1980s and ’90s, the prosecutor-turned-mayor swept into government buildings like this with an almost cinematic boldness, the most feared man in town heading into the next big battle with his entourage of dark-suited aides and plainclothes detectives. Now he is a diminished figure, angling to persuade jurors and prosecutors to keep him off the path to prison. Even if he escapes indictment in Georgia, there are two Justice Department inquiries he must survive.
It is a moment of reckoning for a man whose gleeful flirtation with danger over the decades has led him to this crucible. Perhaps none of his troubles would have emerged if he had never met Trump. Or maybe his character flaws made them inevitable.
From the start of his career, Giuliani thrived on risk-taking, the more dangerous the better. His lifelong best friend, Peter Powers, who died in 2016, liked to say that the former mayor was born without a “fear gene.” His audacity often served the public well: He was fearless in prosecuting mobsters as a U.S. attorney; fearless in fighting special interests as a New York mayor; fearless in leading the city after a terrorist attack.
But fearlessness has a flip side, and that is recklessness. Where fearlessness propelled Giuliani to his biggest accomplishments, recklessness loosed his destructive impulses.
His mayoral years were a dizzying tableau of heroism and heedlessness. To the city’s civil liberties and homeless advocacy groups, Giuliani’s order upon taking office in 1994 that police rid the streets of vagrants urinating or sleeping on sidewalks and in the subways was considered almost heresy. So grateful was the public, though, for the restoration of sanity in their neighborhoods that by the end of his first term, few, if any, elected Democrats would dare vow to undo his policies.
But Giuliani’s obsession with control led to a series of wildly reckless acts. He grew to resent the credit the media was giving to William Bratton, his hugely effective police commissioner, and forced him out in 1996. He then turned up the pressure on Bratton’s successors to reduce crime further, triggering a wave of police harassment of young men in Black neighborhoods. When innocent people from those communities were killed by the police, Giuliani refused to acknowledge the problem or even meet with the city’s Black elected officials. “Maybe it isn’t an altar boy,” he famously remarked of Patrick Dorismond, killed outside a Midtown bar by officers who mistook him for a drug dealer.
Three months after Bratton’s resignation, TWA Flight 800 exploded and crashed off the coast of Long Island after taking off from JFK airport, killing all 230 people on board. Giuliani raced to the side of terrified relatives and unleashed his fury at TWA — including its chairman — for its meager efforts to get information to them. He made it a virtual crusade against the airline, which buckled to his demands. He was widely lauded for standing up for his citizens.
The same man was cheating on his wife, carrying on at least one extramarital affair while married to Donna Hanover, who was still living in the mayoral mansion. When the city’s tabloids uncovered the relationship in 2000, the revelation blew up into a scandal that tainted his reputation for decades.
For anyone who has followed his long career, Giuliani’s courthouse appearance was a riveting spectacle. For much of the 1980s and ’90s, the prosecutor-turned-mayor swept into government buildings like this with an almost cinematic boldness, the most feared man in town heading into the next big battle with his entourage of dark-suited aides and plainclothes detectives. Now he is a diminished figure, angling to persuade jurors and prosecutors to keep him off the path to prison. Even if he escapes indictment in Georgia, there are two Justice Department inquiries he must survive.
It is a moment of reckoning for a man whose gleeful flirtation with danger over the decades has led him to this crucible. Perhaps none of his troubles would have emerged if he had never met Trump. Or maybe his character flaws made them inevitable.
From the start of his career, Giuliani thrived on risk-taking, the more dangerous the better. His lifelong best friend, Peter Powers, who died in 2016, liked to say that the former mayor was born without a “fear gene.” His audacity often served the public well: He was fearless in prosecuting mobsters as a U.S. attorney; fearless in fighting special interests as a New York mayor; fearless in leading the city after a terrorist attack.
But fearlessness has a flip side, and that is recklessness. Where fearlessness propelled Giuliani to his biggest accomplishments, recklessness loosed his destructive impulses.
His mayoral years were a dizzying tableau of heroism and heedlessness. To the city’s civil liberties and homeless advocacy groups, Giuliani’s order upon taking office in 1994 that police rid the streets of vagrants urinating or sleeping on sidewalks and in the subways was considered almost heresy. So grateful was the public, though, for the restoration of sanity in their neighborhoods that by the end of his first term, few, if any, elected Democrats would dare vow to undo his policies.
But Giuliani’s obsession with control led to a series of wildly reckless acts. He grew to resent the credit the media was giving to William Bratton, his hugely effective police commissioner, and forced him out in 1996. He then turned up the pressure on Bratton’s successors to reduce crime further, triggering a wave of police harassment of young men in Black neighborhoods. When innocent people from those communities were killed by the police, Giuliani refused to acknowledge the problem or even meet with the city’s Black elected officials. “Maybe it isn’t an altar boy,” he famously remarked of Patrick Dorismond, killed outside a Midtown bar by officers who mistook him for a drug dealer.
Three months after Bratton’s resignation, TWA Flight 800 exploded and crashed off the coast of Long Island after taking off from JFK airport, killing all 230 people on board. Giuliani raced to the side of terrified relatives and unleashed his fury at TWA — including its chairman — for its meager efforts to get information to them. He made it a virtual crusade against the airline, which buckled to his demands. He was widely lauded for standing up for his citizens.
The same man was cheating on his wife, carrying on at least one extramarital affair while married to Donna Hanover, who was still living in the mayoral mansion. When the city’s tabloids uncovered the relationship in 2000, the revelation blew up into a scandal that tainted his reputation for decades.
