The Governor and the Darkness

A visual interpretation of the governor’s very bad week by Patrick Thomas, left, and Rodrigo Corral, right.

He loved the black-bag job. Eliot Spitzer was a 30-year-old assistant district attorney in Manhattan charged with investigating mob control of trucking in the garment district when he found joy in the undercover. Spying on the Gambinos was a world away from Riverdale, where he’d grown up the son of a real-estate mogul, and from Princeton and Harvard Law School, where he’d been at the top of his classes. Spitzer’s father had driven all three of his children to push their intellectual limits, but figuring out a way to break into the Gambinos’ West 35th Street office to plant a bug—by using Con Ed trucks on a phony repair call, by picking locks, switching off alarms, and evading motion detectors—then listening to hundreds of hours of tapes of Tommy and Joe Gambino cursing and joking and scheming? That was the life.

It was all in service of a noble cause, of course, like ending the “mob tax” on clothing manufacturers. The Gambinos were clearly evil. So when setting up a sham store on Chrystie Street and a bogus trucking company didn’t produce enough evidence, Spitzer pushed the plot to install a listening device. And when racketeering laws didn’t seem to fit, he found a creative way to use the antitrust statute. The trial was fun, too. But the real thrill was in the cloak-and-dagger. The whole investigation took three years, and every chance he got, he’d slip on the headphones and listen to tapes from the wire. Ever since, Eliot Spitzer has been hooked on the clandestine.

She couldn’t stop crying. Barely one day earlier, the man she’d been married to for two decades, the father of her three daughters, had stunned Silda Wall Spitzer with the revelation that he’d been sleeping with prostitutes. Now here they were, on a cloudy Monday afternoon, in a warren of state-government offices on the 39th floor of a midtown building, among shell-shocked and tearful staffers. The New York Times had just broken the story on its Website.

She hated what he’d done, hated the idea of being seen as a “stand by your man” wife. But maybe appearing together today would somehow help their daughters through this nightmare. And Silda, an experienced lawyer herself, had somehow been able to think objectively about what her absence might say to federal prosecutors. She and Lloyd Constantine, a longtime Spitzer confidant, were nearly alone in arguing against an immediate resignation; Eliot, recognizing he was a political dead man, had wanted to do it first thing Monday morning. So they’d settled on a press conference in which Spitzer would apologize, admit nothing, and cling to his job. It was scheduled to begin at 2:15. Nearly an hour later, Silda wasn’t ready for an excruciating appearance in front of the press.

Spitzer stood still, not trying to console her or to make excuses. He was silent, his head down. He would wait as long as Silda needed. Spitzer dabbed his eyes. Silda slowly composed herself. Then they walked through the door, into the glare of TV lights, for the beginning of the end. Eliot Spitzer’s secret was out.

Sifting for clues in the wreckage of Eliot Spitzer’s stunning, sordid prostitution scandal—and trying to make sense of what no doubt will always contain a large element of pure insanity—that old mob investigation offers a vivid glimpse into the suddenly ex-governor’s psyche. “I don’t think [the prostitutes] were so much about the sex,” says one man who worked closely with Spitzer for many years and thought he knew him well. “There’s definitely an element of self-destruction. There’s complete ‘the rules don’t apply to me’; it’s very arrogant. But Eliot loves covert ops. He always has. The most animated or excited he ever gets is when he talks about running the sting on the Gambino family.”

Plenty of Spitzer targets, particularly in the financial industry, have long complained that he was a hypocrite whose ethical righteousness didn’t apply to his own tactics and behavior. As long as Spitzer was wearing the white hat, though, as long as he appeared to be crusading on behalf of wronged mutual-fund investors or exploited deli workers, much of the public and the media were happy to look the other way. Spitzer’s combative style hit a wall when he arrived in Albany, though, and when he resorted to stealth tactics, trying to embarrass State Senate Majority Leader Joe Bruno over the use of a state helicopter, Bruno proved craftier and less easily intimidated than Spitzer’s Wall Street adversaries. The ironies are obvious and abundant. Covert operations made him, and they destroyed him. Humiliation was his weapon and his punishment. Last week no one even attempted to defend him.

By Rodrigo Corral, left, and Chip Kidd, right.

How well did Eliot Spitzer know himself? When Spitzer announced his run for governor, he realized he had to soften his prosecutorial image a bit. So in November 2005, Spitzer was one of the first guests on The Colbert Report. When the talk turned to Spitzer’s childhood soccer career, he tried a joke. He told Colbert he wasn’t very talented as an athlete, but he was useful as an “enforcer.” “You play hard, you play rough,” Spitzer said, “and hopefully you don’t get caught.”

It was an attitude he learned early on, around the dinner table. His ferocious, demanding father, Bernard, was a self-made real-estate mogul. Nightly conversation was a competitive, often brutal debate over current events. One night, according to Brooke Masters’s biography of Spitzer, during a game of Monopoly, Bernard ordered Eliot, then 7 or 8, to sell him a piece of property, then reduced his son to tears when Eliot couldn’t pay the rent. The lesson he was teaching? “Never defer to authority,” Bernard said. Bernard wanted to be Joe Kennedy; what could he have thought last week?

Spitzer was determined to live up to his father’s expectations, and to exceed them—but he could never shake completely free of his dependence on his father’s help in achieving his goals. Spitzer bankrolled his successful 1998 run for attorney general with a $5 million loan from his father, lying about the source of the money until the week before the election. The fact that it didn’t stop Spitzer from winning seems to have reinforced the belief that standard moral and ethical boundaries didn’t always apply to him.

“I don’t think it was so much about the sex,” says one man who worked closely with Spitzer for many years. “Eliot loves covert ops. He always has.”

As attorney general, Spitzer’s favorite tactic was to use shame and publicity as weapons against publicly traded companies, and for eight years, it was hugely effective—though Spitzer ran roughshod over more than a few innocent parties. His act, however, played poorly in Albany. “Richard Nixon once said it’s helpful when your opponents think you’re crazy,” Westchester assemblyman Richard Brodsky said last year. “Eliot can’t help himself, but then he rationalizes it as a tactic. What you learn is not that he’ll attack people who are with him—it’s that he’ll lie about people if it suits his purpose.”

But if Spitzer’s diatribes against legislators made him look out of control, it was his taste for the sneaky that truly undermined his first year in office. One of Spitzer’s most loyal lieutenants, then-communications director Darren Dopp, became entangled in Choppergate—the Spitzer administration’s alleged use of the state police to assemble travel records that purported to show Bruno using a state helicopter for personal business, then handing the documents to the Albany Times Union. Losing Dopp cost Spitzer an important layer of political insulation and ballast; the former aide is now facing possible perjury charges. And the Choppergate episode, besides making Spitzer look petty, ended all hope of legislative compromise with Bruno.

As Spitzer’s poll numbers plummeted, Silda Wall Spitzer asserted herself. Her husband’s disastrous first year in office confirmed all of her misgivings about political life. But she loved him too much to simply let Spitzer continue to flounder, and she believed deeply in the rightness of his cause. So Silda joined forces with Constantine to reshape her husband’s strategy. Late last year, they tried to force out Spitzer’s longtime chief of staff, Rich Baum, and pressed Spitzer to sever ties with Ryan Toohey, the political strategist running the Democratic effort to seize control of the State Senate. Constantine and Silda saw Baum and Toohey as the prime agents of Spitzer’s confrontational approach, and they wanted them booted as a signal that the governor had learned his lesson. Spitzer didn’t cut loose Baum or Toohey, but he did enlarge the roles of Constantine and his wife—a dynamic that guaranteed even more friction.

Typically, Spitzer’s courtship of Silda Wall was a challenge to be faced. They’d met in 1984, in their third year at Harvard Law School. He’d asked her out on a date; she’d turned him down. Then he spotted her with an armful of flowers on Valentine’s Day. The sight of Silda with that big bouquet made Spitzer determined to try again. This time she said yes, and three years later they were married. She put her own successful career as a New York corporate lawyer on hold indefinitely when Eliot decided, in 1994, to run for attorney general. She didn’t like the idea of becoming a political wife, but she didn’t stand in his way.

Indeed, Silda worked hard at becoming Spitzer’s political partner, and in the past few months, with her help, his political life finally seemed to be stabilizing. Spitzer had mostly softened the tone of his public pronouncements, and while the Choppergate investigation continued to churn in the background, the political momentum was shifting in his favor. On February 26, the Democrats won another seat in the State Senate, putting the party and Spitzer within one seat of taking control of the Legislature. A handful of victories in this November’s legislative races and Spitzer would finally vanquish Joe Bruno.

Yet even as his gubernatorial hand grew stronger, signs of personal trouble were growing harder to ignore. Did Spitzer even want to be governor? Every time things were looking good, he’d screw himself. One longtime close associate says that Spitzer’s drinking increased significantly. “He definitely drank a lot more, even from two years ago,” the aide says, “and much more than when he was A.G. He’s a Scotch drinker.”

Spitzer loved to back up his tough-guy credentials by saying he’d grown up “in the Bronx.” And that’s technically true. But Riverdale is a long way, in every meaningful respect, from Morrisania. Spitzer was inescapably a product of wealth, Horace Mann, Princeton, and Harvard. And it hurt when Bruno, who really did brawl his way up from poverty, taunted Spitzer as a “rich spoiled brat.” Compounding the humiliation, last year, in the midst of the greatest and most prolonged losing streak of his life, he needed help from his wife to get out of the ditch.

Spitzer, says a friend, has always been attracted to “rough-around-the-edges types, dese-dem-dose kinds of guys.” If Spitzer could never be an authentic, old-school neighborhood guy, at least his money could buy himself a taste of the edgy, subterranean life. For years Spitzer had been reckless—in his foulmouthed conversation, in his contempt for his adversaries, in his use of the power he’d been given as attorney general. But when he found himself thwarted as governor, Spitzer’s recklessness sloshed over into his personal life.

Aides were summoned to the apartment. “He told me, ‘I’m a moron. I’m a moron. I’m stupid,’” says one, who didn’t buy the explanation. “He knew what he was doing.”

By last Friday, when he read a New York Sun story detailing the Emperors Club VIP bust, Spitzer was so detached from reality that his reaction was, “Oh, that’s bad luck.” The same day, a Times reporter called his office; Spitzer instructed a spokesman to say he had nothing to do with the prostitution ring. The next day, the governor traveled to Washington once more, changing into a tuxedo in the men’s room of an Amtrak train for the annual Gridiron Club dinner, acting as if nothing were wrong. Back in New York, though, the Times was confirming the identity of Client 9. On Sunday afternoon, Spitzer finally told his wife, his daughters, and his parents the ugly truth. Or at least as much of it as he thought he needed to.

There had been hints of trouble beforehand. Sometimes Spitzer’s travel expenses greatly exceeded the normal cost of food and lodging. Maybe Spitzer was merely stocking up on hotel terry cloth bathrobes. But federal investigators are now trying to determine whether bills that now look suspicious were paid from Spitzer’s campaign accounts, or if he paid out of his own pocket for any illegal activities on road trips that seemed to be for speeches or fund-raisers.

“He likes girls,” an aide says with a shrug. “He’d notice a cute girl at a rally; he definitely has a type. But if you asked me to write 30 headlines that said what brings down Eliot Spitzer? Never in a million years.”

It remains unclear when and how Spitzer’s involvement with prostitutes began, one of many details only he knows. “He hasn’t told his wife the whole fuckin’ tale yet,” an exasperated friend said hours after Spitzer’s resignation. “There’s more.”

Many of Spitzer’s staffers have spent their entire adult working lives in his service. Last week, they were devastated. Many were seethingly angry. Everyone fixated on a different part of the bizarre tale, trying to make some sense of how Spitzer’s life had come unglued and taken theirs down with it.

“There’s something about making that girl get on a train,” said one adviser. “It seems so weird to me. I mean, there are hookers in Washington. Why did he need her to get on the train? There’s the control, making people go where you tell them. Or she was a regular. And nobody seems to know what the ‘unsafe’ is. It’s not just no condom. I don’t know what the hell it is, but that’s dumb. No guy in his right mind, even a self-destructive one, puts his dick in a hooker without a condom.”

Some resorted to black humor. “If I’d known about it, I would have stopped it,” a longtime Spitzer aide says. “Or made sure he didn’t get caught.”

“It was very funny,” says one Spitzer friend, “reading the affidavit from the woman. Client 9 was clearly Eliot. It was very much him, his personality: the micromanagement of what train she takes! The language! It was just spot-on.”

Older staffers tried to console the younger, brokenhearted Spitzer loyalists with reminders that all their work hadn’t been in vain. “It’s like I’ve had a heart attack and my heart is in pieces all over my chest cavity,” one Spitzer insider says. “This is particularly devastating for all the young campaign staffers who devoted years to him. I had someone call me this morning and say she’s devoted eight years of her life to him, and does this mean eight years of her life were meaningless? And all those brilliant assistant A.G.’s. It’s like in baseball. All those cases are going to have asterisks now: ‘Yeah, they did a brilliant case in the A.G.’s office, but it was under Eliot Spitzer, who at the time was going to prostitutes.’ And that’s terrible. The cases were not wrong. But now the bad guys feel vindicated.”

Mostly, though, Spitzer’s top staffers and close friends tried—endlessly and fruitlessly—to answer why. “I don’t know that we need to overanalyze it,” a Spitzer appointee says. “At its base it’s an old story. The additional element here of Eliot having been a public scourge of wrongdoers adds a dramatic element, but the underlying story is a rather worn-out tale of public men getting caught.”

Others, though, felt terribly, personally betrayed. “All I know of him is the guy I’ve worked for for two years,” one high-ranking staff member says. “These past two days are completely disconnected from everything I’ve ever seen or heard or known. There wasn’t a sign, even looking back. You see the time lines in the papers of when the calls were made, and nobody knew. Even Friday—apparently he was contacted by the Feds, but I noticed no change. It seems so reckless to me that there’s gotta be some psychological rationale. There’s gotta be something wrong, mentally, that at the pinnacle of your career you’d engage in behavior like this at the same time as when you’re announcing a human-trafficking law.”

Another staffer wonders if a sense of entitlement sparked the misadventure. “Maybe he was talking to one of his rich pals who said, ‘What are you doing to blow off steam?’ And Eliot’s saying, ‘Oh, shit, I wish I could blow off more steam.’ And the guy said, ‘Well, I call hookers.’ ”

The logistical particulars of Spitzer’s sexcapades are beneath pulp fiction. “It looks like what he would do sometimes is rent another hotel room where he wasn’t staying,” the friend says. “For instance, if he’s staying at the Marriott, officially, then he’d book a room in somebody else’s name at a different hotel. And he’d have a driver other than the troopers come pick him up.” One Spitzer aide has heard that in Washington a “seedy guy” who fit Spitzer’s affinity for raffish companions helped to make the assignation arrangements. On the night of February 13, though, it was Spitzer himself playing the lowlife, skulking around D.C. looking for an ATM that would dispense enough cash to pay for his date with “Kristen.”

The next morning, February 14, there was a congressional hearing on the turbulence in bond-insurance markets. New York State’s insurance commissioner was scheduled to testify. But at the last minute, Spitzer insisted on testifying himself, too. His tie firmly knotted just as his father had taught him, racing through his words, Spitzer put on a vintage performance. But the committee members couldn’t hide their surprise at his visit. The governor thanked them and caught a plane back to New York.

Less than a month later, it all came apart. On Sunday, March 9, Spitzer e-mailed Rich Baum, who was in Albany, and told him to drive to Spitzer’s apartment at 985 Fifth Avenue immediately. Constantine was summoned. “He told me, ‘I’m a moron. I’m a moron. I’m stupid,’” says one aide, who didn’t buy the explanation or the self-pity. “He knew what he was doing.” Spitzer’s older brother, Daniel, a neurosurgeon, stopped by to offer support, but also may have contributed an inadvertent insight into his brother’s attitude, and perhaps the family’s pervading arrogance. “If men never succumbed to the attractions of women, then the human species would have died out a long time ago,” Daniel Spitzer told The Wall Street Journal.

“Eliot was very lucid when I talked to him that day,” says a political adviser, laughing darkly at how logical Spitzer seemed in the middle of a mess created by Spitzer’s irrationality. “Eliot was very clear: ‘Here’s my decision tree, here’s what I’m doing.’ Silda backed him off.” Two days later, impeachment looming, Spitzer quit.

The aide is less than charitable in describing Mrs. Spitzer’s initial reaction. “Silda probably thinks, ‘I could have just been a rich Park Avenue wife, or a big lawyer. Instead, I gave ten years of my life to this political bullshit, so you’re not going to just walk away.’ It was likely a combination of that and being completely delusional: ‘I’m married to the governor of New York, and he’s the greatest thing that ever happened to this state.’ She really wanted him to fight it out.”

As Spitzer’s life unraveled last week, many of his past pronouncements were turned back on him. Given the fact that Spitzer had used wiretaps and e-mails to trap Wall Street scoundrels and yet now was being snared by the very same techniques, one quote seemed particularly haunting and prophetic. Spitzer had once been asked what advice he’d give to aspiring cheaters. “Never talk when you can nod and never nod when you can wink and never write an e-mail because it’s death,” he said. “You’re giving the prosecutors all the evidence we need.”

Certainly those words, which Spitzer also used in speeches as a laugh line, look harshly ironic now. But there’s one additional twist: Spitzer stole the remark. He updated it by adding the warning about e-mail, but the originator, whom Spitzer never credited, was a legendary turn-of-the-twentieth-century Boston ward boss named Martin “the Mahatma” Lomasney. Now, of course, he is guilty of a whole lot worse than swiping an aphorism. A career of soaring successes and even greater promise ends with Spitzer a colossal failure—not simply as a governor, but as a man.

The day after his disgrace was complete and he’d announced his resignation, ceding power to Lieutenant Governor David Paterson, Eliot Spitzer, as if to assert his independence from the rules of the ordinary world, slipped his security detail again. For an hour, no one knew where he was. He’d disappeared into the darkness.

Did the City’s Most Famous Pimp Know Kristen?
Ariel Levy on Silda Spitzer
Slideshow: Artists Interpret Spitzer’s Bad Week

Additional reporting by Geoffrey Gray and Ira Boudway.

The Governor and the Darkness