Was Spitzer Destined to Fall?

By John Cloud

"His visage described discountenance." Eliot Spitzer wrote those words about a character in a short story for his high school literary magazine. The sentence was florid in an adolescent way -- Spitzer was always something of an intellectual show-off. Jason Brown, a friend from those days, later told Spitzer biographer Brooke Masters that Spitzer might simply have written, "He was unhappy."

But Spitzer's rather poetic sentence seemed apt on March 12, as he resigned as governor of New York in a brief press conference, the culmination of a 48-hour melodrama sparked by revelations that he had been a client of a prostitution ring. Thus ended a public career that had once seemed promising enough that Spitzer was discussed as a potential 2012 Democratic presidential nominee. Spitzer apologized for his "private failings," but he said nothing to explain why he would have thrown it all away, why he risked so much. He had built a reputation as an ethical crusader, and as a former prosecutor, he knew well the myriad electronic and surveillance tools that reveal hidden arrangements for crimes like prostitution. Just last year, Spitzer had signed a law that lengthened jail time for johns from three months to as much as a year.

How does a man like this expect not to be caught? George Winner Jr., a New York state senator, told the New York Times that fellow legislators, upon first hearing that Spitzer had hired a hooker, believed it was a practical joke. Says Eric Lane, a law professor at Hofstra University: "This isn't Bill Clinton, where in one sense you would have expected it. This is a shock."

But maybe it shouldn't have been. Although Spitzer had never before shown signs of a personal temperament that ran to the louche -- Masters says his treatment of past girlfriends and female employees was always respectful -- he had a long history of recklessness, a sense that the usual boundaries of authority didn't apply to him.

Part of it was being not just the brilliant son of a multimillionaire -- someone who surely sensed entitlement from an early age -- but the son of a particular multimillionaire, Bernard Spitzer. Bernard (who is in his 80s and suffering from Parkinson's) was a fierce, demanding parent. He once reduced Eliot to tears during a game of Monopoly. Bernard, a real estate developer, had ordered his son -- at the time a boy of 7 or 8 -- to sell him a piece of property; Eliot then couldn't afford the rent when a roll of the dice landed him on that property. "He didn't realize his own rights," Bernard told Masters years later, adding that he had taught his son a lesson: "Never defer to authority."

Eliot Spitzer always had a complex relationship with authority. As attorney general of New York -- the position he held for eight years before winning the governorship -- he made a name for himself by aggressively prosecuting Wall Street fraud; this magazine called him "Crusader of the Year" in 2002.

But many on Wall Street felt he went too far, pressuring ethically wayward but not necessarily criminal companies into agreeing to unfairly large settlements by threatening CEOs with prolonged legal battles. (Spitzer extracted at least $5 billion in penalties from financial firms, according to Masters.) In December 2005, former Goldman Sachs chairman John Whitehead, who was then chairing the Lower Manhattan Development Corp., alleged that Spitzer tried to bully him after Whitehead wrote a Wall Street Journal Op-Ed criticizing the attorney general's zealotry: "I will be coming after you," Spitzer allegedly told Whitehead, who said he immediately took notes of the conversation. "You will pay dearly for what you have done." (Spitzer's communications director Darren Dopp, who later left the administration under an ethics cloud, denied Whitehead's account.)

Spitzer got into trouble again just after taking office as governor. After reporters inquired as to whether Spitzer had used a state plane to fly to California for a fund-raising trip -- he had not -- Dopp asked state troopers to look into the state-funded travel habits of Spitzer's chief antagonist, Republican state senate leader Joseph Bruno. When the trooper request was made public, the state G.O.P. objected bitterly. Teams of investigators are still looking into whether the governor and his people illegally used their authority to try to intimidate Bruno.

Spitzer's approval ratings plummeted after his election; it didn't help that not long after becoming governor, Spitzer said to the Republican leader in the state assembly, "I'm a f______ steamroller, and I'll roll over you." Or that when he had a policy dispute with the popular mayor of New York City, Michael Bloomberg, Spitzer grandiosely said, "[Bloomberg] is wrong at every level -- dead wrong, factually wrong, legally wrong, morally wrong, ethically wrong."

Like many scolds, Spitzer seemed to believe his burning pursuit of right justified any personal failings -- his boorishness, the overweening use of his offices and, one presumes, his philandering. "I think he felt he was totally invulnerable and could do whatever he wanted and there would be no consequences," says Ed Koch, a former New York City mayor who considers himself a friend of Spitzer's.

Still, it's difficult to believe that the crack former prosecutor would allow himself to get caught up in the routine IRS investigation that led to the exposure of the prostitution ring. As Spitzer knows better than most, banks must inform the government of suspicious transactions like unusually large or frequent cash withdrawals and requests to break down money transfers into small amounts. (Spitzer appears to have used both methods to pay for prostitutes.) Investigators are particularly watchful when a public official is behind such transactions -- something Spitzer also would have known. During a lunch with TIME staffers a few years ago, Spitzer bragged about his extensive knowledge of wiretaps just like the one that caught him arranging his date with "Kristen."

In the end, perhaps nothing could save him from his impulses. Spitzer's sins aren't unprecedented, and if you examine the concupiscence revealed in previous scandals -- for instance, those of President Clinton, former Florida Congressman Mark Foley (who exchanged lewd messages with teenagers) and former New Jersey governor James McGreevey (who resigned in 2004 after admitting to an affair) -- it's possible to find similar biographical elements: stern father figures, highly promising early careers, an expansive sense of power and purpose. Says Masters: "It's the hubris and willingness to tackle anything that made [Spitzer] so successful, and it's the hubris and willingness not to play by the rules that seem to have been his downfall."

Politicians occasionally survive sexual misconduct, as Clinton did. Representative Barney Frank of Massachusetts and Senator David Vitter of Louisiana both stayed in office despite their prostitution scandals. Spitzer could not because, in the end, "he's got no friends," says Democratic consultant Hank Sheinkopf, who worked on two of Spitzer's campaigns. "If you're seen as being the source of all moral behavior and then you turn out not to be that way, people are happy about it."

Sheinkopf recalls a sad moment from Spitzer's 1998 attorney general campaign: Spitzer had been charged with improperly using his father's money to help finance his career. He denied the truth until the last possible moment, when he finally admitted that his dad made it possible for him to lend his campaign millions. "I looked over and saw this man -- thin, in shirtsleeves with frayed cuffs, holding himself in the corner," Sheinkopf says. "I thought, This must be the loneliest man on the planet. And in fact, he turned out to be."

With reporting by Alex Altman, Jeninne Leest. John and Alexandra Silver