It’s not as if Michael Bloomberg hasn’t done enough to establish himself as a big shot: The sprawling financial empire that bears his name now broadcasts TV and radio shows around the clock. But even he can’t help feeling a twinge of power envy when he considers a sweet gig like Mayor Giuliani’s, and the apparent right it gives him to carry on like he’s everybody’s boss. So it’s no surprise that Bloomberg has been whispering to friends that he might just try for a real loss leader of a second career -- mayor of the City of New York. And though he remains cagey about his ambitions when talking to the press, his leave-all-options-open rhetoric strongly suggests the politician within.

“I have worked in this company for sixteen years now,” he says. “But I am 55 years old, and down the road, if I had another challenge, and if it was politics, I think that would be fine.”

And 2001 could be just the year for it. With Rudy’s term expiring and a field dominated by career civil servants (who may just remind voters of Ruth Messinger), Bloomberg -- a lifelong Democrat but an untried political entity -- would look like a unique alternative.

He could also appeal to Republicans, who may have few options, especially since no Giuliani acolyte seems ready to play Bush to his Reagan. To be sure, Bloomberg has been generous with both parties. In 1996, his biggest check -- the legal maximum of $100,000 -- went to the national Democratic Party, but he chipped in $1,000 to the New York County Republican committee as well as $1,000 each to Republican presidential hopefuls Lamar Alexander and Steve Forbes.

“I have always been a registered Democrat, but I think that makes a lot more difference on a national level,” Bloomberg says with a shrug. “The fact that the mayor is a Republican, in a titular sense, is meaningless. When does that ever come up? The City Council doesn’t vote together because of party.”

He’s similarly reluctant to stake out partisan positions, even in his area of expertise, but he’s a bit more forthcoming on the subject of education. “I used to be against school vouchers. Now I think that I’d probably be a lot more in favor of them,” Bloomberg says, almost taking a position that would separate him from potential Democratic rivals. “I am a believer that the public is better off when it has a choice. The wealthy already have the choice.”

Regarding his own wealth, Bloomberg -- like private-sector-bred candidates before him -- claims that, were he to run, his fortune would guarantee his integrity. “It’s a disgrace, this attempt to buy access,” he says. “I could run and pay for the campaign myself.” But other mogul candidates haven’t fared well with New York voters. In 1989, cosmetics heir Ron Lauder blew $13 million on one of the more embarrassing mayoral bids in memory. In 1994, upstate millionaire Tom Golisano invested $10 million in his run for governor and got a return of 4 percent. Free-spending Rite-Aid boss Lew Lehrman came the closest, chalking up 48 percent of the vote in his 1982 governor’s race against Mario Cuomo.

Political insiders are split on the idea of a Bloomberg candidacy. “There are enormous liabilities to being an amateur in the business,” says consultant Norman Adler. “He’s a smart man who made a lot of money. Who cares?” But Hank Sheinkopf, who advised Fernando Ferrer on his abortive mayoral bid last year, says Bloomberg “has advantages. His name is broadcast every 30 seconds; he can raise the money. That makes him a player.”

In any case, several hurdles remain before Bloomberg could formally declare his candidacy. For one thing, he still owns 80 percent of a privately held business. When asked if he would sever his ties to the company he built, he responds stiffly, “The company would probably do even better should I cease to serve as its CEO for any reason.” Another obstacle could be his reputation as a playboy, of which he is apparently proud. “I am a single, straight billionaire in Manhattan,” he told the Guardian last year. “It’s like a wet dream.”

Still, he maintains that politicians “should be the role models for us . . . symbols of how we should lead our lives, not just people who make decisions for us.” As he says this, a watery-eyed look of idealism softens his hawklike countenance. It’s the look of an unreconstructed Eagle Scout, like something he might’ve picked up from watching Clinton. For a guy who’s too busy running a business to talk at length about running for mayor, it’s as close to a confirmation of his candidacy as we’re going to get for now.

Related:

• Archive: “Gotham: Life in the New City”
• Articles by Alex Williams
• Table of Contents: March 2, 1998 issue of New York | Subscribe!