Bloomberg's Blues

For two-and-a-half years—from political strategist Kevin Sheekey’s first tease the night after the mayor won his second term, to his February New York Times op-ed officially ending his unofficial campaign—Michael Bloomberg denied that he was running for president.

For a few weeks after that non-campaign ended, his strategists floated the idea of the mayor as a vice presidential candidate. To add drama, they whispered that as a former Democrat and former Republican, he could align himself with either party, a number two for either Barack Obama or John McCain But that did not seem to catch on, either.

So next there were new whispers; then, more polling. Another job opportunity had surfaced for the lame-duck mayor. With two and half years to go before the next state elections, Bloomberg had apparently started considering yet another political possibility: running for governor. He may be denying the rumors with increasingly strong language, but people just cannot stop talking about the possibility. Like the previous rumors, this one keeps building despite his insistence that he has no interest in the job now held by David Paterson—and before him, by such political heavyweights as Franklin D. Roosevelt and Nelson Rockefeller.

But the politically ambitious mayor cannot stop the talk, and perhaps does not want to stop it. Collapsing cranes and still-rising rents aside, Bloomberg will likely leave office at the end of next year with remarkably high approval ratings. A new mayor will be sworn in the New Year’s Day after next, and with other people now running the show at the company he founded, Bloomberg will be out of a job.

Bloomberg does keep talking about running that foundation he created. But spending the rest of his life doling out grants and keynoting conferences just may not be enough for a man who has spent two terms setting the agenda of one of the world’s largest cities, and, to an extent, the state and country. Never one to duck the limelight—this is a man who built a media empire bearing his last name and once dated Diana Ross—Bloomberg has clearly grown used to having the cameras trained on his every word and the daily opportunity to tell the world whatever he has to say.

In the cold days of January 2010, he may come to miss that. Even at his beach house in Bermuda.

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Conveniently, there will be another election a few months later, at which point Bloomberg will be an energetic and well-cared-for 68. And unless the foundation blows through grants way too quickly, he will still have billions to spend.

So, there it is: Bloomberg for Governor. The latest trial balloon is being pumped full of the same hypothetical helium that kept his last two non-candidacies alive for so long.

But unlike the presidential campaign, an idea that somehow seemed just crazy enough to work, and that the mayor, knee-deep throughout his second term in national issues (like banning illegal guns and promoting environmental conservation) he clearly seemed to be interested in, a run for governor has many more people shaking their heads. An interesting idea, sure, and a tasty bone to gnaw on for the next 18 months; but to many political observers, this one just does not make sense. He could try, everyone seems to agree. A $20 billion fortune leaves no question about that, and his steady standing on top of the polls—he has led the last three Quinnipiac surveys on prospective gubernatorial candidates, hovering at around 30 percent—would give him a strong head start. He might even be able to win. But would he really want this job, regardless of the continuing platform it would give him in public life?

The answer, according to many who know him and have watched him as mayor, is no.

“It makes no sense,” says Democratic consultant Norman Adler. “But politically, it’s fascinating.”

Bloomberg is a manager. That was his strength in business, and that has been the root of most of his real successes over the last six years. He identifies problems, he delegates responsibilities and he looks for measurable results. Data collection is key. New services are conceived and sold as common-sense solutions.

There are always goals, but when there are grand visions, they tend to take the shape of specific plans rather than policy initiatives. When, for example, he wanted to restructure the city’s relationship with the environment, he did not just make speeches. He produced PlaNYC—127 separate initiatives all presented in a glossy, sleekly designed book, complete with colorful charts and graphs. Working on these ideas and then seeing them through is what appeals to him about city government. He has shown significantly less enthusiasm for the other parts of the job—the negotiating, the deal-making, the speeches outlining general policies proposals over which he has little actual control.

As mayor, he does not have to do much of that. As governor, he would get to do little else.

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Looking back on Bloomberg’s first interest in the 2001 mayor’s race, William Cunningham, a former advisor and communications director for Bloomberg who previously worked for Govs. Hugh Carey and Mario Cuomo, framed the possible problem.

“The job appealed to him because it was a hands-on kind of thing and you can see results fairly quickly,” Cunningham says. “The further away you get from the delivery of services to the people, the less results you see. Governors don’t have the immediate impact that mayors have—it’s a function of the job.”

But Cunningham pointed out that Bloomberg made his decision to run for mayor not after an intense investigation of the job’s official capacities; it was because of a conviction that he could do a better job.

“He didn’t really look at the city charter in terms of the actual powers,” Cunningham says. “He believed he could make a difference in the city and make the city better.”

Noting that he had no inside knowledge of the mayor’s current deliberations or the results of the internal poll, Cunningham says he expects the mayor would run for governor if he comes to a similar conclusion about what he could do as chief executive of the state.

“It’s not the title that drives him, it’s not the house, it’s not the plane,” he says. “It’s the challenge.”

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Rarely a day goes by without Bloomberg making some reference to his frustration with Albany. On matters large and small, he decries the state government’s tendency to move slowly, if at all. And though the mayor has been publicly supportive of Gov. David Paterson since the abrupt change in power in March, some of his aides have privately expressed frustration with what they see as the new governor’s disorganized leadership and bumbling staff.

These and more specific policy areas could provide challenges for Bloomberg as governor. Given the structures of state government, he would probably not be able to change much, and certainly not at the pace he has come to expect. That in itself might lure him into a job that many seem to agree is clearly not a great fit for him. Maybe. First, though, he would need to get elected.

Leaving aside his perceived reluctance to challenge New York’s first black governor or the complicated political calculus which might result from a possible musical chairs scenario between Paterson, Attorney General Andrew Cuomo and Sen. Hillary Clinton, Bloomberg would have a bigger problem if he decides to run for governor: He is a man without a party.

With a three-way presidential bid potentially on the horizon, he disaffiliated from the GOP last June and sent the Republicans on their way. To run for governor, he would probably need them back. Though the mechanics of mounting an independent run would clearly not be impossible for a man who was ready to spend millions on a nationwide ballot-access effort, running outside the GOP would create significant difficulties. As he learned from his 2001 and 2005 races for mayor, having the base of party-line voters from the GOP can be very helpful. New York Republicans are arguably in their worst condition ever, lacking any statewide official or many prospects for one of their own and the State Senate on the brink of turning blue. They may be very happy to see Bloomberg return.

State Senate Majority Leader Joseph Bruno says he is eager to have Bloomberg enter the governor’s race. In fact, Bruno says, he has been pushing the idea on the mayor for years.

“I hope he has interest in running for governor—I may have been one of the first to propose that to him way back, before he got re-elected,” Bruno says.

Bruno dismissed the idea that the mayor’s renunciation of Republicans would be a problem if he chooses to run. “Personally, I don’t think it would be,” he says, adding, “I don’t believe anybody would think it would be a problem.”

With backers like Bruno, his high name recognition, strong favorability ratings and deep pockets to fund his own race and share the wealth with down-ballot candidates, Bloomberg might be able to walk to the nomination.

“There is no question that there is drool already coming off the lips of some Republicans around the state,” says Republican consultant Tom Doherty, “because frankly, the Republican Party is not in good shape.”

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Nonetheless, if the internal party divisions that marked 2006 resurface in 2010, Bloomberg may be in trouble. That year, a groundswell of activists gave the gubernatorial nod to John Faso over the more centrist William Weld. Bloomberg’s pursuit of the GOP could be undercut by those looking for a more conservative option in an effort to keep the nomination out of Bloomberg’s progressive hands. Former Rep. Rick Lazio, who lost the 2000 Senate race to Clinton and has had some discussions with Republican officials about running for governor, could provide that option.

But in an election year without a strong right-wing alternative and when Republicans may be trying to recapture the State Senate or hold on to their majority one more time, Bloomberg may find his path to their nomination clear, so long as his checkbook remains open. His party registration switch notwithstanding, he has remained popular with many in the GOP establishment, largely on the power of his donations, including the $500,000 check he wrote to their State Senate committee in February. When Bloomberg made a surprise appearance at the New York County Lincoln Day dinner in June, he was warmly received.

Doherty predicts that the mayor’s positives for the Republicans would probably outweigh any lingering resentment, at least among those in positions of power, if not the grassroots, rank-and-file members.

“The vast majority of elected officials and party leaders will run to him as fast as they possibly could,” he says, “and I’m talking about a full-out sprint.”

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Even with the Republican nomination, Bloomberg might have trouble with the ballot. As New Yorkers are reminded every local election year, no Republican candidate has won statewide without the backing of the Conservative Party since 1974. The last one who did win without the Conservative line, however, was the Bloomberg-esque Sen. Jacob Javits, on his way to a fourth term.

His ability to massively self-finance and his strong relationship with the Independence Party could help provide the voters to compensate for lacking the Conservative line. Still, the statistic could spell trouble for a Bloomberg-for-Governor campaign, since, according to party State Chair Michael Long, the mayor would be unlikely to get Conservative Party support.

“He’d be a hard sell,” Long says. “I do not believe he possesses the Conservative Party point of view that would endear the leaders up and down the state.”

While insisting that any speculation about the 2010 race is still too early, Long says the Conservative Party’s decision to run its own candidates for mayor against Bloomberg in both 2001 and 2005 was a demonstration of how seriously the party took the ideological divide. Long warned Bloomberg to stay quiet on a preference for president, or to endorse McCain, if he’s serious about running for governor. If he backs Obama, Long says there was little chance the Conservatives would back the mayor in 2010.

“It would make it even more difficult,” Long says. “I think he would be a non-starter for Conservatives.”

Whatever his ballot lines, Bloomberg would still have to campaign. This would have its own problems: New York City, where he has won twice, has a large electorate, but it is not nearly as diverse as the whole state—geographically, demographically, politically or economically. To someone used to living and running in comparatively homogenous New York City, a statewide campaign can be a shock to the system, says Peter Vallone, the former New York City Council speaker and 1998 Democratic gubernatorial nominee.

“You go to Plattsburgh, you’re talking to people with French Canadian accents, for God’s sake. You go to Buffalo, you’re talking to people from Michigan,” he says, reflecting on his own experience. “They have altogether different problems.”

Nonetheless, Vallone says he is confident that by spending millions of dollars to buy advertisements to introduce himself to the voters, Bloomberg could pull off a win. His record as an effective champion of the city, however, could pose problems. Over the past six years, he has fought successfully for more money from the state budget, both for mass transit and public schools. With suburban and rural New Yorkers already convinced the state bends too far in support of the city, they may not look kindly on a man with such a clear commitment to the urban agenda.

Bloomberg would almost certainly run strong in the city, but if voters outside the five boroughs see him as running for governor simply to deliver for the city, they probably will not be disposed to pull the lever for him on any ballot line.

Vallone says he felt the skepticism toward him as a city official when he ran.

“You start off with major distrust,” he says.

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Winning would bring its own problems. For starters, a Governor Bloomberg would have to spend his days in Albany, 160 miles away from all his favorite restaurants and all his favorite social events, the “fate worse than death” that then-Mayor Ed Koch famously lamented at the outset of his 1982 run for governor.

Comments like that were evidence that he did not really want to be in that race, Koch now says.

“I [ran for governor] out of hubris, and people who engage in elections out of hubris deserve to lose,” Koch says.

But Koch believes Bloomberg’s moving from City Hall to the Capitol could be a more logical transition—one that he believes the mayor should consider. Though the distance between Albany and New York City might also be a turn-off for Bloomberg, Koch says the billionaire mayor’s personal fortune might take care of that problem too.

“With his planes, he could go back and forth, so there’s no problem there,” he says. “You spend part of the week in Albany and come home. Nothing wrong with that.”

Private plane or not, being governor still means a lot of days in Albany and traveling elsewhere around the state. For a man who values the flexibility of his schedule, this could pose another problem, and it’s another reason why the governor speculation still has a hollow ring to so many.

The days he does spend in Albany could themselves be unpleasant. Bloomberg has had a troubled record with state government. Though he has won greater shares of state budgets and got control of the city public school system, two signature projects—the West Side Stadium and congestion pricing—have died at the hands of the State Legislature.

Though legislators generally find him impressive, given his public comments and limited private wooing of them, many of them have the distinct feeling that the mayor actively disdains them and the Albany dysfunction he sees them as perpetuating. Attacking the status quo in Albany during a gubernatorial campaign, which many expect would have to be a central Bloomberg-for-Governor theme, would not likely help matters.

Bloomberg’s experience working with the City Council, which he has sometimes seemed to think of as a rubberstamp for his agenda may have spoiled him, according to State Sen. José Serrano, who served three years on the Council during Bloomberg’s first term before voters sent him to Albany in 2004.

The State Legislature has much more institutional power over what gets done, contains two chambers with different agendas and includes more than four times as many legislators as the New York City Council with a much wider array of political perspectives.

“The Council,” Serrano says, “is a much more manageable group.”

Serrano, who counts himself as a Paterson supporter, warned that Bloomberg might be exasperated by the differences between getting bills passed in Albany compared to getting them passed at City Hall.

“To be governor, you have to have a real ability to form coalitions and get people on board,” Serrano says. “For the executive, it is a major difference. You really cannot compare the legislative experience that you have in the City Council to the legislative experience that you have in Albany.”

Simply railing against dysfunction does not work, Serrano says. “A governor has to understand that that’s how things are in Albany right now,” Serrano says. “The way you get around that is by trying to create a coalition of the willing.”

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To some, doubts about Bloomberg’s ability to build those alliances with legislators raise a grim prospect about life under a possible Governor Bloomberg: Eliot Spitzer.

Also a strong-willed politician on a mission to remake government, Spitzer lit up hopes and dreams across the state with a well-funded gubernatorial campaign. But long before the prostitution scandal that brought him down, his combative stance toward the Legislature led to the near-total collapse of his agenda.

Although those who know Bloomberg well say there are more than enough proven differences in personality and background between the mayor and the former governor to be relatively certain that Bloomberg would not suffer Spitzer’s fate. Nonetheless, watching Spitzer’s crash-and-burn may make him think twice about treading into Albany waters—especially when he thinks seriously about who else will be in the pool. Bloomberg has had enough trouble winning over Assembly Speaker Sheldon Silver. If nothing else, the idea of the mayor having to bargain with Silver every day for every agreement is perhaps the strongest reason why most expect he will not run for governor. The prospect of a possible Bloomberg-backed Silver coup succeeding is far too low to change that dynamic.

Bloomberg’s path to being governor is far from clear. But if he wants to continue in public life, a run may be the only way. Though nearly every one of them has tried, New York City mayors have famously stumbled in their attempts to move on to something else in politics, and the only ones who did, DeWitt Clinton and John Hoffman, both got elected governor. Both are credited with some major successes in Albany: Clinton built the Erie Canal and Hoffman oversaw a period of partisan cooperation unusual for the time. Both were talked about briefly for other things.

Then again, Clinton died in office and Hoffman’s career ended in suspicion over a corruption scandal linked to Tammany Hall.

Though no one expects Bloomberg to suffer either of these fates, few really expect him to run for governor. Many who watch him closely expect that the many rumors about his hypothetical candidacy are serving a simple purpose, and they’ll be circulated so long as they keep Bloomberg from being thought of as a lame duck.

Kevin Sheekey, the deputy mayor believed to be the one fostering the rumors, called the current chatter “natural speculation.”

Asked whether he meant natural because people have an interest in seeing the mayor continue in politics or because of Bloomberg’s proven ability to fan the flames effectively, Sheekey kept his answer short: “Equal parts.”