A couple of lanes down, a young female cashier cries out. “Bloomberg is here?” she says excitedly. “Do I get a million dollars?”
The two random moments neatly encapsulate how it feels to live in Bloomberg’s New York. Through his company or his mayoralty, Bloomberg permeates every facet of city life, from the financial charts you’re studying to the healthier fat you’re eating to the skyscraper you’re welding. Bloomberg shares an appeal with that of Starbucks: the satisfaction of associating with an upscale product, even if our standard of living is declining. And many of us aspire to the mayor’s power, or at least a piece of his bank account.
Bloomberg has certainly deepened the financial bond—or dependency—through the strategic use of his checkbook. His charitable contributions have increased exponentially from when he first decided to run for mayor. In 1999, he gave away $47 million; last year, the figure was $235 million. Some of the money is funneled through the Carnegie Corporation, as supposedly anonymous gifts. Last year, 542 New York charities and nonprofits received $60 million of such gifts.
Money is a stealth weapon in Bloomberg’s political arsenal. And, as fund-raiser-in-chief, the mayor can leverage his own giving by tapping his well-heeled associates. “The mayor has an enormous influence in charity, and he does so much of it anonymously,” Rubenstein says. “I talk to some of the institutions who are clients and I say, ‘Why don’t you appeal to the mayor for money?’ They say, ‘What do you mean, appeal? He’s been funding us for years!’ I just had that discussion a couple of days ago with one of my museum clients.”
Bloomberg has also ramped up his purely political spending. Some of it is surreptitious: In 2008, three of Bloomberg’s closest friends and business associates suddenly wrote checks for $50,000 to the Working Families Party. The money was then steered to State Senate candidate Daniel Squadron, who’d won Bloomberg’s endorsement in a race to unseat a longtime incumbent.
The mayor’s dance with the Independence Party provides perhaps the best illustration of his creativity with cash. In 2001, Bloomberg attracted a crucial 59,000 votes on the Independence Party line. Four years later, he wrote a check for $250,000 and was once again rewarded with its slot, giving guilty Democrats a place to vote for Bloomberg in 2005. The cost at least doubled this year, with Bloomberg receiving the Indy and Republican ballot spots after making donations of $250,000 to each.
Lately, the Working Families Party has become a threat, so Bloomberg has used the Independence Party as even more of a conduit. In 2005, Bloomberg kicked Tom Ognibene out of the Republican mayoral primary by challenging his petition signatures. Next month, however, Ognibene will appear on the Independence ballot line thanks to Bloomberg’s blessing—because Ognibene’s opponent for a Queens City Council seat is a WFP-backed incumbent.
In mayoral-campaign seasons, Bloomberg’s wealth has a double-sided impact: He enjoys the ability to spend unlimited amounts of his own money on his reelection, and groups grateful for Bloomberg’s private donations have ample reason to support him politically, or to at least remain neutral, even though the mayor says he goes out of his way to avoid conflicts of interest in his giving. “100 Black Men came to New York for their national convention several months ago, and the national organization should be psyched that a black man is the Democratic nominee for mayor of New York City,” a Thompson operative says. “Nope; they told us they’re not interested in supporting him. Why? Could it be because Bloomberg’s company has given them money?”
Bloomberg’s wealthy friends aren’t going to be disloyal, either. Many of them have, in the past, been reliable Democratic donors. This year, though, more than 160 people who maxed out their contribution to Bill Thompson’s 2005 comptroller campaign have given him exactly zero to run for mayor against Bloomberg. The mayor’s campaign fixes the blame elsewhere. “Mr. Thompson’s fund-raising numbers are anemic because not enough people think either he should win or will win,” says Howard Wolfson, Bloomberg’s campaign communications director. “In the age of the Internet, he shouldn’t need wealthy people to raise money for him.”
Wolfson, who came up through the Chuck Schumer farm system and last year helped run Hillary Clinton’s presidential campaign, is a prime example of how Bloomberg has been able to deprive his Democratic rivals of campaign talent. Designing Bloomberg’s current get-out-the-vote ground game is Maura Keaney, whom he hired away from City Council speaker Christine Quinn. Bloomberg’s longtime lead political strategist, Kevin Sheekey, has stayed in City Hall this time around, tending to his job as deputy mayor for government affairs, but his vision still suffuses the Bloomberg campaign operation. Sheekey believes in the Colin Powell doctrine: Bring overwhelming force.