Michael Bloomberg is endorsed for New York City mayor by Rudy Giuliani on Oct. 27, 2001. (Photo:AP)
January 30, 2020 by David Silverberg
It’s a bold, audacious strategy: Put all your chips on Florida. Ignore or avoid all the other primary contests. With your name recognition, vigorous campaigning and votes from transplanted northerners you can take Florida. Then the other primary states will fall into line, you’ll be the party’s nominee and you’ll be on your way to the general election and the White House.
It makes sense: it avoids all the complications of the early contests, it reduces your campaign costs and you can run a ring around a crowded field to a smashing victory.
That’s certainly what Rudy Giuliani thought in 2008.
It’s what Mike Bloomberg thinks in 2020.
And so, he’s doing the dance again. Let’s call it “the Florida sidestep.”
The parallels between Giuliani and Bloomberg are striking: Both were New York City mayors and relative outsiders to their parties. To both Florida seemed—and seems—a fruit ripe for plucking.
What can Rudy Giuliani’s experience tell us about what awaits Mike Bloomberg? How much does the past inform the future?
It’s time to compare and contrast!
The Giuliani bid
In 2007, as today, the field was crowded. President George W. Bush had reached his term limit and there was a massive scramble in both parties to replace him.
On the Republican side names kept popping up and falling by the wayside: George Allen, Tommy Thompson, George Gilmore, Sam Brownback, Duncan Hunter, Tom Tancredo, Fred Thompson, John Cox.
Anyone remember Alan Keyes?
Among the more credible Republican candidates were US Senator John McCain of Arizona, Massachusetts Gov. Mitt Romney, Arkansas Gov. Mike Huckabee, and Rep. Ron Paul of Kentucky.
But by January 2008 Rudy Giuliani loomed over all of them.
Giuliani was widely hailed as “America’s mayor.” On Sept. 11, 2001 he had led his city and rallied the country in the face of the worst terrorist attacks ever perpetrated on the American homeland. He stood out as a tower of strength, competence and calm amidst chaos and horror. The nation’s admiration for his performance on that day was virtually universal. He’d been named Time’s Man of the Year in December 2001. He was respected, admired and adored.
(For a full account of Giuliani’s actions on 9/11, see “Calm Amidst Chaos: Rudy Giuliani and 9/11” from the book Masters of Disaster: The Political and Leadership Lessons of America’s Greatest Disasters.)
Giuliani and his team thought he could ride his fame and respect into the White House and it was a reasonable expectation.
That year the election season started early: the Iowa caucuses were on Jan. 3. Huckabee led with 34 percent of the results followed by Romney, Fred Thompson and McCain. Giuliani came in a distant sixth with 4 percent. In New Hampshire on Jan. 8, McCain beat Romney for first place, with Huckabee beating Giuliani for third place by 11 percent to 9 percent.
The disappointing results in these early, rural, very conservative states didn’t faze Giuliani or his team. Giuliani led the national polls in February and by March he was considered the frontrunner, despite the early setbacks.
After Iowa and New Hampshire the different candidates focused on widely different primaries. Giuliani bet big on Florida, whose primary was Jan. 29. He was going to use victory there as his stepping stone to a massive win on Super Tuesday, Feb. 5.
Florida seemed by all logic to be Giuliani country: There were hundreds of thousands of transplanted New Yorkers, especially on the east coast. They knew and presumably loved him. He had a 20-point lead in the polls. He concentrated his campaigning and resources early in the year and his rivals didn’t start their Florida campaigns until late in the month. Rallies around the state were well-organized long in advance of the primary. Media attention, both national and local, continued to focus on him and his presidential prospects.
And yet, Giuliani didn’t catch fire. His rallies were sparsely attended. The vigor and enthusiasm emptied out of his campaign like gas leaking from a balloon. Other candidates raced down to Florida to campaign. At the last minute Florida Gov. Charlie Crist endorsed McCain.
In the end, McCain won Florida with 36 percent of the vote, reaping all the state’s 57 delegates to the Republican convention. He was followed by Mitt Romney with 31 percent and Giuliani trailing with only 14 percent.
The next day Giuliani dropped out of the race.
The Bloomberg bid
This year Michael Bloomberg got into the Democratic race on Nov. 24, much later than his Democratic rivals, who at their greatest extent included 25 candidates. He has not participated in any Democratic debates and he is not going to be on the ballot in any of the early primary elections.
Instead, Bloomberg is concentrating on key battleground states in the later rounds of primaries: California, Texas—and Florida.
“The road to the White House goes through Florida, is the saying,” Bloomberg told the Miami Herald. “That’s probably true.”
What ground Bloomberg lost with his late entry, he is trying to make up with heavy television advertising, a very professional campaign organization and a lot of spending. In January he spent $14.3 million in Florida, according to Politico. In December he spent about $2 million a week. He’s been hiring staff who worked on the campaign of Tallahassee mayor and gubernatorial candidate Andrew Gillum.
Then and now
There are some very significant differences between the Bloomberg campaign and Giuliani’s 2008 effort.
The first is the calendar. In 2008, the Florida primary preceded Super Tuesday when 24 states and American Samoa held their primaries on the same day. Giuliani viewed Florida as a stepping stone.
This year the process is reversed. Florida’s March 17 primary follows Super Tuesday on March 3 when 15 states and Democrats abroad vote. As a result, the nominee may already be known by the time Floridians go to the polls. However, if Super Tuesday doesn’t settle the matter, Florida very well could be the state that does.
So if Florida was a stepping stone in 2008, it could be the capstone in 2020.
Also, while Bloomberg is skipping the initial four primaries, he can’t ignore or write off all the pre-Florida primaries the way Giuliani did. In addition to California and Texas, Bloomberg is investing in other Super Tuesday states.
Bloomberg is not precisely following the Giuliani model. Nonetheless, there are interesting parallels between the two men and their campaigns.
The commonalities
Some of Giuliani’s and Bloomberg’s shared characteristics are blindingly obvious: Both are New Yorkers and both served as the city’s Republican mayors.
Fun historical fact: Sept. 11, 2001 happened to be New York City’s mayoral primary day. Rudy Giuliani was limited to two terms and was stepping down. Because of the terrorist attacks, the primary was postponed (to the best of this author’s ability to determine the only time in American history that an election has been postponed, including during wartime).
After the attacks, Giuliani wanted to stay on as mayor and there was some support for the idea given the city’s challenges. Initially, he wanted the term limits lifted so that he could run for a third term. For all the adoration he was receiving and for all his supporters’ efforts to change the law, the state legislators who held the power to make the alteration were unalterably opposed. To them and much of the media, it seemed like a naked power grab.
With this third term hopes dashed, Giuliani attempted to have his term extended by three months. Two of the three mayoral candidates hoping to replace him agreed to the three-month extension. The third, Fernando Ferrer, refused. The state legislature also refused to condone it.
Ultimately, with great reluctance and little grace, Giuliani gave up his efforts and endorsed the Republican nominee for mayor: Michael Bloomberg, who won the general election and took office on Jan. 1, 2002.
In addition to Giuliani and Bloomberg’s obvious commonalities there are other, related ones: both men are essentially political centrists and both are outliers in their respective parties.
Whatever he may be today, in 2008 Giuliani was essentially a center-rightist. He’d been tough on crime in New York before 9/11 made him the nation’s foremost anti-terrorism crusader. Nonetheless, when he ran for the Republican Party’s presidential nomination he was viewed by the Party faithful as a big-city, anti-gun, social liberal. He’d had dysfunctional family relationships and been married three times, which made evangelicals uncomfortable.
As his rival Mitt Romney put it at the time: “I don't think the Republican Party will choose a pro-choice, pro-gay civil union candidate to lead our party.”
Romney was right. Giuliani didn’t sit well at all with the Party activists who decided primaries, especially in Florida. And all those transplanted New Yorkers he was counting on? They were all Democrats.
For his part, Bloomberg started political life as a Democrat, in 2001 switched to Republican to run for mayor and became an Independent in 2007. Last year he became a Democrat again and is now running for the Democratic presidential nomination.
Long-time Democrats can be forgiven if they are somewhat skeptical of his political loyalties.
Most Democrats are also suspicious of Bloomberg’s wealth. Prior to his political career he built his fortune through Bloomberg LP, a global financial services, software and mass media company that made him the eleventh richest person in the United States with an estimated fortune of $60.5 billion in 2020, according to Forbes.
It’s that kind of wealth that allows him to make his self-financed presidential bid. But it doesn’t sit well with a party trying to mobilize the economic 99 percent and it also opens him to charges of trying to buy the election.
For all their differences and party allegiances, both Giuliani and Bloomberg share core values born of New York City realities: social tolerance leavened with an emphasis on law and order; support for immigrants and immigration; a global outlook; laissez-faire business encouragement; and a simple, pragmatic belief in common-sense good governance.
The BIGLIEST difference…
Into this mix in 2016 came yet another New Yorker: Donald J. Trump. His political presence marks the biggest difference between 2008 and 2020.
It is interesting that Giuliani, Bloomberg and Trump all worked with each other in New York, doing deals, moving in the same social circles and boosting the city. They know each other well and all come out of the same cauldron. They’re also all of the same generation: Giuliani is 75 years old, Bloomberg 77, Trump 73.
In 2008, Trump was a political nonentity who had no impact on the presidential race. Eight years later, Trump propelled Giuliani and Bloomberg in different directions.
In 2016, Giuliani signed on to the Trump team, campaigned for him and evolved (or devolved, depending on your perspective) into a Trump “killer lawyer”—a fixer and factotum, defender and deal maker. Submitting to his master’s whims and delusions, in the eyes of most of the sane world Giuliani appears today as a Trump puppet and enabler, a toadying sycophant and slavish servant whose behavior even Trump sometimes regards as bizarre. According to author Michael Wolff in the book Siege, Giuliani volunteered to work for Trump for free when the president was under investigation by Robert Mueller (as opposed to lawyer Alan Dershowitz, who demanded $1 million per month and was initially refused).
Bloomberg, by contrast, saw the danger Trump presented from the time that Trump launched his campaign. It was the reason that he addressed the Democratic National Convention in support of Hillary Clinton in 2016.
Michael Bloomberg addresses the 2016 Democratic Convention
“I’m a New Yorker, and New Yorkers know a con when we see one!” Bloomberg memorably said in that speech. “Truth be told, the richest thing about Donald Trump is his hypocrisy.” He warned that Trump, whom he called “a dangerous demagogue,” threatened America’s economy, trade and unity.
“The bottom line is: Trump is a risky, reckless, and radical choice. And we can't afford to make that choice,” he warned.
But by whatever magic, that was the choice that was made and Bloomberg has not let up in his opposition to Trump.
“I’m running for president to defeat Donald Trump and rebuild America,” he stated in the announcement of his 2020 campaign. “We cannot afford four more years of President Trump’s reckless and unethical actions. He represents an existential threat to our country and our values. If he wins another term in office, we may never recover from the damage. The stakes could not be higher. We must win this election. And we must begin rebuilding America.”
On a more pragmatic basis, Bloomberg apparently fears that the Democratic center cannot hold during the primary process and Trump may win the general election. And so he entered the race.
So will it play in Florida?
Polls, both national and statewide, will be going up and down between now and the presidential primary and the only one that counts is the one on Election Day. That said, a St.PetePolls.org poll of 2,590 likely Florida Democratic presidential primary voters conducted on Monday and Tuesday (January 27 and 28) found Bloomberg coming in second behind former Vice President Joe Biden by 41.3 percent to 17.3 percent.
Apparently those TV ads are having an impact.
Bloomberg’s spending could make possible the Florida sidestep strategy that Rudy Giuliani was unable to implement in 2008.
Ironically, the biggest factor in Bloomberg’s candidacy may not be Bloomberg—but Trump. If Trump remains in office despite impeachment he will feel he has "won" and is likely to claim complete exoneration. With a sense that he has no restraints or restrictions, his actions and statements are likely to become even more dangerous, daring and deranged and he just may drive Florida Democrats toward Bloomberg’s centrism.
Regardless of whether the strategy works, Bloomberg is certainly right about one thing: Donald Trump represents an existential threat to democracy and the future of the United States.
Can Bloomberg build sufficient support to overcome the kind of party opposition to his campaign that Giuliani faced in 2008? Can Bloomberg beat Joe Biden in the Democratic fight for the center? And can he get the nomination?
This year it’s Florida’s Democratic voters who may hold the answer.