Three strikes and you're out? Or third time's a charm?

RObert Jackson
RObert Jackson
Photo by Rebecca C. Lewis
Robert Jackson is making his third bid for a state Senate seat.

Three strikes and you're out? Or third time's a charm?

Some candidates fizzle out after multiple failed bids. But for others, persistence pays off.
September 11, 2018

Considering the many unsuccessful candidates for public office, a career in politics seems to be only for the persistent or the self-flagellating. There’s the need to balance competing interests, the intense scrutiny by journalists (bagel orders included), and the next election looming on the horizon – threatening you with unemployment.

In Winston Churchill’s words: “In war you can only be killed once, but in politics many times."  

On Thursday, New Yorkers will vote in the primaries to see who “lives” and who “dies” as the victors lock up their party’s nominations ahead of the general elections in November. When the dust settles, will any repeat candidates fold up their campaign tents for good?

While an unusual amount of attention has been lavished on the political newcomers to the election, driven perhaps by democratic socialist Alexandria Ocasio-Cortez’s stunning victory over Rep. Joseph Crowley, there are several repeat candidates on this week’s ballot that have tried and failed before. Among them are Robert Jackson, a former New York City councilman who is trying for a third time to win a state Senate seat in Manhattan, and former New York City Comptroller John Liu, who came up short in his 2013 mayoral bid and then lost a 2014 bid for a state Senate seat in Queens that he’s seeking once again this year.

Perhaps the most notable repeat candidate is law professor Zephyr Teachout, who some have speculated appears to be the one to beat in the New York state attorney general’s race, despite a poll showing her trailing Rep. Sean Patrick Maloney and party favorite Letitia James.

But while she may still be in the thick of it in this race, Teachout has notched two losses previously. She lost a Democratic primary race against incumbent Gov. Andrew Cuomo in 2014 (picking up 34 percent to his 63 percent), and then in 2016 she winning a primary but lost the general election for New York’s 19th Congressional District against John Faso (46 percent to his 64 percent). If she wins this time around, she’ll be the state’s top prosecutor with a launching pad to higher office. But what if she loses?

City & State reached out to New York political consultants for their thoughts on what the rules are for just how many times a political hopeful can run and lose before it’s time to call it quits.

Veteran political observer George Arzt has a dire prognosis for Zephyr Teachout, if she loses. “She’s done. It’s now or never,” Arzt said. “If she loses, everyone will say, ‘Oh no! Her again!’”

It’s not uncommon for politicians to run and fail the first time if only to get their name out there. But while most are forgiven for losing their initial bid for elected office, there appears to be an nebulous calculus that sets in after that.

“If you miss that narrow window where you are exciting and people are not yet fatigued by you, then you’re gone. Your opportunity is gone,” said Arzt. “People run one, twice, or three times. I would think that’s pretty much it. Then, you can’t do it.”

Of course, sometimes the conditions can become more favorable for a repeat candidate. After Rep. Charles Rangel retired from his upper Manhattan congressional seat, Adriano Espaillat, then a state senator who had previously failed twice to unseat Rangel, finally prevailed. That win also had to do with changing demographics and the ascendency of the Dominican community as well.

How far a candidate can stretch that “narrow window” is more art than science.

“Let’s say the candidate makes a speech to a crowd and I go around the periphery of the crowd,” Arzt said. If he overhears people saying things like, “‘You know, do you think this guy could do anything? He’s run so many times’ – then I know the guy’s in trouble,” he said. But if the buzz sounds more like, “‘You know, it’s a shame this guy hasn’t won before’ – then I know the guy’s got it.”

Jerry Goldfeder, an election attorney and a mainstay of the state’s political class, waved off any kind of hard and fast rules about when a candidate should hang up their hat.

“There are no rules,” Goldfeder said. “It depends on the office. It depends on who you are as a person. And it depends on the times.”

Any number of candidates have run multiple times before finally breaking through.

“Patrick Moynihan is a good example,” Goldfeder said noting that the late U.S. senator first ran for New York City Council president and lost before winning a seat in upper house of Congress. “So what does that tell us? He couldn’t win the lower office but he won the higher office. But because it was a different time, different office, different set of circumstances.”

Another example is Mark Green, who ran unsuccessfully for the House and Senate in the 1980s before he was elected New York City’s first public advocate in 1994. “He didn’t say to himself, ‘Well, I lost for Congress, I lost for Senate, I don’t want to do this again,” Goldfeder said. “It was a perfect job for him. He ran and he won.”

Nevertheless, candidates do appear to hit a wall in the consciousness of the voters, even if there isn’t a universal rule dictating when a candidate simply can’t win a race. Some candidates might wear out their welcome more quickly than others.

The list of run-often, lose-often candidates in New York is long.

For instance, there was the New York socialist candidate Norman Thomas who ran for governor once, mayor twice, and president for six consecutive elections. Liquor purveyor Samuel Morell unsuccessfully ran for New York City Council on the Upper East Side at least 10 times. More recently, Jimmy McMillan, who created the Rent is Too Damn High Party (along with its viral music video), ran for mayor before running for governor three times in 2006, 2010 and 2014, and submitted a petition this year but fell short of signatures needed. Howie Hawkins of the Green Party is a perennial candidate who is still going strong, having run in over 20 races, including bids for the Governor’s Mansion in 2010, 2014 and an ongoing campaign this year.

On the national stage, few were more iconic than the well-regarded Harold Stassen, who ran for president nine times and was dubbed “the Grand Old Party's grand old loser.”

But there is hope for the hopelessly persistent.

Rep. Jerry Nadler started out losing a race for district leader before winning that back and serving in the Assembly for 15 years. During that time, he lost a race for Manhattan borough president, both in the Democratic primary and in the general election on a third party line, to David Dinkins. He lost again in a race for city comptroller. It was only after those setbacks that he was nominated to replace Rep. Ted Weiss – who died the day before the primary. Now a prominent congressman, Nadler – who one former Assembly speaker called a “terrible nudnik” – has gone on to win 10 consecutive elections.

Another portrait of persistence can be found in Vito Battista, a perennial candidate from Brooklyn who resorted to parading a camel and an elephant down the streets for notoriety during his six independent bids for mayor – and eventually got elected to the state Assembly.

“You gotta give credit to people who put themselves out there time and again,” Goldfeder said, “if they think they have something to give to the public.”

Correction: An earlier version of this post incorrectly said that Nadler lost to David Dinkins in the race for mayor. Nadler lost to Dinkins in the race for Manhattan borough president.

Frank Runyeon
Frank G. Runyeon
is a freelance investigative reporter in New York City.
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