A palpable dread hung over the Democratic Party for the past week. They had lost a Congressional seat that has been in their hands since Warren G. Harding was president. Much of the reason had to do with Bill O’Reilly. Not thatBill O’Reilly, the Fox News guy, but the one that local Republicans refer to as “our Bill O’Reilly,” a genial Silk Stocking scion of conservative royalty. He was the mouthpiece for Bob Turner’s upstart campaign and the strategist who may have given the G.O.P. a template for how to end their electoral drought in New York State—and just maybe re-take the White House in 2012.

“I have rarely dealt with someone who gets it as thoroughly as he does, who stays on message and gets me and my style,” Mr. Turner told The Observer. “I am thrilled with the guy! I mean thrilled! Most of the time you want to kill these people.”

In a series of canny moves, Mr. O’Reilly took a race that seemed like a formality for the Democrat David Weprin, and pulled off an upset with national implications.

When Mr. Turner’s Democratic opponent, Assemblyman David Weprin, a longtime politician with multi-generational family ties to the district decided to skip out on a debate in the closing weeks of the race—saying that Hurricane Irene had irrevocably disrupted his schedule—it was Mr. O’Reilly who came up with the idea of sending a campaign volunteer to drive the distance between Mr. Weprin’s office and the debate site. The trip, Mr. O’Reilly gleefully pointed out, was just a few minutes door-to-door, and that the coast was clear.

“Our intrepid volunteer braved sunny skies and clear roadways this afternoon,” read the press release, “to chart the course between Mr. Weprin’s headquarters in Forest Hills and the site of tonight’s debate in Middle Village,” he wrote. “What he discovered is that, indeed, the 22-minute trip can be made, if one is willing to brave two turns and several traffic lights. Now that he knows the route, our volunteer is offering to pick up and drop off Mr. Weprin this evening—so Mr. Weprin can no longer say he can’t get there.”

It was Mr. O’Reilly too, who came up with the idea of then trailing Mr. Weprin at his public events with duck hunting whistles (Ducking. Get it?). It was also him who offered a $1,000 reward for anyone who could decipher Mr. Weprin’s position on the Palestinian Authority, after he muddled through a question about whether or not the U.S. government should give them aid. And it was his idea to pass out subway maps to Obama for America organizers when they came to volunteer on the campaign—maps that helpfully pointed out that if they made it to David Weprin’s house, they were officially lost, since he didn’t live in the district.

“You need to run against them like your life depends on it,” Mr. O’Reilly said. “You have to do it like a wild animal. You can’t do these half-assed campaigns. They are going to hold on to it with everything they’ve got. Anything less and you are not going to come close to winning.”

Indeed, no one would call the Turner campaign half-assed. “He had this ability to turn non-events into events,” Mr. Turner said a few days after being sworn in the as the newest representative from the 9th congressional district.

 

Mr. O’Reilly is a member of what may be the First Family of conservative politics. His full name is William F. Buckley O’Reilly, as in that William F. Buckley, his uncle and the founder of the National Review. Another uncle, Jim Buckley, is the only member of the Conservative Party of New York to have been elected to the U.S. Senate. His mother, Maureen Buckley, spent many years working at the National Review, handling phone calls from irate subscribers.

Mr. O’Reilly said he has eschewed mention of his pedigree.“I have been very cautious to keep this relationship under the radar,” he said. “I wanted to make sure I wasn’t a total embarrassment or flop or something.”

His mother died of a brain hemmorage while feeding an 11-month-old Mr. O’Reilly, and as a teenager, he bounced around three different prep schools in Manhattan and Westchester, eventually spending three years at DayTop Village, a drug rehab center. After getting straight, he became the face of the institution, travelling around the country to warn of the dangers of drugs, making speeches alongside Nancy Reagan in the 1980 presidential campaign.

After graduating from N.Y.U, Mr. O’Reilly tried his hand at journalism, getting an enviable posting at a local paper on Tortola in the British Virgin Islands.

“I absolutely sucked at it,” he remembered. “I couldn’t ask the questions. I didn’t want people to dislike me.”

He quit after his editor sent him to interview the bridge of a man who had shot himself in the head on his boat 48 hours after his wedding. Mr. O’Reilly walked six times around the block and told his editor that the widow declined to talk to him.

 

In part because of his lineage, and in part because of his work history, Mr. O’Reilly is part of the Old Guard G.O.P. infrastructure.This permits him to take only races he thinks he can win, even though, New York being New York, those don’t come up very often for a Republican consultant. Nonetheless, he has had a good run of late. In 2009, he helped a former sports radio jock, Rob Astorino, win the race for County Executive of Westchester, despite, a huge registration advantage for Democrats. In 2010, he helped financier Harry Wilson come within a few points of knocking off incumbent Democratic comptroller Tom DiNapoli (Mr. Wilson would have been the first Republican in nine tries to win statewide office.)

This has led to carping among some in the Republican political class. They say Mr. O’Reilly is only good when he can focus on one race at a time, and that he is still little more than a hired-hand mouthpiece, rather than someone who can help craft a campaign strategy. And they note that he has yet to make a stab at the biggest stage, by working on a Republican presidential campaign.

This last point, at least, is misguided, according to Ed Rollins, a veteran Republican strategist who helped lead the 1984 Reagan-Bush effort. In 2007, he tried (unsucessfully) to recruit Mr. O’Reilly for the Mike Huckabee campaign.

“He is every bit as talented as anybody out there,” Mr. Rollins said. “Any campaign I would put together he would be my number one draft choice.” Mr. Rollins added that the results of the Weprin/Turner race gave Republicans the sense that blue-collar Democratic votes were once again up for grabs.

Mr. O’Reilly agrees.

“Voters are available again,” he said. “After the recount in Florida, it seemed like there were a lot of Americans who were not going to be satisfied until a Democrat became president, and I think when Obama won it immediately broke the partisan spell, where people were willing to listen to the other side again. People got what they wanted. They got their next John Kennedy who was going to go a full term—hopefully—and it was a black president, a liberal president and it broke the tension.”

The reason Mr. Turner was able to exploit that willingness—and the way that Republicans can achieve something close to parity again in Blue New York, Mr. O’Reilly says—is by recruting candidates like Mr. Turner: businessmen so successful in their career that they don’t care about winning or losing and hence are willing to say what they really think.

This is not to say Mr. Turner didn’t make his share of mistakes in the campaign. He at one point expressed tepid support for federal law that would have provided medical care to 9/ 11 first responders. He would answer thorny policy questions by simply saying that he hadn’t studied up on it. At the end of the race, the campaign had only $35,000 in the bank, just as the Democrats were preparing to pour $1 million into their candidate’s coffers. (“I was praying that no reporter would ask me about it, because I would have had to dance,” Mr. O’Reilly recalled. “‘Oh, I’ll get back to you,’ one of those kinds of things.”) But he never allowed himself to get hung up on the kinds of questions about Medicare, Social Security or Paul Ryan’s budget plan that have done in other Republican candidates.

(Mr. O’Reilly managed to balance these by exploiting issues that seemed to have nothing to do with Brooklyn or Queens, like Barack Obama’s views toward Israel, or the so-called Ground Zero Mosque.)

“People cut Bob a break because he was a business guy, not a politician,” he said. “And everybody had a message to send to Obama. They were different messages, but everybody had one. And we successfully nationalized it. And then the thing was, Obama walked right into the narrative when he sent the Obama for America team into the district. I couldn’t believe the good luck. They had a memo! In ink! And so our narrative—that the race was about Obama—became true.”

Unlike many political flaks, Mr. O’Reilly is a genuinely affable guy. Most spokespeople handle the press with browbeating, intimidation, playing favorites or accusing them of bias. Mr. O’Reilly concluded an interview with The Observer by saying he needed to send flowers to a reporter who had complained about lack of access to Mr. Turner. And reporters, regardless of their political leaning, seem to actually like him, as do his Democratic opponents. It has lead to the belief among some that Mr. O’Reilly isn’t a “real” Republican.

Mr. O’Reilly admits that he doesn’t follow party orthodoxy. He is pro-gay marriage. He owns two rifles but doesn’t hunt. And he is ambivalent on abortion.

But he adds that although he used to love the battles of the campaign more, his mission in life now is to build a more conservative America.

“I have grown a very healthy dislike for the hard left. I think they are destroying the country. I think collectivism is a disaster for us. I think ‘we’ is the most dangerous word in the English language and I feel like there are not people out there battling it.”

After Mr. Turner won, over-excited Republicans like Republican Governor’s Association head Haley Barbour predicted that the G.O.P would carry New York in 2012. Mr. O’Reilly isn’t so sure. A candidate like Mitt Romney could make it close if the party poured in the resources, but he doesn’t see that as likely. What he wants is to at least make it acceptable for his fellow Republicans have a respectable presence in the state.

“When you are at a cocktail party and you are afraid to say you are a Republican, Republicans are in bad straits,” he said. “That just shows you we are willing to take a beating.”

There are two factors that led to the G.O.P’s decline in New York, in Mr. O’Reilly’s estimation. Republicans in the White House leads to a backlash in New York, since the party inevitably elects Bible Belt conservatives. And, Mr. O’Reilly says, a lot of the issues that Republicans used to run on have been solved by Republican leaders.

“We’ve been victims of our own success. [Former mayor Rudy] Giuliani ran on crime, quality of life stuff. He fixed them and then those issues were off the table. Welfare was a huge issue for Republicans and Clinton and Giuliani fixed up the welfare system and the issue went away. The Communists went away! It took us a bunch of years to get new issues—the debt, the economy, Milton Friedman vs. Keynes.”

In the meantime, the key for Republican strategists like himself is to try and drive the debate. He points with pride to his lower-taxes, less-regulation group called New Yorkers for Growth, which waged a relentless PR-campaign against the labor-backed Working Families Party. He hoped to make the group’s endorsement so toxic to Gov. Cuomo that he forsook their line in the 2010 elections, thus relegating the WFP to ballot obscurity. That gambit failed, but a key Democratic state senator decided against accepting the WFP line, and he ended up being defeated, giving Republicans control of the chamber.

“That’s a great thing. I can go to bed at night and say I was a part of that.”

For now, he can also go to be knowing that his most recent win changed the political conversation in the country. It will likely be the last competitive election until Barack Obama is on the ballot in November. In New York, the G.O.P. is gearing up for a full frontal assault, and using Mr. O’Reilly’s message as a map.

He has a note of caution for them, however.

“You are always going to lose more than you win in New York,” he said. “We are still a blue state. Only now a little less so.”

dfreedlander@observer.com

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