What Happens in Westchester if Astorino Wins?

Let’s play a game. It’s March 12, 2015. In a week and a half, Westchester voters will go to the polls for a special election to fill the county executive’s seat, following Rob Astorino’s upset victory for governor.

County Democrats, confident of victory with a big registration advantage at their backs and popular Astorino out of the way, threw sharp elbows during the hasty nomination fight.

idoniTim Idoni was the first to announce his candidacy, before Thanksgiving, before Cuomo’s loss had sunk in. He had been, for the previous two county cycles, the highest vote-getter among Westchester Democrats, outperforming Andy Spano in 2009 and Bramson in 2013. Well-respected among party leaders and an award-winning County Clerk, Idoni had also run up chits from local chairs as an active campaigner every year for fellow Democrats. He hoped to jump in fast and leave no oxygen for any other candidate. But questions about his fundraising chops were confirmed when his January financials showed less than $100k on hand, and his campaign never gained much traction outside of New Rochelle, Pelham, and Eastchester.

paulinAmy Paulin, who had made no secret of her interest in the job for years, announced in December, spoiling Idoni’s air of inevitability. With more than half a million dollars in the bank, a personal fortune to draw on, and a direct line to NY real estate money through her husband, Paulin was a formidable candidate. She had backed down from challenging Astorino when confronted with his high approval ratings two years earlier, but once she made up her mind, she was a determined whipper of votes. (She was one of Noam Bramson’s secret weapons during the run-up to his nomination in 2013.) But she was not universally liked by party leaders, who complained openly about her soft party allegiance.

jenkinsKen Jenkins had made the biggest mistake of his previous run for county executive before the race even began: not raising enough money to scare off other Democrats. This time around, he had quietly been making new contacts and lining up money from Cuomo funders as the governor’s key Westchester surrogate during the 2014 campaign, and was able to show an impressive $400,000 on hand when he announced his campaign with a raucous rally in January. True, his ineffective style as Board Chairman had turned off his own caucus, and he had been stuck right in the middle of feuds between Democratic factions in Yonkers. But his support among African-American voters — a critical bloc, especially for special election turnout — had never been stronger. Democrats who supported him in 2013, from Mt. Vernon to Somers, felt vindicated by Bramson’s loss that year, and were protective of Jenkins’ right to the nomination.

latimerGeorge Latimer had steadily made his way up the ranks — Rye City Councilman, County Legislator (and Chairman of the Board), State Assemblyman, State Senator. He relied on his base of powerful Sound Shore Democrats, but his history with Rye Republicans and his reach to Yonkers in the west and Bedford to the north gave him broad appeal. His 2014 re-election was much less bloody than the “slumlord” campaign of 2012, cementing his incumbancy, albeit in the Senate’s minority party. But Latimer’s habit of not making any enemies also meant he had no great friends — there were few Democratic leaders willing to go to bat for him. In fact, he never officially announced his candidacy; by keeping his fingers in both the Paulin and Jenkins pies he tried to become everyone’s second choice.

bramsonNoam Bramson, the 2013 Democratic candidate, was pushed by his fierce loyalists in New Rochelle and Mamaroneck. They cited his fundraising success of 2013, his name recognition by virtue of having already run county-wide, and his turnkey GOTV operation that would be essential in a short special election. Ironically, Astorino’s victory over Cuomo had rehabilitated Bramson’s reputation, proving that Astorino is a special candidate to whom it’s no shame losing. But though Bramson enjoyed wide regard for his intellect and ambition, many party leaders were disappointed in his ability to connect with voters outside his comfort zone.

spanoMike Spano had hoped for a different timeline to take the county’s top job, expecting to win re-election in 2015 and then challenge Astorino in 2017 (before facing his 2019 term limit as mayor of Yonkers). And whereas Spano knew he could be formidable in a Democratic primary, the special election nomination was to be decided by the party’s executive committee, most of whom still thought of Spano as a Republican and didn’t trust him to be their standard-bearer. So he played a difficult hand, trying to consolidate Yonkers against Jenkins while threatening to run on the Independent line if the Democrats wouldn’t support him. No one knew what deal he had struck to heal the rift between Doc Cavallo and the Spanos, but a legitimate third party candidacy would make the Democrats’ road to victory very bumpy.

harckhamPete Harckham, former majority leader on the County Board, had shown an ability to win in the red towns above I-287, and prepared a PowerPoint presentation for executive committee members that explained how he could redraw the map for Westchester Democrats. Harckham was backed by the Northern Coalition of local chairs, who saw this insider battle as a way to assert their influence over county politics as never before. But Harckham was hardly known among the high-turnout blue districts of southern Westchester, and no one was sure that the Northern Coalition bloc would hold.

The contest narrowed to a two-person race between Paulin and Jenkins as Paulin poached commitments from within Idoni’s base and Jenkins made deals on judgeships with northern chairs (even while Harckham tried to get his supporters to back Latimer in a second vote). Bramson, reading the tea leaves, withdrew his name and backed Jenkins, an endorsement that was hard to ignore given their hard-fought contest just two years earlier. The final blow to Paulin came when her good friend Jim Maisano was selected by Westchester Republicans to succeed Astorino — Jenkins’ team circulated a copy of a “Democrats for Maisano” advertisement used during Maisano’s 2013 re-election, on which Amy Paulin’s name appeared front and center.

Who would win the special election in Westchester between Ken Jenkins (D, WF), Jim Maisano (R, C), and Mike Spano (I)?

To be clear: Opinions expressed on this site are mine and may not reflect the views of anyone who has ever hired me (or may want to hire me). Also, I don’t write about anything on which I am actively consulting, so I may not even really know what I’m talking about.