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Jeffries’ companion at the diner that day was Louis, the journalist and television host who had unsuccessfully run for local office himself in central Brooklyn. Jeffries wanted to ask Louis about the challenges of taking on an incumbent in New York. The incumbent he had in mind was none other than Green, whom Jeffries felt had gotten captured by the system after two decades in power.
Of course, the system has its rewards: Green had thrown his support behind Louis in his challenge to longtime incumbent City Council member Mary Pinkett a year prior, a fact that would prevent Louis from supporting Jeffries, he explained to the political neophyte.
It didn’t seem to faze Jeffries, Louis recalls. He described the challenges of taking on a well-ensconced Brooklyn politician. The young man still wanted in.
A year later, Jeffries put his political stake in the ground by volunteering for an effort to rectify Brooklyn’s persistent census undercount through raising awareness about its importance and persuading residents to turn in census forms. After distinguishing himself in that effort, a group of community leaders urged him to run for Green’s seat, according to Jeffries.
From his time at the high-powered New York law firm Paul, Weiss, he utilized fundraising connections across the plush precincts of the city; in the significant July periodic disclosure report in 2000, Jeffries reported raising $50,138 to Green’s $9,550, with many of Jeffries’ top contributions coming from well-heeled individuals living in ritzy areas of Manhattan, versus Green’s coming from local unions.
The numbers caught Green’s attention.
“I really was not one that was given to raising a whole lot of money into races,” Green says. “I usually relied on my social capital and the social capital of our organizations to get us our victories, but we had to raise money, that was new.”
Jeffries also leaned on the Cornerstone Baptist Church. An usher there when he was a child, Cornerstone Baptist remains a powerful pulpit; its longtime pastor, the Rev. Sandy Frederick Ray, who died in 1979, was a close friend of the Rev. Martin Luther King Sr. MLK Jr. called him “Uncle Sandy.”
Buoyed by the money and base of support from his church, Jeffries honed a message that attacked Green as an absentee Assembly member who wouldn’t pick up the phone when his constituents called and was letting unoccupied commercial spaces in the district fester.
It wasn’t so easy to tar Green, though. He was a well-respected member of the Assembly who was advancing his priorities in a difficult political environment; in 2000, New York state had a Republican governor (George Pataki), New York City had a Republican mayor (Rudy Giuliani) and the New York state Senate was controlled by Republicans.
Over the course of the summer of 2000 — which was “chilly enough to strain good humor” and included the coolest July in New York City since 1914 — Jeffries kept pushing, walking the district every day and accepting invitations at every community forum. He honed a clever two-step that would serve him well throughout his political career: Present yourself as an avatar of generational change without endorsing the more radical politics that often go hand in hand with youth.
Former New York Gov. David Paterson remembers noticing that Jeffries had an admirable sense of poise and equilibrium: He was a young man determined to succeed and mindful of not taking positions that would dog him in future races.
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