You always thought that if there’s one job in politics worth pursuing, it’s mayor of the great city of New York. It’s the best job in politics. And given the legal and political challenges facing Mayor de Blasio, the race is likely to be wide open. The voters may have thought they were ready for a change from Bloomberg, but now they know that to have an ethical, competent government, you must elect someone who’s ethical and competent. They want someone with the skills and experience to run this city. That’s you, right?
Maybe so. But that doesn’t mean you should run, or even float your name for it. If I were seriously considering a run for mayor, I’d need to be able to answer all of these in the affirmative to even think about moving forward. (Be brutally honest with yourself in answering these.)
1) Are my politics and record palatable enough to Democratic primary voters to be competitive? How did I make my money? How will it be portrayed and considered by Democratic primary voters? In the age of Bernie Sanders, does my story fit the zeitgeist?
2) If I run as a Republican, given the registration disadvantage (7 to 1 in favor of Democrats) and given how unique and unforeseeable the circumstances were to elect both Giuliani in 1993 (massive crime + Dinkins being so awful and yet still being the Democratic nominee) and Bloomberg in 2001 (9/11 + Rudy deification and his endorsement of Bloomberg + Mark Green’s implosion), why would my candidacy be at all feasible? Joe Lhota was a very qualified candidate and fared poorly. What makes me any different?
They want someone with the skills and experience to run this city. That’s you, right?
3) Am I really rich enough to self-fund? Realistically, I’d need to spend $50 million to overcome other disadvantages. So if I’m worth $500 million, will I spend 10 percent of my net worth for a likely losing battle? Also, if I choose to accept donations, do I eliminate my strongest argument: independence? Can I afford that?
4) What’s in my background? What would a good opposition researcher or private investigator or investigative reporter find? Can I live with that, especially knowing I still probably won’t win? Do I want to risk my legacy over this? Is my family willing to endure their lives being turned upside down?
5) What does the polling say? Is there a clear path to victory based on my profile compared to the other likely candidates? Is the polling truly objective (and am I sure the pollster didn’t have a vested interest in encouraging me to run)?
6) Can I assemble a really good team? Why would anyone who knows what they’re doing choose to work for me? How do I avoid being taken for a ride by consultants just looking for a payday?
7) What do I want to achieve as mayor? Other than thinking I’d be good (and better than de Blasio), what’s my vision for the office? What’s the point of subjecting myself to all of this? What rationale do I have that would make anyone else vote for me?
8) Are there any legitimate voting blocs who would be for me (other rich people who encourage me to run during power breakfast at the Regency are not a voting bloc)? If yes, can I demonstrate that through actual data and voting patterns?
Is this more than the joy of seeing my name out there and people encouraging me? Are there other ways I can get that validation without running for mayor?
9) Am I sure this isn’t just about ego, ambition and feeling relevant? Is this more than the joy of seeing my name out there and people encouraging me? Are there other ways I can get that validation without running for mayor?
10) What makes me think that even if I win, I can successfully handle New York politics—navigate the unclear gray area between government and politics, deal with the inevitable clash with the governor, try to pass my agenda through Albany, deal with every special interest group who only cares about their agenda? Is winning actually winning? Are the skills that made me successful in the private sector skills that would work in politics?
If reading these questions alone isn’t enough to scare you off, then maybe it’s worth a closer look. But when it comes to deciding whether this is a good idea, assume it isn’t. Because most voters will.
