Do As I Say: A Political Advice Column (06.16.14)

Q. Was the WFP smart to endorse Cuomo? 

—R.D., Bedford-Stuyvesant, Brooklyn 

A. Great question. I don’t know all the inside story. I know the top WFP operatives are savvy players. I also know that the WFP’s major labor funders threatened to stop funding the WFP if the party went with Zephyr Teachout. Finally, I know that some of these same unions—who wanted to go with Cuomo because of pending labor negotiations and other bread-and-butter concerns—have long had a nonaggression pact with Senate Republicans. So it seems that Cuomo was almost a bit player in the same drama to which he was central, if that makes any sense. In other words, while all eyes were focused on the endorsement (and Cuomo’s near-immediate walk-back of his pledges to the WFP), the real consequence of the frenetic deal-making is that in exchange for enough of the WFP’s activist base holding its nose and supporting Cuomo, the big unions have agreed to fully engage in the progressive (i.e., non-IDC) battle to regain Senate control. I don’t think anyone—even many of the WFP members pressing most vehemently for a Cuomo endorsement—believes that Cuomo will be their savior in taking back the Senate or in any particular policy area, from public campaign financing to minimum wage battles to tax policy. But the endorsement was a chit that the activist base used— probably not without orchestration by top WFP strategists—to ultimately achieve a positive if not optimal result: the full financial backing of key unions against Republican and some IDC incumbents. 

Q. Dear Professor Smith, I see that you teach classes on campaign management and have written on the political machinery, in addition to your own political career. I am wondering if you would be willing to give some candid advice regarding a potential campaign of mine. From watching the documentary about you for a fourth time, I gathered that campaign financing was your largest concern; meeting people and learning their concerns was almost a second priority. How do you develop your initial sets of funds and get your campaign off the ground? What is the best way to start introducing yourself to your perspective constituents? In the documentary it seemed you spent a considerable amount of time going door-to-door. Was this very effective? 

—R.B, Southern Illinois 

A. I’ll take your questions in order. Yes, in my congressional race—in a district of nearly 800,000 people—financing was necessarily my largest concern. Unfortunately, that’s true for any serious congressional candidate who doesn’t start a race with substantial name identification. I hated almost every moment of raising money, but I spent more time on it than I spent on anything else, even though I definitely preferred meeting regular voters and learning their concerns. (I suspect that’s true of most candidates.) 

I developed my initial set of funds by asking 13 of my closest friends, all of whom were under 35 and none of whom was wealthy, to commit to co-hosting my kickoff fundraiser and raising $1,000 each for me. Then I got out a legal pad and wrote down the name of everyone I’d ever known in my life, and put the highest dollar amount they might reasonably give next to their names, and started calling them one at a time and asking for it. Sickening, I know. But that was my first $60,000. 

In my opinion, the best way to start introducing yourself to constituents is at small (20–30 people) coffees hosted by supporters. That way you have a validator whose opinion the guests presumably trust, and the event is intimate enough that you can spend enough time with folks to really win people over and convert them into proselytizers. 

Yes, door-to-door canvassing was very effective for me. I did it every afternoon/evening for a year, except for Christmas Day, New Year’s Day and days when I had out-of-state fundraisers. It was effective because of the sheer numbers we were able to generate. With four clipboard-wielding volunteers, I jogged down the middle of the street and zigzagged back and forth across the street, only talking to “live” doors (where actual primary voters answered). Since I moved quickly and wasted no time on “dead” doors, I was able to talk with more than 100 people a night—and, combined, we were able to gather information on 400–500 people per session. The accumulation of that data gave me the best picture of the electorate of any of the candidates in my 10-way primary and nearly helped me upset the scion of the state’s then-leading political dynasty. 

Q. Hey Jeff, I work in a large congressional office and I am secretly seeing a girl who works at a desk approximately five feet from me. I’m in love with her; she likes me a lot. That’s the rub. 

She has an upcoming wedding in Spain and hasn’t invited me. It’s killing me. Whenever I’ve asked about it she gets defensive, because apparently there is some guy she used to date in Madrid. I’ve had a lot of women—not Wilt Chamberlain status, but I’m definitely no slouch—but I’m ready to settle down with this girl. What should I do to get to this wedding in Spain and convince her to forget about that guy over there, so that I can take things to the next level with her? 

—No initials, no clues(!), Washington, D.C. 

A. The two words that really tip me off to the extent of your problem are whenever and convince. Let’s start with the former. Whenever you’ve asked her about it? You mean you continue to nag her to invite you to something that she obviously doesn’t want to invite you to? That’s obviously a losing strategy and will only annoy your paramour. Second, will you convince her to forget about the other guy? No. No guy has convinced a girl she should be with him since John Cusack hoisted a boom box over his head 25 years ago. You don’t lawyer a girl into love. 

So what should you do? There’s an imbalance here—your love versus her like—and the good news is that you recognize it. The bad news is that to get back to balance—the only route to a durable relationship—you need a sea change in your attitude and behavior. In politics, undecided voters love to see a candidate fight for it. In dating, not so much. So if I were you, the first thing I’d do is find another job, if possible. Office romances are generally a nightmare, but Capitol Hill offices romances are, if possible, worse, because of the fishbowl effect. So leave before anyone catches on. That accomplishes at least two things: 1) You won’t be tempted to bug her so much, and 2) You’ll be making a broader statement to her that you don’t need to be five feet away from her 60 hours a week. 

Second, don’t ever say the word Spain again. And more generally, lose the attitude suggesting that because you’re ready to settle down, she should be. Other than bad breath and dense back hair, there are few bigger turnoffs than a sense of masculine entitlement. Instead, give her some distance and hope that she comes to the realization (of desire for you) on her own time. It sounds to me like you’ve misplayed things badly enough that the fate of the contest is no longer in your hands. Your best bet now is probably to act as happy and breezy as possible and hope that her presumed Spanish rendezvous either goes disastrously or somehow makes her miss you. 

Jeff Smith (@JeffSmithMO on Twitter) is a former Missouri state senator who resigned from office after a felony conviction and served a year in federal prison. Now an assistant professor of politics and advocacy at the New School, Jeff recently co-authored The Recovering Politician’s Twelve Step Program to Survive Crisis.