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This is the story of how I ran for Congress & lost. How bad? Last place. 5th out of 5. Learn how NOT to run for national office.

Funding is for the writing of the book, "How to Lose a Race for Congress."  The story is not about issues, but more about the process of how one enters a race for national office, getting on the ballot, life on the campaign trail, & all the people that you meet in between.

I ran in the 18th District of New York, one hour north of Manhattan.  The 18th has 770,000 people and includes 4 counties - Orange, Putnam, and 1/2 of Westchester & Dutchess.  There are 3 cities - Poughkeepsie, Newburgh, & Middletown.  I had offices in each city.  Newburgh in particular is known as one of the most dangerous cities in America.  I love Newburgh.

George Washington also loved Newburgh.  It was his headquarters during the Revolutionary War.  My office was across the street from his office.  Newburgh has rolling green hills & an 8 lane boulevard that meet down at a deep water port on the Hudson River.  It also has one of the highest murder rates in the country, 70% unemployment in the black community, and the police, gang & drug problems that spillover from a city living on the edge of bankruptcy.

I worked hard at developing a street team in Newburgh.  Ultimately, this backfired on me.  But for a time, I thought I had a good chance of winning Newburgh.  The MP3 song, "Hip Hop is Political," was written & performed by two of my guys on the street team.  Their rap project was kickstarted by me.  Below is the first chapter of the book.

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This is the story of how I ran for Congress and lost.

I am the Mayor of the Village of Tuxedo Park in New York State. I am a good guy who wants to do the right thing. We had a small staff, we believed, I cared, but I lost. Badly. How bad? Last place. 5th out of 5. Looking back, I was lucky there were not 10 candidates because I would have made 6-9 look pretty good. So how do you come in first in a Mayoral election, and last in a Congressional election?

Grass roots support and money. You can win a Mayoral election with grass roots support and no money. You can win a Congressional election with money, and no grass roots support. Modest amounts of either will ensure you finish somewhere in the middle. I would like to tell you that firing three campaign managers and getting fleeced by political swindlers guarantee an implosion the night before an election. But ultimately, mis-management guarantees last place.

I gained grass roots support through my work as an environmental activist in my local community. I started an organization called Tuxedo Land Trust and took on a local Town Board and a $15 billion real estate developer called The Related Companies. After numerous votes against us, it became apparent that I could become a more effective public agitator if I controlled the public agenda. So I ran for Trustee in 2010, then Mayor in June, 2011.

I got my first taste of the Tea Party in August, 2011. Our Village was set to close on a $2 million bond when the Tea Party threatened to shut down the Federal government. Municipal rates started bouncing around and we were lucky to close the deal before our local taxpayers got penalized for their grandstanding.

One month later, Hurricane Irene hit. 130,000 people in the Tri-State area lost power for 6 days. Unbelievably, our representative in Congress, Tea Party Republican, Nan Hayworth, declared that her district should not receive disaster relief until President Obama made offsetting cuts in the national budget. Think about it, six days before school starts, people are homeless and without power, and Nan wants to play political games. Sixty days later, a Halloween Nor'easter took out power again for another 6 days.

It seemed to me that we needed a Mayor in Congress. Someone focused solely on the needs of the people in their district, and not on personal ideology like Nan Hayworth. But how does a local Mayor make the leap to national office? Or, better yet, how does one go from thinking about it to actually doing it? Luck. And talking about it to everybody you run into.

My wife, whom I have known since 5th grade, worked on Democratic campaigns throughout the 1990s. First, on the Abrams campaign then on Chuck's senate run against Al D'Amato. They lost the first, won the second, and she made friends for life. One of those friends was now having their annual apple picking party at his parent's house in Greenwich, CT.

If there is one thing I have learned since becoming Mayor is that everyone wants to see your Police Badge. That's right, I have a badge, and not just any old badge. Mine is heavy and says Police Commissioner on it. Kids and men are especially keen on seeing it. Even patriarchs. And the patriarch of this house was curious about my political ambitions. I was starting to get comfortable saying it, “I am thinking about running for Congress.” His reply was even more surprising than my comfort level, “You should.” I took the leap, “yeah, I know, but I'm not really sure how to actually start.”

No problem. He raised a lot of money for Connecticut Congressman, Jim Himes. He would talk with Jim and have him call me in a few days. Yeah right. I will sit by the phone and wait for a U.S. Congressman to call me about running for national office. Three days later, Congressman Jim Himes called.

Not recognizing the number, I let it go to voice mail. Big mistake with Congressmen. They are busy people.  I would have to wait until Jim ended up in a long car ride somewhere to nowhere.  Or was it a plane trip to Hartford?  Either way, telephone tag with a Congressman is similar to being on hold with the VA's office for over 4,000 minutes.

Jim Himes is a nice guy and he graciously offered to talk with the Democratic Congressional Campaign Committee to see if they favored another candidate already. One week later, I got a call from Abby Curran, Northeast Political Director of the DCCC, asking me to come to Washington to meet with Representative Steve Israel, head of the DCCC. In 2 weeks, I went from picking apples in Connecticut to the Acela non-stop in Washington.

The DCCC in Washington is located in a non-descript, low rise near Capitol Hill. It is filled with a lot of young, smart, passionate kids who have bounced around the country working on state and national campaigns before they found their way to the show.

I was scheduled for 20-30 minute meetings with people who supposedly could provide resources for me during the campaign. It began with the DCCC Frontline Chairman. I am still not sure what this means but it turned out to be Jim Himes. We chatted briefly with his Chief of Staff in a side room about my talking points, how I was going to raise money, then I moved upstairs to meet the rest of the team.

I sat with the Northeast Political Director and listened to the Deputy Targeting Director, the Northeast Candidate Services Director, the Northeast Research Director, the Northeast Press Secretary, & the National Director take turns telling me how they could help with mass mailings, opposition research, filing reports, & dealing with unexpected media problems.

While the meetings are meant to inform a candidate of the resources available to them, I was also aware that this was interview day. I was being judged from one team to the next, worn down, watched for enthusiasm, evaluated whether I stayed on message or not, and basically just killing time until the the National Chairman was ready to see me.

We went from 8:30 to 5:00 with no lunch. Fortunately, I had two packs of Reese's peanut butter cups in my briefcase. I start every morning with a two pack and a Diet Pepsi, my can of choice.  Being on the road, my schedule was off and I held out till noon, then roughed it out with a Diet Coke from somebody's refrigerator underneath their desk. I heard Newt was getting paid a million dollars to tweet about his peanut butter cups. By the way, Newt ran twice for Congress before winning his first election.  I sure hope Newt and I never get mentioned in the same paragraph ever again, unless Reese's begins looking for a new tweeter.

Turns out we were also waiting for the National Recruitment Chairwoman, Rep. Allyson Schwartz, to come down off the hill and meet with us. By the way, Capitol Hill really is a hill. I learned this the hard way in the rain afterwards, but more about that portending later.

Steve Israel is another nice guy, and yes I am going to refer to everyone in this story as a nice person – until they're not. Also, most Representatives are people persons so it is not surprising that any encounter with them is pleasant – until it's not.

As we walked into his office, Steve motioned for Allyson and me to sit in the chairs against the wall, with Steve at the head and staff to his right. No joke, these chairs were a good 2 feet below everyone else, and uncomfortable. It was so ridiculous I had to laugh and crack a remark about now knowing who was in charge. Allyson shook her head, and told Steve he really needed to change these chairs. It occurred to me that maybe it was not deliberate. Maybe it was just a typical campaign office with the usual slapdash of chairs. Who knows, what I do know is that I killed.

We started with the inevitable, “Why do you want to run for Congress?” Turns out that I had done some opposition research myself the night before. I was actually worried that I did not know enough about national issues to stand up in public and talk about it confidently. As I scanned the internet for updates on current events, it occurred to me that I should do a search on Steve Israel.

Turns out Steve and I were on the same page. Just 2 months prior, there was a video about Steve saying we needed more Democratic candidates to run as Mayors. People were sick of politicians, and wanted problem solvers. Smile, hit stop, go to sleep. I knew how to be a Mayor.

“I want to run for Congress because we need more Mayors in Congress. We need people who are going to focus on fixing our roads, bridges, dams, sewers, & tunnels. We need people who know how to balance a municipal budget, people who don't care about ideology. Mayors know how to fix things and we don't care if you are red or blue, black or white, we just want to solve problems for people in our community.”

Big smile. “We need to make a training tape of this guy. How are you going to raise money?”

“Well, I work in Wealth Management. I went through the Merrill Lynch training program. I know how to make cold calls. I know how to hit the phones every day. I went from no book to $100,000,000 in 4 years. Raising $300,000 should be pretty easy.”

Our laconic chat riddled to a halt as Israels' orders became fast & quick.  “Call Kirsten and get her down here to meet Tom. Also, call Nita. Tom, your country needs you. How much money you tossin' in?”

“I was thinking $100,000.” I was also thinking U.S. Senator Kirsten Gillenbrand & Congresswoman Nita Lowey. Welcome to the big time.

“The quarter ends in 30 days. You should wait until January to declare, that will give you 90 days before the next FEC report. You should aim to raise $100,000 in the first 2 weeks, bank your hundred grand, then announce you've raised $200,000. That should knock 1 or 2 opponents out right away.

“I'm not sure I can do that so quickly.”

“Aim for $200,000 then settle for $100,000. Otherwise if you aim for $100,000, then...”

Steve's Chief of Staff runs in as we walk out, “Kirsten is not in town, Nita has to vote then will come down.”

“Tom, your country needs you, make me proud.”

I waited another hour in a conference room, alone, which was a nice break. I caught up on some emails, scanned Bloomberg, and then Nita walked in. Nita is a nice woman who has been in Congress for 19 years, representing Westchester County, New York. We chatted about her day, her last election against a Tea Party racist, how some Congressmen play golf every morning, her plans for dinner, and I kept thinking this person in front of me is no more qualified than I am to be in Congress. I can do this.

We walked outside and for the first time today I realized it was raining. Nita offered to have someone call me a cab, but I declined. I can do this. I waved goodbye then headed towards Washington Avenue with no umbrella. I had no idea that I would spend the next 90 minutes walking in the rain as every cab passed me by full of Capitol Hill politicos.

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