One winning bet, three losing bets, and one election won.
First, my winning bet. In July, I bet a local prominent Republican, Peter Newman, $50 that Obama would be re-elected.
Second, my three losing bets.
1. Last week, I bet Scott Sumner what he called "reputation points," where he gave me 70-30 odds. My bet was that Romney would win at least 280 electoral votes. Since it's about reputation, let me say that I am humbled. I bought too much of the "the crowds for Romney are large and energetic and therefore Romney will do well on turnout" spin. I remember Mondale, in 1984, making the same mistake I made.
2. At a conference in Miami this weekend, I bet Washington State University, Vancouver political science professor Carolyn Long that Obama would get fewer than 280 electoral votes. Of course, I lost. She gave me 5-3 odds. I would have won $100. Instead I owe her $60.
3. At the same conference I bet her that the Democrats would not make a net gain in the Senate. Even odds. I owe her $50.
Third, the election outcome I helped win. A friend and retired lawyer, Carl Mounteer, and I wrote the ballot argument against a property tax increase in Pacific Grove. The measure, Measure A, needed 66.7% to win. We got 34.95% and so squeaked out a narrow win. My gut told me that we would get 38% but in the last couple of days I revised that downward to 36%. I was close. BTW, a switch of 108 votes would have caused us to lose. Going by the number of pro-A signs and the pro-A mailer I received, I estimate that, if you leave out our time value for writing the ballot argument and writing a local newspaper op/ed and two letters to the editor, we were outspent by over 200 to 1.