I used to live in upstate NY. It was Mario Cuomo's loss to Pataki as governor of New York State in 1994 that most solidified my impression of the failure of a kind of electoral strategy that keeps the Democrats losing against the party that cannot govern and which I hope the movement around DailyKos can replace. The ineptness of the campaign was strange when one considers Cuomo's skill as an orator.
The most conspicuous error was a display of a lack of proportion. The campaign ads linked Pataki to Al D'Amato - over and over and over again. That linkage was the main theme of the campaign, rather than anything Cuomo had ever done or any of the many strengths he actually had. Maybe it went over in a focus group. The campaign strategists must have concentrated on the trivial but measurable statistical fact of D'Amato's high negative ratings but neglected the fact that he managed to win statewide elections.
The error that most affected me was blatant pandering to selected potential voting blocks. About two weeks before the election, Cuomo's administration hired a coordinator for gay and lesbian issues. As a gay activist at the time, I could not see it as a sincere gesture.
A particularly telling error was using the preservation of a 55mph speed limit as an issue. I see this as an example of 1) urban-based politicians neglecting rural experience; 2) politicians neglecting the problem of reducing constituents' exposure to such government intrusion as abusive speed traps, and 3) politicians looking at the quality of life in statistical terms rather than those meaningful at the moment. It is a view of citizens as pool balls determined by the outside forces of social policy rather than as autonomous, responsible individuals. Hillary Clinton's recent recommendation of a return to 55 mph shows that this is still a Democratic blind spot.