In the
Massachusetts gubernatorial election of 1990, Silber ran for Governor of
Massachusetts as a
Democrat. His outsider status, as well as his outspoken and combative style, were at first seen as advantages in a year in which voters were disenchanted with the Democratic Party establishment. As the Democratic nominee, Silber faced
Republican William Weld.
Silber's perceived angry personality, coupled with Weld's socially liberal views, helped Weld in the race. During the gubernatorial race, Silber regularly overreacted to questions from the press. These overreactions came to be known as "Silber shockers." On the campaign trail, he called Massachusetts a "welfare magnet" and proposed cutting off benefits for unmarried mothers who have a second child while still on public aid. He questioned saving the lives of terminally ill elderly people, quoting Shakespeare and saying that "when you've had a long life and you're ripe, then it's time to go."