Silver was born in East Lansing, Michigan, the son of Sally (nee Thrun), a community activist, and Brian David Silver, a former chair of the political science department at Michigan State University. Silver's mother's family, of English and German descent, includes several distinguished men and women, including his maternal great-grandfather, Harmon Lewis, who was president of the Alcoa Steamship Company, Inc. Silver has described himself as "half-Jewish". Silver showed a proficiency in math from a young age.

In March 2008, Silver established his blog FiveThirtyEight.com, in which he developed a system for tracking polls and forecasting the outcome of the 2008 general election. At the same time, he continued making forecasts of the 2008 Democratic primary elections. That several of his forecasts based on demographic analysis proved to be substantially more accurate than those of the professional pollsters gained visibility and professional credibility for "Poblano," the pseudonym that Silver was then using.  After the North Carolina and Indiana primaries on May 6, the popularity of FiveThirtyEight.com surged. Silver recalls the scenario: 'I know the polls show it's really tight in NC, but we think Obama is going to win by thirteen, fourteen points, and he did. ... Any time you make a prediction like that people give you probably too much credit for it.... But after that [Silver's and the website's popularity] started to really take off. It's pretty nonlinear, once you get one mention in the mainstream media, other people [quickly follow suit]'".  As a CNET reporter wrote on election eve, "Even though Silver launched the site as recently as March, its straightforward approach, daring predictions, and short but impressive track record has put it on the map of political sites to follow. The Washington Post featured Silver in its 14th annual election prediction contest this year, and he'll be reporting on Tuesday night's results with Dan Rather on HDNet".  Silver's final 2008 presidential election forecast accurately predicted the winner of 49 of the 50 states as well as the District of Columbia (missing only the prediction for Indiana). As his model predicted, the races in Missouri and North Carolina were particularly close. He also correctly predicted the winners of every U.S. Senate race. The accuracy of his predictions won him further acclaim, including abroad, and added to his reputation as a leading political prognosticator.  Barack Obama's 2008 presidential campaign signed off on a proposal to share all of its private polling with Silver. After signing a confidentiality agreement, Silver was granted access to hundreds of polls the campaign had conducted.

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