In 2002, David Winer bet Martin Nisenholtz that

In a Google search of five keywords or phrases representing the top
five news stories of 2007, weblogs will rank higher than the New York Times’ Web site.

According to Workbench:

So Winer wins the bet 3-2, but his premise of blog triumphalism is challenged by the fact that on all five stories, a major U.S. media outlet ranks above the leading weblog in Google search. Also, the results for the top story of the year reflect poorly on both sides.

In the five years since the bet was made, a clear winner did emerge, but it was neither blogs nor the Times.

Wikipedia, which was only one year old in 2002, ranks higher today on four of the five news stories: 12th for Chinese exports, fifth for oil prices, first for the Iraq war, fourth for the mortgage crisis and first for the Virginia Tech killings.