Category I: Statistics, Game Analysis, Odds.
Pregame.com - Daily Videos and radio podcasts with analysis from Las Vegas handicappers and bettors, as well as a forum. Handicapper picks are also sold on the site. Lots of good free betting information at Pregame.
Don Best - One of the top odds services, and they also have daily videos and a radio program. Handicapper picks sold on the site as well.
Statfox - A sports betting statistics site. They have a pay service, but the free service offers tons of statistics and analysis.
Sports Insights - Also one of the top odds services. They have a contrarian approach to analyzing games, featured in their free email newsletter, as well as in their historical data analysis and the winning results it has produced.
Category II: Pro Bettors/Handicappers with Free Information
WeCoverSpreads.com - NYC handicapper/bettor Chris Torrisi is a great source of free information. Well connected on both sides of the counter, he provides videos, podcasts, and tons of information via twitter that can help you find more winners!
ThePhillyGodfather.com - Professional bettor "PGF" gives you the information that you need to bet, and win like a real "wiseguy".
SportsBettorsClub.com - Treat your betting more like a business and not a losing hobby.
John Marks - Great NHL analysis via Youtube and twitter!