1. Hardball Times Annual -- This book is a must have for any baseball fan. Straight up the best book getting published today.
2. Subscription to Paysites (Baseball Prospectus, Bill James Online, ESPN Insider or baseball-reference.com) -- These subscriptions are my favorite to give. Easy to set up and I yearly give ESPN Insider to my brother and he seems just happy with that.
3. Ron Shandler's Baseball Forecaster - Great for the fantasy nut and make sure you order from the web-site to get the digital copy and the March update.
4. Strat-O-Matic - The classic with several new additions including the Negro League set.
5. MLB game downloads - Give someone their off season fix by letting them download some of the greatest games ever. To bad the Pine Tar Game's price isn't pro-rated to get just the 1 minute of George Brett blowing up.
These are five of my best recommendations, but if anyone one else has any ideas, feel free to share. Happy Holidays.