Play Ball: A.L. East

1. New York Yankees
Best Move: Getting rid of OF Gary Sheffield and SP Randy Johnson. Both Sheff and the Big Unit had become clubhouse enigmas over the past few years and the Yanks needed to get them out. D-Town was the perfect suitor for Sheff. They were in the market for a power hitter to play DH and possibly put in some time at first base. Arizona wanted a pitcher and the trade made sense since Johnson had success there. Also, by trading the two stars, they freed up room for prospects to make an impact. That's right, the Yankees really do have prospects.
Worst Move: None. I can't think of a glaringly bad move they made. They actually did a good job by sitting on their hands this offseason and not throwing mass amounts of money in the direction of top free agents.
Season Outlook: The Yanks should do pretty good this year. Their pitching appears solid and chemistry is up. Boston and Toronto will challenge and Tampa Bay could pester them, but the Yankees are too talented to lose the division.
2. Boston Red Sox
Best Move: Signing SS Julio Lugo. Signing SP Daisuke [Dice-K is not a nickname, it is the phonetic pronunciation of his name] Matsuzaka, OF J.D. Drew and retooling the bullpen were all good moves, but signing Lugo was the best. Lugo is the 5th starting shortstop for Boston over the past 5 years. He adds speed to a line-up that previously had a lack of barn-burners. His slick glove in the field will also come in handy.
Worst Move: Not signing a veteran backup for young 2B Dustin Pedroia. Pedroia is small and fresh, and will have his setbacks. The BoSox would've been smart to go out and grab a slick fielding backup for Pedroia. In general the Sox infield depth is quite weak.
Season Outlook: The battle for 2nd place will go back and forth between Boston and Toronto, but Bostons pitching should put them on top in the end. They have a solid offense and starting pitching. The Sox big question is the bullpen. No closer has been established and their likely won't be a true closer all season. The closer candidates are RHP Joel Piniero, a former starter, and right-handed relievers Julian Tavarez, Brendan Donnelly and Mike Timlin. Piniero is the favorite, but I prefer Donnelly.
3. Toronto Blue Jays
Best Move: Re-signing All-Star OF Vernon Wells. Letting Wells walk would've been a killer for this franchise. He has been the reason this team rose from the depths of the league. He has been the reason they have been able to lure some big name free agents far North.
Worst Move: Signing SP's John Thompson and Tomo Okha. Thompson and Okha were signed to fill the fourth and fifth spots of the rotation. The problem here is that the Jays already have better, younger prospects ready to fill those spots. Signing never-have-beens to block their prospects is not a smart move for a team looking to get a playoff berth in a tough division.
Season Outlook: The Jays will challenge for 2nd place and a wild card into the playoffs, but they'll fall short. This team is just a few pieces from competing in the East. Improved hitting, especially from the shortstop spot, would help this team immensely. Toronto's well being will flow with how successful Wells and SP Roy Halladay are.
4. Tampa Bay Devil Rays
Best Move: Signing Akinori Iwamura. The Rays didn't do much this offseason. And for a team looking to get out of the 'lovable losers' label, they didn't do much to improve their standing. Iwamura should be a solid 3rd baseman, but he won't make the difference between 4th in the division and challenging.
Worst Move: Their worst move was their lack of moves. They needed to improve their bullpen, get depth at starting pitcher and get better in general. There was a wealth of relievers out there this offseason, but they didn't actively pursue any. They could've went after a second tier starter, but they didn't do that either.
Season Outlook: This is always going to be the team that has the breakout potential that never happens. Every year we hear about all the young prospects they have [this year it's OF Elijah Dukes] that are ready to bust out and save this team. If Dukes does break out, they can trade some outfielders for solid starting pitching. Otherwise, they'll be on the bottom looking up once again.
5. Baltimore Orioles
Best Move: Signing OF's Aubrey Huff and Jay Payton. Huff and Payton provide immediate pop to an offense that has lacked in that area. They also surround Miggy with actual talent. Although Payton and Huff are on the downsides of their careers, they can still be productive enough to help this team.
Worst Move: Blowing millions on mediocre bullpen arms. The signings of Jamie Walker, Danys Baez, Chad Bradford, Scott Williamson, and Jeremy Guthrie weren't bad signings. However, the money they paid for these guys is unbelievable. None of them have been or will be considered top relievers in this league yet all of them are getting paid as such.
Season Outlook: Three words: Goodbye Miguel Tejada.