Here are some of the transactions by guys (or ladies) who won their ESPN leagues (of the 4 I partook in in 2008):

League 1:

Trades (by month):

July: Acquired Willy Tavares in trade for Milton Bradly and David Murphy.  He needed SB and got them and it is what allowed him to get about 2 1/2 roster spots worth of SB in just two months of service time for his team.

June: Grabbed Brandon Phillips for Robinson Cano & Chien Mien Wang.  This was actually a poor trade for both sides but in the end the injury situations ended everything the trade could have been.

April: got Miguel Cabrera for Adrian Gonzalez/Jeff Kent/Andy Pettite.  MCab had himself a very good season but Adrian Gonzalez also put up surprisingly good numbers.  At the time of the trade it was amazing the winner could have even made this acquisition.

FA Additions(All by the end of May): CJ Wilson, Edinson Volquez, Nate McClouth, & Cliff Lee.  The name of the game?  Be all over the waiver wire by the end of April.  Get rid of your own personal questionable draft picks and grab everyone you can that have a great start to their season.  You never know when Cliff Lee is going to have a career year (by the way, put him on your “don’t worry about drafting this year” list).

League 2:

No Trades
FA Additions: All before May 20.  Mark Derosa*, Ryan Dempster, Ryan Ludwick, Brian Fuentes.  How Mark Derosa in a league that has both 2B & MI roster spots it is incredible he was available.  Once again Ludwick comes into the guys having a career year (not to mention getting to hit in front of a HOF hitter – So if James Loney gets to hit in front of Manny all year, he should be on your late round steals list).

League 3:
No Trades

FA Additions: Jorge Cantu on June 16.  May 29: Stephen Drew.  Apr 25: Fuentes, Jacoby Ellsbury.  Remember this (as with the Derosa pickup in the previous champion), if there is a guy in a hard to fill roster spot you really need to get him.  Even if he becomes trade bait later…it is something you can do and be happy with later.

League 4: September Pickups: Shin Soo-Choo, Jensen Lewis.  April: Derosa, Carlos Quentin, and Ryan Doumit.

You have to like these guys and they are all solid draft picks this year.  As previously stated, go after the guys starting well!