Keeper contract league trade: Hamilton for Gio + BJ

[MogulMatt1]

In leage with keeper contracts, I'm in need of another power bat this year to realistically compete and have the following offer on the table:

Josh Hamilton (contract expires at end of this year)

For

Gio Gonzalez ($14, an be kept for 2 additional years for $14, then eligible for renewal at $19+)
BJ Upton ($16, can be kept for $16 next year, then eligible for renewal at $21+ ...not considered keeper at this price) for more than one season)

My team:
Batters: Wieters, Mauer, Zobrist, Frazier, Starlin Castro, Morneau, Peralta, BJ Upton, Justin Upton, Willingham, Nelly Cruz, Choo, Matt Adams, Maybin DL: Sandoval, Desmond Jennings, Chipper Jones

Starting Pitchers: Hamels, Gio Gonzalez, Yu Darvish, Lester, Jamie Garcia, Andy Pettite, Derek Holland, Jarrod Parker, Kyle Lohse

Scoring: H2H, 5x5

I have the high end pitching depth to make this work, though I'm giving up a decent amount of keeper value, and worried about Hamilton's injury history. Do I pull the trigger?

Will hit you back.

[BadphishVt]

I really wouldn't, without knowing the details of your league, I like the idea but I don't think your pitching could really afford to lose your second best pitcher without getting someone halfway reliable back. It might be cheaper to target a 3B since your outfield is already somewhat solid. Maybe look into getting Pablo, Lawrie, or Zimmerman on the cheap, or make a stab at Beltre, any of those would be much cheaper options, would give you a similar bump in stats over the guy you'd be replacing him with. (Frazier->Beltre is more significant than Choo-> Braun in my mind)

[MaudDib]

I would only do this if this move put you solidly as the favorite to win it all. But if it just makes your more competitive then I don't think I would pull the trigger.