Will this trade work???

I feel its a bit loppsided in their favor because. Ortiz and Howard are very simmilar and cancel out. That leaves Rollins which jeter and Sheffield/Damon could take care of. So in turn I think you are giving 1 to many players, either pull back Sheff or Damon. I suggest to keep Damon because the Sheff has injury risk plus the Tigers are stuggling and it may be hard for him to produce.