To me it looks like he was ready to rebuild and he wanted to conserve space on his roster. The second deal may have more overall talent.. but somewhat old and spread out. Unless those rookie picks were very high.. I would have taken number one. Phelps looks like the real deal.. not so much this year... but overall a 40 homer guy at his peak I think..

Deal one increases his roster by one player.. but deal two essentially increases his roster by four players after those rookie picks are selected.

I like his thinking.. but I would have pushed for a bigger FA upgrade. IF those rookie picks were likely to be in the top ten.. that might change my mind.