I will be flying MAD-SAO-MIA-CLE-MAD next month. I lived in Brazil for 11 years so I am just seeing friends there. I have a suitcase or two of stuff at a friend's house in Miami I want to pick up and take back to Madrid. I will be in Cleveland for a 9-game Cleveland Guardians homestand.

I can easily survive in Brazil with just the contents of my carry-on. And I have a two-checked bag allowance from CLE to MAD.

As a lifetime Platinum on AA (thanks to 3 million miles earned), I can fly SAO-MIA-CLE with two checked bags. But I will have very little to check in when I fly the first leg. So I guess I would check in my carry-on and maybe a half-full box or a new empty suitcase.

My dilemma is that from MIA-CLE I want to check in two full suitcases with the stuff I pick up in Miami when I am there for 15 hours.

Is it possible to not hand my bags over in Miami right after Customs, repack them (i.e., fill them up to the weight allowance), and then check them later that day in order to take advantage of my two bag allowance?