I think there are two possible options here.
If Swans win the flag, he asks for a trade at the end of the year.
If Swans don't win the flag, he stays another year to try for a Sydney flag.
This is what I get, reading between the lines, of Chad's statements.
Sydney Flag, then 2 first for Chad.
I don’t think Freo are much of a chance this year, but it’d be closer to 2 x this years firsts + 1 x future 1st to get it done this year