I am leading my division and trying to make a move to give me the best chance of winning this year. There is a team that is out of it that I am trying to work a deal with.
The way our keepers work is that we can keep them forever, and they move up 1 round each year. I have some pretty good value on some young players, Strasburg being one of them.
I am trying to move Crawford/Strasburg for Halladay/Cain. I had every intention of keeping Strasburg next season, but I feel like I need some SP help this year to compete well against the other teams making the playoffs.
My probable keepers with round kept would be: A Gonzalez(1), Holliday(2), Kemp(3), Strasburg(17), Santana(18), Hanson(19). Crawford woould be round 2, Halladay would be round 3.
With your league double counting good SP (W and QS), I'd say that Halladay and Cain have extra value and that a good rotation is key. That said, you are giving up a lot but I think it's the right move. What's that saying about championships? I can't remember it, but it's something to the effect of 'rings are forever' - you never know what will happen in a few years, and if you've got a shot to win now, you take it.
Anyway, this move is coming from the right place. Halladay is a great keeper even for a 2nd round pick. You don't say which round you'd give up for Cain, but it's probably reasonable. Gutsy move, but I say go for it.