Seems like someone hasn't kept informed of the new CBA regulations. Even with the old regulations, Dempster wouldn't fetch two picks. With his poor season last year, he probably would be ranked in the B category of the Elias rankings, thus you wouldn't even get a 1st round pick. Now, the only way he'll fetch a pick at all is if the Cubs offer him $12.5M this off season, and he signs with another team. You can only get one pick from a team, period. It's not even a 1st round pick. It's a single pick in the compensation round. There is no sandwich pick round anymore.
Also, mid-season acquisitions in their contract years are not eligible for obtaining a compensation pick, regardless of whether or not a qualifying offer is made. Hence why there's little value being assigned to rentals this year. They receiving team will get a guy for only 2-3 months, then hold a big risk of losing him this off season with no return at all. Now, if they can work in an extension... or feel they can do so, then you might see that value change suddenly and dramatically.
So, your theories here are nonsense. If the Cubs hang onto Dempster for the sake of trying to acquire a comp pick, they would have to make him a $12.5M offer and hope someone else grants him a more lucrative deal. The again, with how much Dempster loves Chicago, he could accept the deal just to stay put. There's a real risk involved there. If you think Dempster will have the same trade value next year as he does this year, I fear you'd be miserably mistaken.
And... Sept callups don't count as an option or not. The option was burned the moment the player was sent to the minors, be it out of ST... or sent down in some other month. Options are year-long. Once you burn one, it lasts for that whole season.
