Not to be a grammar nazi, but I will anyways. There's a huge difference between then and than. Not that it matters but it's a pet peeve of mine.
When comparing one thing with another you may find that one is more appealing “than†another. “Than†is the word you want when doing comparisons.
Are you referring to this?
Hell, I'd rather gamble on DD being ultra motivated and good in a 3rd line center role then buy him out.
If so, this can be correct if he meant to hope DD is motivated, THEN plays well in a 3C role, THEN buy him out. Sure, it's completely illogical and why would we do that but grammatically I think that statement can be correct.