1) Well, as for your ignorance as to the meaning of "playing with house money," ("whatever the **** that means")I would recommend any good dictionary of American idioms. Dictionaries, you will find, are arranged alphabetically. Get back to me if you struggle with that. I would also point out that objecting to use of an expression the meaning of which you acknowledge you do not know is a little obtuse.
2) I did not say it would be "fine" if they lose. The word does not appear in my post, nor any expression remotely like it. I said in fact that I would be "disappointed" if they lose. Perhaps your struggles with the language extend beyond your difficulties with idiomatic expressions. Condolences.
3) At no point did I indicate an "assumption" that Drake would have no further opportunities, and I reject your invocation of an imaginary crystal ball. (If you have one, it is a toy.) He may or he may not have another shot. If he doesn't, I promise to be very, very sad. I hope that puts your mind at ease.
4) I wholly approve of your heroic determination not to say "fine" if we lose. Very admirable on your part.
5) Periods go inside closing quotation marks.
6) Nice Pom Poms, but the pleated miniskirt is a bit much.