Is OTHER wrong in the post ? POST : Some context here:

I am an adult with my own income source. But his own finances are always exceptionally tight, enough so that I've needed to 'bail him out' occasionally on missed bills and such. I don't begrudge that, I know things come up, but it also makes me a bit sensitive to *waste*. 

Occasionally he will bring up that he played/paid X amount and won Y amount. Invariably, Y amount being larger than X amount. This leads me to believe that he probably plays far more than he actually tells me about - and I'm only hearing about the winnings. Often times there is some excuse offered as a pretext before the story about why it was purchased - "Oh, it was just the change from the 5 when I got a coffee." or so on.

I'll often respond by simply telling him that he probably shouldn't purchase those, that in the long run he will lose money on them. 

And he will usually respond by saying some logical fallacy - there are plenty of those. Your typical "someone has to win" or "You have to play to win" type stuff. I won't call him out directly in that sense, I feel like that wouldn't really help me make a point, but I'm not sure.

So - Am I the asshole for turning it into a negative thing when he tells me about winning? 