Calling someone a "winner" in this context is a clear indication that they are not.
He's a winner like your little cousin's tee ball team is filled with.
He's a winner like the competitor who comes in last place in the tournament is.
"Essentially, Ogle is like a poor mans Frankie, and by poor mans, I mean like living on welfare and giving out handjobs to buy dinner poor." -MMAGoodfella