This is hardly a witty analogy here, Loretta. It's pretty common for people to describe themselves as winning or losing while playing the stock market. There's really no novel comparison here at all. It's just slightly more creative than just straight up saying "Leroy is poor at investing in the stock market". One can only try to imagine the extra, eye rolling degree of weariness that Loretta's friend/personal joke sounding board feels that this even more awful than usual attempt at a pun. As uncreative as it is, the line is still a put down so Loretta gets the point.
Official Count:
Leroy - 61
Loretta - 71
Push - 65
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