I know two masters who did this here in my state when they'd play each other and prize money was on the line. That said, you're not going to make money playing chess for the most part. Money is in teaching and advertisements. Ultimately, both parties ended up at their rating floor of 2200. Did they make a tiny bit of money back in the day? Sure! Was it sustainable/worthwhile? Honestly, they spent way more going to those tournaments and lodging than they ever made. It doesn't really seem like it helped them or hurt anyone else that much as they arranged win/draws/losses when playing each other if it could help them win that prize fund. They got banned from at least one TD's events too. They still managed to play, but I wouldn't really call anything they did "winning".
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