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If we're talking affiliates, there were two massive SE spams in the early 2000s that would have made their owners millions.
First one, the fingerprints indicated it was done by someone who owned a fairly modest link list called hornyalien.com. He was using cloaked doorways pages and on the surfer versions he'd have one of those graphical full page ads that affiliate programs used to provide, and a multi niche "money bar" on the bottom, which was very progressive for the time. From memory it was the first big spam using thousands of interlinked .biz & .info domains, which had just come out and were treated differently from regular CNOs. He took over the serps for weeks.
Second one was also cloaked spam, and he sent all his traffic to Nastydollars which was fairly new at the time and must have converted like absolute crazy with the new style tours. It was by far the biggest and most comprehensive SE spam in history, ever. It didn't matter what you searched for, there were just pages and pages of his domains. He literally took every single adult hit available from Google, shutting out every other site, and spilled into the mainstream serps as well, for at least 6 weeks. We're talking at least hundreds of millions and probably billions of hits of golden 2000s search traffic. Converting at 1:500 back in those days. Research at the time indicated he managed to get about 6 billion pages in the index.
Hats off to those great SEOs, true inspirations.
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