Google could do it in 2000 because their search was legitimately so much better, and also because their ads were comparatively more relevant and unobtrusive than modern ads. In comparison, LLMs are relatively similar in performance unless you're picky enough that you're probably already paying and thus wouldn't be in the ad-supported tier.
That said, I wonder if ads are even lucrative enough to move the needle relative to how much training costs are increasing with each generation.
The first AI to insert blatant ads will be dumped for some other model overnight. Look at the Copilot "backlash" over their "product announcements".