Google’s supremacy in the online search advertising business is slipping. It’s a $300 billion industry that Google has dominated for nearly two decades, but that grip has been loosened by the emergence of Amazon as a search advertising threat, plus two newcomers: TikTok and Perplexity.

TikTok recently allowed advertising on its search results. And Perplexity, the AI search engine, plans to introduce ads on its search results later this month. Google, which had a 60% market share in US search advertising in 2018, is projected to have a 48.3% market share in 2025, according to the market research firm eMarketer.

Google recently lost an antitrust case that played out in federal court last year, after the government successfully argued that the tech company abused its market power to maintain a monopoly in search and search advertising — Google plans to appeal the ruling. It also recently defended its advertising technology practices in a separate antitrust battle with the government and is awaiting a ruling from a district court judge.

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