As we look ahead to the landmark 10th Skift Global Forum happening this September in New York City, today we take a look back at a panel session from Skift Global Forum 2016 correctly billed as "Legends of Online Travel". On the panel were: Brad Gerstner, Founder, Chairman and CEO of Altimeter Capital; Rich Barton, co founder and, at the time, Executive chairman of Zillow Group (he is currently CEO); Dara Khosrowshahi, then the President and CEO of Expedia (he is currently the CEO of Uber); Jay Walker, Founder of Priceline and CEO of Upside; and moderator Dennis Schaal, Skift’s Founding and Executive editor, who earlier that year had released the "Definitive Oral History of Online Travel", the authoritative account of the rise of the online travel agency.  We revisit this session from nearly 7 years ago to assess just how prescient these esteemed speakers were as they discussed the future of online travel as seen from that far away time, still 3+ years before the onset of the global covid pandemic, and 6+ years from the broad release of ChatGPT, the widely-used generative AI tool that has sparked imaginations throughout the world and travel industry. As the panelists in this session point out, many of their predictions have been around since the 1990s ".com" boom and before, so what makes now the moment? The prognostications you’ll hear in this session give us some insight into the answer, and we can be certain that this question will loom large at the coming Skift Global Forum as our sessions look to tackle the theme of “Connection in the Age of AI”.