Photobucket emerged in 2003 as a revolutionary platform that made photo sharing accessible to the masses, solving a critical problem in the early digital era—how to easily host and share images online. It quickly became the backbone of personal expression on the internet, embedded in blogs, forums, eBay listings, and especially MySpace profiles. Its founders, Alex Welch and Darren Crystal, built the service from scratch into a powerhouse with over 10 billion images hosted by 2007, when it was acquired by News Corp for $250 million. However, the acquisition marked the beginning of its decline. Under corporate ownership, innovation stalled, layoffs followed, and key partnerships were lost. A pivotal moment came in 2017 when Photobucket abruptly ended free image hosting for external embedding, demanding annual fees up to $399—a move that shattered user trust and caused a mass exodus to platforms like Imgur and Flickr. The change left millions of websites, forums, and personal blogs littered with broken links, effectively erasing years of digital memories. In recent years, Photobucket has faced renewed controversy, including allegations that it sold user photos to AI training companies without consent, reigniting debates about data privacy and digital ownership. Once a foundational tool of the early web, Photobucket now exists as a shadow of its former self, serving as both a nostalgic relic and a cautionary tale about the fragility of digital platforms, the importance of user trust, and the evolving complexities of data ethics in the age of artificial intelligence.