Wikipedia, the once-ubiquitous online encyclopedia, is facing a double-edged sword: the rise of AI and the decline of local media. At 25 years old, it's time to reflect on its journey and the challenges it now encounters. Wikipedia's early days were marked by a sense of wonder and skepticism. In an era before fiber-optic internet, the idea of an open-source, real-time encyclopedia was groundbreaking. But now, as we navigate the digital age, Wikipedia finds itself in a peculiar predicament. The site's popularity has waned, with human visitors declining by approximately 8% in 2025. This shift is largely attributed to the advent of large language models (LLMs) and chatbots, which are now competing for attention and, in some cases, replacing Wikipedia's role. The concern is that these AI systems are not just challenging Wikipedia's visibility but also its very foundation. As Zachary McDowell, an associate professor of communication studies, points out, the issue is akin to digital inbreeding. When AI-generated information is fed back into itself, it leads to a model collapse, resulting in errors and inaccuracies. This raises a critical question: How can we ensure that AI remains a tool for enhancing, rather than replacing, human knowledge? The financial implications of this shift are also noteworthy. Wikipedia's founder, Jimmy Wales, highlights the challenge of sustaining the site through donations, which are typically around $10. The increased demand on Wikipedia's servers from AI crawlers has led to deals with tech giants like Amazon, Meta, and Microsoft. This raises a deeper concern: as local news outlets decline, Wikipedia's reliance on them as primary sources becomes more pronounced. This, in turn, impacts the site's ability to maintain its neutrality and accuracy. The erosion of local media is not just a problem for Wikipedia but for the historical record as a whole. As Wales notes, the first draft of history is often missing, as local newspapers and news stations shut down. This is particularly evident in small towns, where the local newspaper's closure can make it challenging to write a history of the town from just 30 years ago. The 'Wikipedia detour' is not just a technical issue but a cultural one. As Google began summarizing answers on its search results page, Wikipedia's role as a gateway to information was diminished. This has implications for digital and information literacy, as people may not be encouraged to explore the citations and references that underpin Wikipedia's articles. However, there is a silver lining. Wikipedia is exploring ways to leverage AI to enhance its search experience and automate some of the more tedious tasks. For instance, AI could fix dead links in articles by suggesting potential replacements, which a human editor could then validate. This could potentially improve the quality and efficiency of Wikipedia's content. In conclusion, Wikipedia's journey over the past 25 years has been remarkable, but it is now facing a critical juncture. The rise of AI and the decline of local media are not just challenges for Wikipedia but for the very fabric of our information ecosystem. As we navigate this new landscape, it is essential to strike a balance between embracing technological advancements and preserving the core values of human-created, human-vetted knowledge. The future of Wikipedia, and by extension, our collective understanding of the world, hangs in the balance.