The Library of Alexandria
Perhaps the greatest library in history, the library of Alexandria is renowned for being a repository of historical knowledge. Therefore, the information it must have contained being lost entails the loss of books, papers, and information of value that transcends monetary value. If it had survived, the items inside would have been worth a great deal of money as well. However, it was not meant to be, and the library was destroyed by fire. What matters is which burning caused the greatest harm because the public abhorred that library so much.
More than most people think, the library was able to survive for about 1,000 years. That is perhaps older than the average library will ever be. It was also repeatedly plundered, torched, and ransacked during that time. The most well-known burning was most likely performed by Julius Caesar. Back in 48 BC, when Caesar visited Alexandria, the Egyptians resisted him. To make a point, Caesar decided to set fire to the fleet in the harbor. As a result, nearly 10% of the city's library was destroyed.
In nearly 400 years, Theophilus transformed the Serapis Temple into a Christian church. The library's books were stored in the temple, where they were later destroyed in huge numbers. When Caliph Umar conquered Alexandria in 640, it is reported that he set the bathhouses on fire for six continuous months using the library's volumes as fuel. Needless to say, it is obvious that many rare and one-of-a-kind volumes would have been lost for all time regardless of who burned the library the most over the span of several hundred years.