The Chandra X-ray Observatory was launched in July, 1999 and has yielded extraordinary scientific results. Behind the scenes, our Monitoring and Trends Analysis (MTA) system has proven to be a valuable resource. With three years worth of on-orbit data, we have available a vast array of both telescope diagnostic information and analysis of scientific data to access Observatory performance. As part of Chandra's Science Operations Team (SOT), the primary goal of MTA is to provide tools for effective decision making leading to the most efficient production of quality science output from the Observatory. We occupy a middle ground between flight operations, chiefly concerned with the health and safety of the spacecraft, and validation and verification, concerned with the scientific validity of the data taken and whether or not they fulfill the observer's requirements. In that role we provide and receive support from systems engineers, instrument experts, operations managers, and scientific users. MTA tools, products, and services include real-time monitoring and alert generation for the most mission critical components, long term trending of all spacecraft systems, detailed analysis of various subsystems for life expectancy or anomaly resolution, and creating and maintaining a large SQL database of relevant information. This is accomplished through the use of a wide variety of input data sources and flexible, accessible programming and analysis techniques. This paper will discuss the overall design of the system, its evolution and the resources available.