Worst example I can think of is an internal database at my company containing information on all employees. It gets a nightly update from HR and has an ASP.NET web service on top. Many other apps use the web service to populate things like search/dropdown fields.
The pessimism is that the developer thought that repeated calls to the web service would be too slow to make repeated SQL queries. So what did he do? The application start event reads in the entire database and converts it all to objects in memory, stored indefinitely until the app pool is recycled. This code was so slow, it would take 15 minutes to load in less than 2000 employees. If you inadvertently recycled the app pool during the day, it could take 30 minutes or more, because each web service request would start multiple concurrent reloads. For this reason, new hires wouldn't appear in the database the first day when their account was created and therefore would not be able to access most internal apps on their first couple days, twiddling their thumbs.
The second level of pessimism is that the development manager doesn't want to touch it for fear of breaking dependent applications, but yet we continue to have sporadic company-wide outages of critical applications due to poor design of such a simple component.