A "portal" built on Drupal 7. Started by someone who cannot do anything outside Drupal, and overseen by someone who believes JS to be "low level programming" (he literally said that).

What normally would be a table with 7 columns is instead 7 tables joined together. That goes for each data structure.

Each page, built in a separate module, either manually includes the same css files, or simply copy/pastes them.

Old, legacy modules have been hacked, and now depend on newer modules... Which, in turn, depend on the same old ones.

The theme contains huge, hardcoded parts of logic, so it can never be updated.

Worst part of it? It's only 3 years old. And there are people buying it as SaS. Already hitting bottlenecks at 2k users.