I've seen this happen a lot in full-time-only shops. It's possible it happens more often in shops that lean heavily on contract work, but it happens everywhere.
It takes strong technical leadership to keep that sort of technical debt quantified and prioritized without killing productivity. Especially since it's generally a huge strategic issue, but not something that generally sinks a project, department, or company overnight. So ignorant or unscrupulous leadership can run the show for extended periods of time, get promoted, and not be held accountable for making a problem worse by ignoring it.