Generally speaking, modern management doesn't respect the business, they look at maximizing current P&L before all else. I worked at a place where the entire business was dependent on a true legacy system where 75% of the staff responsible for this core system retired years ago, and the rest literally died at their desks. They considered it their life's work and documented everything and advocated for a variety of sane plans to migrate.
What was the result? They're all dead. The last one was 74. The system remains, and they are paying the legacy vendor 50x and getting minimum viable support and zero enhancement, further increasing complexity. It's a shitshow for the company, but they still haven't moved to fix it. The lesson is, don't get emotionally invested in the company. That dude should have been watching his grandkids grow instead of slinging COBOL and JCL and hoping that someone would wake up and give a shit.