Like unix or linux? One person's "bucket of old shit" is another person's reliable swiss army knife that is always there when you need it.
My (admittedly very lame) anology: you're hiring a ninja assassin and have two candidates. One tells you about all the special swords and staffs and and smoke bombs he carries, the other says I just need my hands. Who do you hire?
And by the way, I would prefer the first ninja if the second one is handless.
But I absolutely know what you are talking about. I often SSH into new machines, that I may not have root access on, that may not even have internet access, or be a distro with a package manager (e.g. some switch running a custom distribution).
In those situations it is a huge advantage to know the tool, rather than try to do some gymnastics to get your tools onto the box or the data off the box.
These "old" and "broken" tools are installed as defaults on all these systems for a reason.