Can any managers here give me insight?

Whatthefluff
My boss is very strict that if you request a day off, you have to request it at least two weeks in advance and will not honor it if you do not. The schedule is made weekly without using an algorithm, just the manager doing it. I don't understand the inflexibility. It seems intentionally inflexible. It is such a double standard because even when I've requested days off two weeks in advance they were not honored and I let the person I was trying to do a favor for down. So I really don't understand why a day off has to be at least two weeks in advance when the schedule is made weekly. Lots of things come up in a shorter time frame than that.
Can any managers here give me insight?
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