Supervisors often prefer rule breakers, up to a point

A more palatable phrasing, "supervisors prefer people that engage with the rules with purpose." That is, choosing to break a rule because you are making a cost call based on what you were able to achieve is not, necessarily, a bad thing.

The "point" where this fails, of course, is where the "cost" call above is such that the supervisor can't agree.

You sound like a supervisor there ;)

“They didn’t break the rule! They engaged in the rules with purpose unlike those rule followers.”

Though I’m not advocating your approach is incorrect.

Someone who follows the rule even when it produces a terrible outcome is a painful liability. Just like someone who breaks the rule to do the same thing.