Rules are not meant to be broken—they’re meant to be exploited and wriggled out of.
Someone does something outrageous by finding a loophole in the rules, which were too narrowly written to consider such impossibilities. Loophole Abuse is a form of Refuge in Audacity—which still allows the agent to claim they were following the rules.
Sometimes the loophole doesn't even really exist, but the competitor makes everyone think it does. Occasionally the loopholes were planted to enable Loophole Abuse.
Compare Screw the Rules, I Make Them. Also contrast Bothering by the Book, where someone becomes a pest by following the rules to the letter, without looking for loopholes. If someone else finds a loophole, it's My Rule Fu Is Stronger Than Yours. Not unknown as a subversion of Just Following Orders and Exact Words. If a rule is instituted solely to close the loophole, you have an Obvious Rule Patch.
In games, this may often be the result of some kind of oversight by the creators. A programming oversight can cause someone to do something they did not actually intend, such as killing a mob intended to be invincible.
Common variants are the Animal Athlete Loophole which exists because no rule bars animals from playing sports, and Flexible Tourney Rules, wherein a characters abilities may violate the rules of the game. Scrabble Babble is Loophole Abuse for Scrabble. When applied to Tabletop Games, it becomes the annoying Rules Lawyer. See also Trying to Catch Me Fighting Dirty.
In Real Life this is rare for two simple reasons: First, loopholes are quickly closed once discovered. Second, many systems have Rule Zero: some designated referee, judge, or authority figure has the absolute final word...
A favorite weapon of the Jackass Genie.
Of course, this rarely happens in fictional instances, because of the Rule of Drama.
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