English doesn't actually bend its own grammar rules. Its notorious inconsistency comes from being three entirely different languages hiding in a single trench coat.
At its foundation, English is a Germanic language, brought to the British Isles in the 5th century by the Angles, Saxons, and Jutes. The foundational grammar and the most common daily words—like "water," "strong," and "house"—come from this Old English. However, in the 8th and 9th centuries, Viking invaders brought Old Norse. Because the two groups had to trade and live together, their languages collided. To make communication easier, English simplified its own grammar, dropping complex noun genders and word endings. At the same time, it absorbed Norse quirks and pronouns, creating the first deep layer of structural irregularity.
The real chaos began in 1066 with the Norman Conquest. French-speaking nobility took over England, making Old Norman the language of the court, law, and power, while the commoners continued speaking English. Over the next three hundred years, English absorbed around 10,000 French words. This split is why English has so many confusing spelling rules and dual vocabularies. For instance, people raise "cows" and "swine" (Germanic words used by the farmers) but eat "beef" and "pork" (French words used by the lords being served). This era also introduced French grammatical concepts, like placing adjectives after nouns in certain official titles, resulting in terms like "attorney general" instead of "general attorney."
Centuries later, during the Renaissance, scholars decided that English was not sophisticated enough. They forcefully injected thousands of Latin and Greek words into the language to describe new concepts in science, medicine, and literature. Worse, they tried to impose Latin grammar rules onto a Germanic language framework. The famous rule warning writers to "never end a sentence with a preposition" was pushed heavily by 17th and 18th-century grammarians simply because Latin sentences cannot end with prepositions. Applying that standard to English is like trying to force the rules of chess onto a game of checkers.
The inconsistency of English is simply a historical record of invasions, migrations, and academic meddling. It is not a single language that forgot how to behave, but a colliding mixture of Old English, Old Norse, French, and Latin, all fighting for dominance in the same dictionary.