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Current archaeological, genetic, and linguistic evidence suggests that the conquered people kept living and working beside the waves of invaders and there was a lot of intermarriage. Basically, the reason English is short on endings compared to the parent languages is that Angle/Saxon/Jute and the Scandinavian languages were very similar in vocabulary etc.. The main difference was the endings. Since people were trading and intermarrying, they developed a short-hand version of the root language without most of the endings to make it simpler. A majority of English is still based on those root words shorn of endings.

Eventually, it developed into the language that got overlayed by Norman French to become English. There were way more people speaking that germanic hodgepodge than there were Normans. Since the Normans were conquerors, the words we get from them tend to be the ones you'd use with servants. For example, beef comes from French, while cow comes from the base language.

The whole thing got blended together into something that sounded much more like German than modern English or French does. Over time, this drifted, as languages do until you get middle english, when a modern reader can actually follow, with a bit of effort. (I usually read mine out loud in a Scottish accent and it makes perfect sense. Your mileage may vary). The thing is that middle English still sounded much more like German than you'd expect. This is because an unexplained phenomenon called, "The Great Vowel Shift," by linguists. Basically, during the Tudor century, all our vowels went wonky.

Meanwhile, various academics imported a bunch of terms etc. from Latin, hence or weird Latinate borrow words from academia.

Eventually, Dr. Johnson invented the Dictionary and spellings got frozen, preserving a bunch of sounds in letters that we never use. Night and Knight used to sound different. The academics went a step further on the Latin thing and started writing grammar books telling people that "good English" means English that is more like Latin. Immigrants, especially in America, continued adding borrow words from various languages, and on it goes. Television and radio tend to iron out dialects, but shifts in pronunciation occur anyway for reasons explained and unexplained, countering that in certain regions.