This never would have happened with a headphone jack.

I call shenanigans on this statement. This exact scenario with a 3.5 mm would have seen the copper inside the connector break from stress. As someone who went through the evolution of Walkman, discman and mp5 players, I can't count the amount of wires I destroyed just having them in my pocket when walking or riding. Even high end woven wires and shit, end up failing due to mechanical stress. It is just entropy. I've had more headphones in my life than I can recall, but somehow BT headphones have lasted me 3 years, more than any of the cheap wired headphones of the past. Only my expensive sannheisers have lived longer and that's partially due to the fact they have detachable wires. So I can change them when they start to wear.