There seems to have been a couple posters with this complaint. I cannot for the life of me fathom why this is a deal-breaker. Can someone care to explain, or am I just missing some sarcasm?
Headphone jack on the bottom: Hold phone normally, rotate forearm and place in pocket. Everything's fine.
Headphone jack on top: Hold phone normally, rotate forearm and place in pocket. Break expensive earbud jack or worse, the female connector on the phone. Alternatively, have your muscles relearn how to place phone in pocket by first gripping the top half of the device between two fingers (greatly increasing the chance of dropping your expensive toy), allowing gravity to rotate the phone between your pincer grip, and placing in pocket.
Just tried it out, and I still prefer the headphone jack at the top.
Your scenario makes sense if you're trying to put it in a cargo pocket at the level of your knees, but rotating your forearm to put the phone in requires a very awkward shoulder shrug to get the phone high enough. That's for a pants pocket. It's even harder with a jacket pocket, which is my standard scenario.
To put a headphone-on-top phone into your pocket, lower your hand until the bottom of the phone is in your pocket. Then release your thumb or your pincer grip to push the phone into your pocket if it's a tight pocket. Otherwise just drop it in.
I'm not sure how human anatomy allows your scenario to happen. As I hold my phone in its normal grip, and lower my arm to the level of my jeans pocket, my wrist simply cannot bend enough to orient the phone correctly when the headphone is plugged into the top. I have to rotate my grip as I originally described.