We've watched pier runners before, but just out of coincidence as we hung out on our balcony right before the ship began the process of leaving. Never saw someone miss the ship though. It was amusing seeing them run, fast walk, regular walk, jog again, then slow walk onto the gangway. We never cheered or jeered at anyone, but just sort of smirked to ourselves.
I hope (confidently expect) that I never find myself in that situation. If we do a private tour, I always keep a close eye on the time and we have always returned to the dock plenty early.
If a party misses the ship out of sheer arrogance, inconsideration, or by drinking themselves into oblivion, I have little sympathy.