Pity him why?
Consider Star Trek IV from his point of view. His friend Gillian is high strung, upset at the release of the whales she loves. So Bob comes up with a daring plan - release them early, allowing the whales to avoid some stress and Gillian to make a clean break without a prolonged goodbye.
And what happens? She FREAKS OUT. She literally screams in his face, slaps his face, and storms off!
...and then she is never seen again. She just vanishes, completely. You can bet Bob filed a police report, but the police find nothing. It's as if she simply vanished into thin air.
And to cap it all, the damn whales vanished without trace the day they were released!
Bob HAS to be thinking "Christ... she killed herself. That's the only thing it can be, she killed herself and we never found the body. And it's because of me! Man, I didn't know she loved those whales THAT much!"
I think Bob probably blamed himself for that for the rest of his life. Major trauma, alcoholism, divorce, a life of failure for Bob Briggs.
Maybe he even killed himself out of remorse.
Meanwhile Gillian's living the high life in the 23rd century, flying around on science vessels and gallivanting with Kirk.
Poor Bob.
