It's a tie between Jake and Tobias, but I'm going to go with Tobias. Yeah, he lost everything. It sucks, he's heartbroken. How much would Rachel have liked for him to spend the rest of his life moping about it, though? I mean, she would have kicked his feathery butt (excuse the marco-ism). Also, he gave up on what he potentially could have had. Like his mother, who he finally found.