After listening to the chat between Leafy and Sam, it has become clear to me that Sam feels genuine empathy for Ian. I mean, no one would describe him as a "not bad" boxer without feeling some sort of empathy towards him, because like, the dude is fucking terrible. Everyone saw this, everyone knows.
The funniest part of all of this is that, really, it seems like Sam wants the best for Ian. Seriously. He genuinely would love to see him pull himself up, or at least that's the impression I get from everything he's said about the guy. All the while, Ian and his master Anisa seethe at the very mention of Sam's name. It would be sad, if I weren't laughing at the Johmas' continuous failures while blaming that darn evil Neo-Nazi Samuel Hyde.