Woop Slap has been the mayor of Luffy's hometown for over a decade. He was actually the first person to defend Luffy when he got into it with Higuma as a kid—he even begged Higuma to spare the boy's life. That said, he's never been happy about Luffy's pirate ambitions, viewing them as a disgrace to the village. He's called it Luffy's "destiny" before, though he seemed to be asking more than stating.
Even now, Woop Slap remains conflicted about the whole thing. He disapproves of Luffy's infamy and was visibly disappointed when the villagers started drinking to celebrate one of his bounties. But his concern for Luffy's actual wellbeing is genuine. His constant criticism seems to come more from his position as an authority figure—the idea of Luffy and his father openly defying the World Government just strikes him as reckless. He's even said Luffy's a better choice than the "freaks" who sailed with him, suggesting he doesn't entirely disapprove of his former neighbor as a person.
He talks to Makino pretty regularly about Luffy, probably because she's one of the few people in town willing to actually listen to his complaints.
Woop Slap knows the Garp family well enough to have his own opinions about them. He thinks all three generations are crazy—Garp, Dragon, and Luffy included. He's also wondered whether Dadan ever found out about the Enies Lobby incident.
Content compiled by AnimeList.moe from publicly available sources.
