Leona has a few different lines about doing whatever it takes to win, but from what we have seen this may vary by situation: when it comes to spelldrive Leona says “Winning is everything,” and that victory in spelldrive is “the best treat of all,” but he seems ambivalent towards the concept of winning during Vargas Camp, helping out other groups with their tasks and saying, “Last I checked, this wasn’t a spelldrive game. No reason to get all competitive…At the end of the day, we’re all in this together.”
Despite a voice line of, “I’m not one to turn down a competition” he also turns down a competition that Rook proposes prior to Port Fest and another competition proposed during the event itself to see which of three different groups can sell the most churros.
In the middle of the day Leona has the three teams sell packs with all flavors together, resulting in all three selling out at the same time and compromising the competition entirely (Leona: “That stupid competition didn’t even matter”).
Leona also refuses the offer of a competition during New Year: Jack insists on enlisting Leona in a tako battle and when Leona asks why, Jack responds, “Because it’s a rare opportunity to go head-to-head with you! You’ve got good instincts, so you’ll probably pick up how to play pretty quick and put up a tough fight. And I wanna see how well I can hold my own against someone that good!”
Leona refuses anyway until both Jack and Ruggie pressure him together (“I’ll accept the ridiculous challenge if it’ll shut you guys up”), but Jack is disappointed when Leona’s tako is immediately taken out of the running. Ruggie observes, “That was some seriously bad luck! And Leona’s tako was a head higher than everyone else’s, so it took the whole brunt of the blow!,” and Leona responds, “…Oh yeah. Real unfortunate accident there.”
Leona then reveals that he intentionally threw the game. Jack and Floyd both demand a rematch, which Leona also refuses.
We have at least two examples of Leona maybe meeting his match in a competition: Idia in a game of chess (while it is not confirmed that their game ended in a draw, neither a winner nor a loser is ever stated) and Jack in arm wrestling.











