He's timid and always wants to run when danger appears.
Sometimes, he even makes up strange, unbelievable excuses—like claiming he has a rare illness that would cause instant death if he landed on a particular island.
In the original story, he was probably the one who suffered the most defeats in the group. Always seen as the "weakest," he frequently found himself clashing with powerful enemies. Yet despite his shortcomings, his heart brimmed with admiration and dreams of becoming a brave sea warrior.
In Leo's past life, there was a saying that circulated among fans of the sea:
"With the wind, you have rubber; against the wind, you have a sword; and in desperate moments, you must rely on the sniper."
Leo wondered if, this time, Usopp's performance would still live up to the version he remembered.
"Uh, hello, I'm Usopp, from this village."
Surprisingly, when drawn in by Leo's serious gaze, Usopp didn't start with one of his usual tall tales.
"Hey! Leo, did you find someone who can help us get a boat?"
Luffy's iconic laugh echoed from the distance as he sprinted up from the shoreline, excitement lighting up his face.
Nami followed closely behind, with Zoro lazily trailing after her. They had secured the ship and returned to regroup.
"Leo, where are my things?"
Before Nami even got close, her eager voice rang out. Her treasure—finally within reach—filled her with visible excitement.
Leo glanced at her, then casually waved his cane. A bundle flew into Nami's arms.
He had taken it earlier to lure her back to the ship. As promised, it also included an extra one million Berries.
Nami's eyes sparkled at the sight. She quickly squatted and began counting, her fingers flying over the crisp notes with a mix of joy and greed.
After dealing with Nami, Leo turned back to Luffy and pointed at Usopp.
"That's him. From what I've learned, Usopp should be very familiar with the woman in this village who builds ships."
Usopp took a few steps back, his eyes wary.
"Who the hell are you?!"
Being guessed so accurately shook him. The villagers here were just ordinary people. Only Kaya's family had the resources and skill to build a ship. While the strangers in front of him didn't look dangerous, he instinctively didn't want Kaya getting involved with them.
"I'm Luffy, the man who will become King of the Pirates!"
Luffy declared his dream without hesitation, beaming with pride.
"The Pirate King is awesome!!"
"Yeah! Even cooler than Usopp!"
"Uh-huh!"
The three carrot-headed kids nearby had already forgotten Leo's earlier intimidation. Now, they gazed at Luffy with stars in their eyes.
Usopp's expression shifted. He actually liked what Luffy had just said—he could borrow that line for one of his own tales next time he visited Kaya.
"So you really are pirates. But you came here just to find a ship, right?"
Usopp was quick to pinpoint the truth.
It had struck him as odd earlier. A pirate crew should have more than four members. And the ship they arrived on? Clearly a merchant vessel, even though it bore a pirate flag.
It was obvious these guys were rookies.
If they were that new to the sea… maybe the villagers could fight them off?
Usopp's mind worked fast. The only problem was the mysterious strength of Leo and the others.
"Yes. And we're still looking for new crewmates. Do you know where there's a shipbuilding company nearby?"
Leo responded when no one else did—Nami was still counting money, Luffy was laughing with his arms crossed, and Zoro was half-asleep under a tree.
"Hahaha! Then you've found the right person! There's no ship that I, the great Captain Usopp, cannot locate on these seas! Back in the day, I led 8,000 men across the Grand Line! We sailed through typhoons and…"
Usopp's voice boomed with confidence as he launched into one of his wild stories.
The three carrot-heads were clearly used to this. Their eyes sparkled with admiration as they hung on every word.
Even Luffy was impressed, his grin growing wider with every sentence.
"How about that, huh? Pretty amazing, right? Didn't you say you're looking for a partner?"
Usopp asked with satisfaction, still riding the high of his storytelling.
He was starting to like Luffy. Other than Kaya, this was the first person his age who genuinely seemed to believe his stories.
"Do you know someone who's a good fit?"
Luffy asked seriously, his expression sobering. He was earnest about recruiting only the right people.
"I can be your captain!!"
Usopp said it with dramatic flair.
"NO NEED!!"
Luffy, Leo, Nami, and Zoro all shouted in unison—snapping out of their moods and responding before they could stop themselves.
Usopp was stunned into silence. After awkwardly clearing his throat, he waved them to follow.
"…Then please follow me. I'll go make arrangements about the ship."
He disappeared down a path toward the village.
But Leo had a good idea where he was headed: Kaya's mansion.
He could tell Usopp wasn't just helping for fun. Most likely, he was doing all of this for that girl.
"Leo, that guy is such a braggart," Nami said lightly, walking beside him and flipping through her Berries with a smug grin.
"No! Captain Usopp is not a braggart!"
Before Leo could reply, the three little carrot-heads jumped in to defend their hero. They started excitedly talking about how Usopp always went to cheer up a sick girl who had lost her parents.
Nami paused mid-count. She hadn't expected such an explanation and felt a slight change in her opinion of the so-called liar.
"So that's why…" she muttered.
"Alright then! Let's go meet this Kaya too!"
Luffy declared with enthusiasm. He wasn't entirely sure why, but from the moment he saw Usopp, he'd felt a strong sense of familiarity.
Leo nodded in agreement. In his heart, he didn't want to disrupt the original story too much. If people who were supposed to be part of the journey started disappearing, it might change everything.
After a short rest, the group set out. Led by the energetic carrot-head trio, they made their way toward Kaya's mansion.
"Hahahaha… And then what happened with the goldfish?"
Kaya asked, her eyes twinkling with amusement.
"I chopped it into pieces and sent it to Lilliput! We still haven't finished eating it!"
Usopp puffed up with pride as he finished the story, delighted by Kaya's laughter.
But before the moment could continue, a sharp voice interrupted.
A tall, thin man in a black suit stepped out. His round-framed glasses glinted in the sunlight, and he carried an air of cold precision.
It was Kaya's butler.
He didn't even glance at Usopp as he addressed Kaya directly.
"Miss, I must remind you for the sake of your health… I advised you not to speak to this liar."