The Young Chief was not surprised when Young Master Red Lion and Ojou announced their betrothal. Or rather, he wasn't surprised when Shin announced the betrothal while Ojou threatened to kill him. In fact, Kyou noticed that none of the Kuroda-gumi seemed surprised; a nice contrast to the reactions of the Tanukibara-gumi and the Uma-no-o gumi, who at the formal announcement responded unfavorably. Rather, the Kuroda clan laughed and teased Ojou about the "next generation". So no, Ooshima Kyou was not surprised at all.

The entire household knew that Ojou possessed a liking for smart men, it was why the lawyer stuck around for so long. Like Shinohara-san, Shin was incredibly smart; but unlike Shinohara sensei, Shin possessed the cunning that the gokudo admired. Kyou recognized that on his first encounter with the Young Master-before he was the Young Master, when he was just Sawada Shin- in what became known as "the Kuroda Family theater". As Kyou pretended to beat this precious Ojou, he caught the gleam in the redhead's eye. At the time he brushed it off, too distraught over his actions toward Ojou, but later when he reflected on the moment over a cigarette, Kyou realized the boy knew the production was false and had tucked the information away for further use. Kyou smirked, then slowly inhaled, exhaled. 'Smart kid', he thought, 'We could use a few young ones like that.'

It was on their second encounter that Kyou learned of Shin's honor. When Kyou first joined the underworld, everyone adhered to the unspoken rules of the gokudo. After all, they were all just men trying to make it in a MAN's world. Unfortunately, as he grew older, people began to disregard the rules, choosing power and violence over honor. At one point, it would have been dishonorable to attack an unarmed man's back; now it was commonplace. It was becoming rarer to see the young one's respond to the code. So, when he heard a voice telling him to watch his back, he expected an aniki or one of his brothers. Instead, he got a redhead gaki covering him. He had no affiliations or kinship with this brat, but they fought side by side as brothers and then entered a teasing argument like old friends. This redhead kid had honor, and followed the code. Kyou could respect that, after all, he was a man of honor himself.

And despite having honor, Young Master Red Lion was not prideful. No, he was humble and courageous. It takes courage to run barehanded into a fight, but it takes a deeper courage and humility to bow your head to another and ask for help or forgiveness. Some might see it as weakness, but Kyou respected it. So, when Sawada Shin humbled himself before his father on bowed knees, and the forcefully explained himself, Kyou's heart almost burst. This boy had the makings of a man: intelligence, honor, courage, humility, cunning. As he said back then, "Give him two to three years and he'll become a damn good yakuza, you know!"

But it didn't take a few years. In a few months, he challenged the lawyer, propositioned the boss, and confessed his intentions to Ojou. In a few months, Shin was already a man's MAN in Kyou's eyes.

Even more, Shin was incredibly loyal. Minoru and Tetsu once told Kyou that Shin played decoy for Ojou, willing to do anything to help her take down Nekomata's drug ring. Then, weeks later when Kyou had been released from jail, he ran head first into the Nekomata warehouse with no backup to save Ojou when she was sick. When the gumi arrived, Shin had already defeated the large octopus head. Beaten and barely able to walk, Shin still stood between Ojou and problem child Kudou, ready to die for her sake. Years later, when the Young Master Red Lion had finally joined the Kuroda group, Kyou and "Shin-chan" would tell each other stories over sake. Eventually, Kyou would begin to see a trend in Shin's stories and complaints. One of the Shirokin brats would get in trouble, or one of the gumi would find themselves in a tough spot, and Shin would run after them, willing to fight for his brothers. More likely though, Ojou would find herself in a spot of trouble with her students or the underworld, and Shin would chase after her to fix it. Shin was always chasing Ojou-in love, in trouble, and into a fight or scheme. Always behind her, giving advice and help, but always there. So when the Young Master would complain of Ojou's antics, the Young Chief would just grin into his glass and take another sip of sake, because that's what you get for being so loyal.

Of course, without his help Ojou would have never even considered Shin. If not for him, Shin would have had to wait a hundred years before Ojou would consider him a man. Luckily for the Young Master, he had taken a liking for the brat and begun routing for him. The result: a fundoshi and 99 years taken off of the Young Master's sentence.

Most of all, Young Master Red Lion was strong. Physically; as Shin had advanced in the gumi he had gained strength, able to take down multiple opponents, and even go head to head with Ojou on occasion. Morally; Shin upheld the code, protecting those under his care or whomever needed it. He was steadfast, persisting after Ojou for years in order for her to see him fully as a true man. He was forceful, able to command the courtroom and the battlefield. To Kyou, Shin would never fully reach the Boss's level, but he was rapidly approaching the platform.

The added bonus of Shin's leadership skills made Kyou grin with glee. Like the Boss, Shin took a back seat approach. As he did with his high school class, Shin allowed the gumi to do what they pleased, and even participated in some of their endeavors, only stepping in when trouble occurred or when someone or something went too far. He allowed the men to stack their beaten opponents in packs, he let them run out of the compound on an unnecessary raid, he let them threaten Ojou's students. Even so, he stayed true to the code and punished those who broke it. He put the safety of the clan before all else, while allowing the men to act like the yakuza they were. He inspired fear and trust, earning the loyalty of the men who followed him.

Over all, Shin-chan—soon to be Yondaime—was a man's MAN. The type everyone in the gokudo aspired to be. From the very beginning—through the raids, shootings, kidnappings, legal battles—and through all the crazy adventures of the Kuroda clan, Shin had remained true to himself and the yakuza way of life. In the end, the red-haired gaki who chased after their precious Ojou had become the only man worthy of standing at her side. So no, it was no surprise at all, because Kyou always knew Shin had all the makings of a yakuza.