It wasn't that Yan had any ill intentions toward Jiraiya. It was just that at certain critical moments, someone black-hearted was more reliable than a saint.
Was Jiraiya a saint?
He had some saintly tendencies, but not absolutely so. When it was time to deal a killing blow, he would not hesitate.
It was just that his overflowing sympathy occasionally became unbearable.
And he always came up with all sorts of bizarre ideas.
Once such thoughts took hold, forget the mission or any duty—he would toss it all aside first.
Jiraiya had that trait, and so did Naruto.
It allowed them to step forward and sacrifice themselves when necessary, never fearing death because of hardship or danger.
Likewise, it made them troublesome points of conflict.
So... to prevent that pervert from causing trouble, Yan chose to send a black-hearted fellow along as well.
With black-hearted Orochimaru watching him, even if Jiraiya had any ideas, he would have to keep them bottled up.
Because he knew exactly what kind of person Orochimaru was. If he slipped away, Orochimaru truly might capture Naruto for some research. Even if he had to face the consequences afterward, he would still dare to do it!
The purpose of sending Orochimaru to Kumogakure was simple. Besides satisfying his research needs, it was to have him keep an eye on Jiraiya.
With Orochimaru around, Jiraiya had to remain vigilant at all times. In that state, even if he wanted to cause trouble, he would lack the ability to do so.
"Boruto really is a lot like Naruto."
Holding Yan's hand, the two wandered aimlessly through the valley. Hinata, her face full of a blissful smile, suddenly brought up Boruto.
"He's Naruto's son. How could he not be like Naruto?"
Hinata's words made Yan laugh.
"But at times,