Pokemon: I Transmigrated Twice

The psychological issues of Pokémon are a fascinating subject.

In the anime, Ash's Sceptile once experienced heartbreak, causing it to be unable to use its moves for an extended period.

This incident could be considered one of the most infamous and unforgettable though such moments were rare.

Now, the same issue plagues the Umbreon.

If she doesn't overcome the hurdle in her heart, the damage will only worsen over time, eventually reaching a point of no return.

Finally, under Stephen's intense gaze, Umbreon shook her head with a determined yet hesitant look in her eyes.

This was her true inner voice.

And also the response Stephen had expected.

"Get a good night's sleep tonight. Starting tomorrow, we'll begin your personalized training plan."

Stephen didn't waste words and promised on the spot to help Umbreon break through her limits.

"Umbree!"

...

The Next Morning: Breakfast Time

"What? We're going to Alola?"

Will was stunned when he heard this news from Stephen. "Why? Is it because we've been training for so long that we need a break?"

The Alola region hasn't officially joined the Pokémon League yet, but it's renowned as the world's most famous vacation spot.

Its tropical beaches and the girls in bikinis are highly praised by travelers worldwide.

"They have some outstanding scientists there. Their research might help Umbreon break through its limitations."

Stephen glanced over at Umbreon, who appeared calm on the surface but whose unsettled gaze betrayed her lingering anxiety.

Her current state reminded Stephen of a nervous author starting a new novel—worried and fearful. Of course, even now, he's still scared.

"Let's all go together!" Will exclaimed eagerly. "The beach on Melemele Island in Alola is said to be the best in the world! And there are lots of bikini-clad beauties, hehe~"

As he said this, Will couldn't help but let out a mischievous chuckle.

Karen shot him a disgusted look, one that said, "You're garbage, and here's a panty-flash-level glare just to show how much of it you are."

Will smacked his lips and quickly explained he was just joking.

But it didn't stop his reputation from plummeting further in her mind.

"Vacation spot, huh? Do we have time to relax like this?" Karen asked, brushing her hand along the back of her Houndoom as it ate.

"Revenge is revenge, but life still has to go on," Stephen reminded her.

"Didn't you want to participate in the Indigo League and defeat Aldus in front of the whole world? You'll need at least six Pokémon for that, right? Alola's pleasant climate is perfect for all kinds of Pokémon. Who knows, you might find your next reliable partner there."

Stephen felt a bit drained at this point.

Not only did he have to provide psychological counseling for Pokémon, but now he had to do the same for people.

If Karen didn't adjust her personality, she might turn into a Second Sasuke in the Pokémon world.

"…Fine, I get it," Karen finally relented.

If there was anyone she still listened to, it was Stephen.

In her mind, Stephen had never been wrong about anything.

Seeing Karen agree, Stephen let out a sigh of relief.

If she had been too stubborn, he might've had to leave her.

After all, he wasn't like Ash, who could tolerate a disobedient Charizard for nearly 100 episodes.

If it were him? He'd release it and catch a more obedient Charmander to raise instead.

...

Cianwood Airport

"Hey, are you sure this is okay, Stephen?" Will whispered as they entered the terminal. He leaned toward Stephen and spoke in a low voice.

"It's fine for the two of us, but…"

Will gestured toward Karen and whispered, "If she registers her name, won't the League immediately know where she is?"

Even though the League's wanted posters featured masked photos of the three of them, it was no secret to the League that the Iron Masked Girl was Karen.

For some reason—maybe because Goodshow showed mercy, or perhaps Karen's father pulled some strings—the League hadn't publicized this information.

But if Karen bought a plane ticket, the League would undoubtedly be notified.

Wouldn't that also expose Stephen and Will's identities?

"No need to worry. We're taking a private jet," Stephen said, striding confidently past the ticket counters and heading straight for the VIP boarding area.

"Huh?"

Will froze for a moment before catching up.

Two minutes later, when he saw the small plane on the tarmac with Giovanni's face painted on it, he smacked his forehead.

Damn it, he'd forgotten that Stephen knew someone important.

"Welcome aboard Giovanni-sama's second private jet. I'm Yamato, assigned to serve the three of you."

As soon as they boarded and sat down, a young woman with orange hair, dressed as a flight attendant, greeted them with a smile and introduced herself.

"This flight from Cianwood City to Melemele Island in Alola will be serviced by myself and my partner, Kojiro—uh, I mean, Kosaburou."

"It's KOSABURŌ!!!" a man's voice roared from the cockpit.

Stephen casually tossed something to Yamato. "Here, give this to Uncle Giovanni for me."

Yamato hurried to catch it, her expression serious.

As an ordinary Team Rocket grunt, she didn't know much about Stephen's relationship with Giovanni.

But the fact that Giovanni personally assigned her and Kosaburo to this task showed how important these three were in Giovanni's eyes.

What Stephen handed over was a formula he had developed: APTX4869.

Yes, it was a De-Evolution serum.

He only gave it that name for his amusement.

After sitting down, Stephen glanced at Yamato for a moment.

Yamato and Kosaburo were a duo that appeared fairly often among Team Rocket members.

Although they had more funding and were slightly stronger than the comedic trio, they still never seemed to succeed in their plans during the episodes they appeared in.

Well… Maybe they succeeded a few times off-screen. The comedic trio probably just ruined those successes later.

What puzzled Stephen the most in his past life was that these two eventually left Team Rocket. One of them opened a café, and the other started a bakery.

"Hah, Giovanni is a good boss," Stephen chuckled to himself.

"Huh? Stephen-sama, do you need something?" Yamato asked, noticing his expression.

She had already decided to serve these three as attentively as possible. If she did well, maybe she'd get a promotion or a raise when she got back.

"No, nothing… Just keep up the good work. Uncle Giovanni is a great boss."

And Stephen wasn't just flattering Giovanni.

Giovanni had done plenty of shady things—Stephen wouldn't deny that.

But in worlds filled with terrible bosses, like Konoha's Elder Council in Naruto, Funny Valentine in JoJo's Bizarre Adventure, or the Five Elders in One Piece, Giovanni could easily rank among the top three Best Bosses.

As the leader of a criminal organization, he didn't kill or punish subordinates who wanted to leave. He let them go freely.

That kind of leniency was rare.