Work Header

Road to Riches

Work Text:

Jessie was, admittedly, disappointed. It was early summertime, which usually had the best weather for traveling and tracking the Pokemon trainers they had grown so accustomed to over the years. She was sitting at a bar, however, not even bothering to dress in her Team Rocket gear. She was already feeling a bit buzzed, and she didn’t have anyone to enjoy it with. So typical, she thought to herself.

A few weeks before, they had experienced a particularly bad defeat and received a “suggestion” from the boss that they split up and try to succeed individually. Giovanni understandably didn’t know what to do with them anymore and was obviously trying a new approach to see if it would change anything. It backfired immediately, however, because James had gone back to his family and Meowth had returned to Christopher’s ramen shop. The cat had insisted that if they couldn’t work together, he didn’t want to do it alone, and James had wholeheartedly agreed. Jessie, however, was a bit shell-shocked during the meeting and remained uncharacteristically quiet. While she had dreams of becoming a top coordinator, she still felt a tug of longing to be a part of something and decided that if she couldn’t be with her best friends, she at least wanted to keep her current job. Even when they had parted shortly after, she was still completely stunned by the situation and did not get nearly as emotional as her two friends did. They both told her they would see her again soon, but she knew they didn’t mean that.

This was not the first time someone had left Jessie behind. Old boyfriends, her old foster families, her mom... it didn’t even surprise her anymore. Since she left James and Meowth, she had been casually ignoring any new missions from her superiors and opted to relax instead with some martinis near the beach. She deserved it, after all.

Jessie was starting to notice some drawbacks, however. She was used to constantly being around people. Jessie, James and Meowth had rarely separated before, and while it felt like a relief at first to finally get some alone time, it felt completely unnatural by the second night. In her hotel room, she would wake up in the middle of the night after a nightmare expecting to see her partners fast asleep, something that had always brought her comfort. When there was nothing but quiet darkness, that’s when the sheer panic set in. Jessie liked to think that being independent was thrilling, but it was truly the exact opposite.

So that’s where the bar came in. This bar had quickly become a favorite of hers, and she had come here several times throughout the past couple of weeks. She appreciated how hard it was trying to be a tourist trap with all of its tacky, surf-themed decorations and noted that it was definitely working for them because she already felt like a regular after such a short time. But then, there was also another reason she kept coming back.

There was a bartender who usually worked weeknights that she enjoyed chatting with. Her name was Amelia, and she knew how much Jessie enjoyed her pineapple martinis. She also thought that Wobbuffet was adorable and rewarded his charming behavior with a bowl of Pokemon food every time, much to Jessie’s confusion but also something else she appreciated. They would usually talk about small things, like whatever was on the TV at the bar or crazy customers Amelia had served. Jessie would share stories of her travels without letting on that she was a part of an international criminal organization, leading Amelia to believe she was just an eccentric explorer. Which wasn’t entirely untrue, Jessie decided.

There was also the fact that Amelia bore an uncanny resemblance to someone, something Jessie was struggling to admit to herself. Amelia had light blue hair (almost lavender) that was shoulder length and usually pulled back. She had green eyes, darker than ones she was used to but still lit up when she was amused by something on TV or a snarky comment Jessie had made. The small exchanges she had with Amelia were both comforting and painful at the same time for reasons Jessie did not want to dwell on.

At this point, Jessie had already downed another martini and was feeling tipsier than before. She knew that while Amelia provided some of the dearly missed conversation she had with her teammates, there was still a sense of longing she couldn’t quite pinpoint when Jessie was around her. Heck, even when Amelia talked about her cat it made her sad. So pathetic, Jessie thought to herself.

Jessie felt her phone buzz in her pocket. She took it out and looked at the screen, and felt her breath catch for a moment when she saw what it was. It was a text from James, and from the preview, it looked like a picture of him. Jessie opened the text and couldn't help but smile.

It was a picture of him frowning by the pool with his parents in the background, laughing and drinking cocktails. There was no sign of Jessebelle, but Jessie assumed she was nearby.

Jessie texted back.

Jessie: where's spawn of satan?

James: she's on vacation with her own parents thank god

Jessie felt slightly relieved that her friend didn't have to deal with his awful fiancée. She was about to respond before James sent another text.

James: so how’s life in team rocket?

She thought about her response before taking a picture of herself looking bored by the bar. She sent it to James.

James: are you on a mission in a bar

Jessie: yeah sure

James: lol enjoy yourself, you deserve it

Jessie smiled, but also felt a pang of sadness as she realized how much she missed her friend.

Jessie: can i call you later? and meowth too… i have so much to tell you guys about what they have me doing now

James: please, i would love to have a conversation with people who don’t bring up jessebelle every five minutes

James: plus i miss you guys :(

Now that pang of sadness was more like a brick in her chest, weighing her down and reminding her of this friendship she could have easily lost. She was grateful that he ended up reaching out to her because every time she tried, she couldn’t bring herself to do it. It wasn’t a huge surprise that James still wanted to keep in contact after not being apart from each other for years, but it was also a relief.

Jessie: i miss you guys too, i’ll talk to you later

Jessie felt almost strange sending that to him. The words felt foreign and unused in her vocabulary, now only reserved for her teammates she was newly separated from. That feeling of longing was gnawing at her, that desire to continue the routine she had fallen into for years. Traveling around with her two friends as they try to keep up with the twerps was draining, sure, but it was also the best time of her life. She sighed before taking another sip of her drink. This was the new beginning of a new era in her life, and she wasn’t entirely sure if she was ready for it.


Talking to her longtime friends over the phone was different, but not unwelcome. Jessie's phone had rung around 7:30 PM that night. Praying it wasn't the boss when she answered, she was relieved when she heard a familiar voice.

"Hello? Jess?"

"It's me, James," she said, trying to sound casual but ultimately failing. "How are you?"

"I'm still in a close vicinity to my parents," he told her, "So... bad."

Jessie laughed. "Sorry to hear. How do we add Meowth into this phone call? I don’t have the ramen shop’s number…”

The two discovered the joys of trying to conduct a group phone call before finally getting their other friend on the line.

“Meowth? Are you there?”

“It’s me, Jimmy! Is Jess there?”

“I’m here too, Meowth.”

“How ‘bout the blue guy?”

At the mention of his existence, Wobbuffet came out of his Pokeball and announced himself. James and Meowth heard over the phone and laughed.

“So where are you guys? What’s the news?”

“I’m in Alola,” Jessie told him, and then more grudgingly, “James is still with his parents.”

“Yeesh,” the cat said, obviously knowing what that entailed. “That’s rough, Jim.”

“”Rough’ is putting it lightly,” James said, sighing. “You guys don’t know how happy I am to be talking to you right now.”

“I’m glad to be talkin’ to you guys, too. The shop is non-stop busy and I feel like I’m always breakin’ a claw to try to keep things together!”

“How is that, anyway?” Jessie asked her friend. “Still serving hundreds of bowls a day?”

“You bet! Besides all the hassle, it’s a rewarding gig,” Meowth told them, “It’s nice puttin’ smiles on peoples’ faces with food that you made ‘em. Reminds me of the times when we did the same and were rollin’ in dough… at least until we blew it all.”

The three reminisced for a couple of hours. Comfortable lulls in conversation happened every once in a while, and Jessie ended up falling asleep during one of Meowth's many stories about his now solo adventure.

She woke up the next morning feeling as though James and Meowth should be there after having just talked to them before falling asleep. Jessie felt the uncomfortable absence come crashing back before sighing and forcing herself to get up for the day.

Figuring it had been long enough, Jessie decided that she would partake in a new mission. She didn’t have the twerps to track anymore, and she wasn’t feeling very inspired to do anything else. After talking to a superior, she got a mission to “keep an eye” on a specific tourist in her area. She would receive more information shortly.

Jessie sighed. God, this was mind-numbing, she thought to herself. Normally she would have her friends to pass the time with, talking about nothing or maybe even trying to think of preemptive plans. Now, all she had was her own thoughts. She suddenly realized that this didn’t have to be the case.

Jessie: just got a new mission

A few minutes passed before she got a reply.

James: exciting!! what is it

Jessie: trailing a tourist? pretty lame, if you ask me

James: interesting... and not worthy of your talents lol

Jessie: right?

Jessie then got the text from her supervisor about the “client.” She stared at her screen, unblinking for several moments before she could really process who this person was. In the text was a picture of someone who she hadn’t been reminded of until very recently.


Jessie: so i have an update about the mission…


At the very least, Jessie was happy she could still wear her own clothes. She had gotten instructions to blend in, and her touristy get-up fit in perfectly. On the other hand, this mission was more boring than she could possibly imagine.

All Jessebelle did was shop, go to fancy restaurants with her parents, and relax on the beach. She was grateful for the latter because it meant she could also relax on the beach, but the other rich-person activities she could have done without. The only savior she had was her ability to text James and update him on this ridiculous situation.

Jessie: she just bought ANOTHER handbag, how many bags does one person need??

James: don’t tell me you wouldn’t do the same thing if you were loaded

Jessie thought for a moment. She did have dreams of huge shopping sprees and had participated in one or two in her lifetime, but she liked to think that she would branch out more.

Jessie: i would be smarter with my money, of course. my closet would be full of beautiful dresses and jewelry to accentuate my already immaculate features

James: of course, i would expect nothing less from you. i’d also have the best clothes, and the rarest bottlecaps i can get my hands on

Jessie smiled as she remembered the stakes her partner was willing to go to for his bottlecaps. She then got another text from him.

James: but what else would you do if you had money? i would be far away from here, as you probably could have guessed

Jessie thought for a moment about his question. She liked the area she was currently in, sure. It was always warm and she felt like she was constantly on vacation. Her hotel room could be better, but she expected that from Team Rocket. There were really only two things missing, and having money definitely wouldn’t hurt the situation.

Jessie: i’d love one of these mansions on the beach i keep seeing. spawn of satan and mr and mrs satan are all staying in one

James: i’m not surprised

Jessie: but you guys would be here with me, of course. we could live out our wildest dreams while drinking martinis and laughing at tourists attempting to surf

James: lol i wouldn’t mind that at all, that sounds amazing

Jessie smiled at this, wishing it could be their reality. If money weren’t an issue, the world would be eating out of the palm of her hand. She could participate in any contest she wanted to anywhere in the world, and then come home to her amazing beach house and best friends. She sighed as thought about how far away she was from obtaining this dream.

Jessie continued tracking Jessebelle throughout the day, following her from a distance as she purchased an impressive number of items before attending some boring fundraiser for Vileplumes. Jessie was able to easily crash the event disguised as a fancy donor to the cause. She kept to herself at the luxurious food table and watched Jessebelle from afar as she schmoozed with other rich partygoers. Nothing struck her as odd until a seemingly average man escorted her from the dance floor and into the hallway. Jessie followed behind, figuring she could claim she was trying to find the bathroom if she got caught. The two didn’t seem to notice her presence, luckily. She prayed that Wobbuffet would stay in his Pokeball.

Jessebelle and the man walked to the end of the corridor talking in hushed but serious tones. Jessie hid behind a large sculpture in the hallway and was able to catch bits and pieces of their conversation.

“I’ll have the money transferred to you tomorrow,” she heard Jessebelle tell the man in that frighteningly sweet voice of hers, “I need that green Vileplume ASAP to bring to my Jamesy.”

Jessie cringed at the nickname, but also determined that this was the reason Team Rocket wanted her to trail Jessebelle. There was clearly some intel about Jessebelle looking into the rare Pokemon market, and one of the higher ups thought it was important enough to keep an eye on her. Of all people, it was an insane coincidence that Jessie was the one chosen to do this. She did figure, however, that they needed a lone agent to complete this covert mission and that the usual Team Rocket duo or trio would be overdoing it. Jessie was also known for how well she worked independently (at least until she found the other two, of course).

After taking out her phone, she texted her superior with the newfound information. No more than two minutes later did she receive instructions to “stop the trade at all costs.” She was a little taken aback by how urgent the message sounded, but was still up for the challenge. Finally, her talents were being utilized correctly.


Jessie looked in the mirror after getting dressed. God, I look ridiculous, she thought to herself with a frown.

Her hair fell from her shoulders in large curls, and she wore a conservative red dress with obnoxious green earrings. She had done this once before in an attempt to get back James’ precious treasure chest, and no one had seen through her disguise. She figured they weren’t identical enough for this to be a foolproof plan, but hopefully the person she was about to interact with didn’t know Jessebelle’s features well enough to be able to tell there was anything off.

Her plan was simple. Jessie had been able to determine where the meeting would take place from the conversation at the fundraiser. She had already led Jessebelle on a goose chase by leaving her a message from the man to meet her in the next town over, and then trailed her for a bit to confirm that she had truly gone. She now had a short window of time in which she could get to the docks disguised as Jessebelle and cancel the trade with the man. Of course the sketchy meeting is happening at the docks, Jessie thought to herself with an eye roll.

Thinking it would be funny, she took a picture of herself dressed as Jessebelle and sent it to James.

James: ????? jessebelle?????

Jessie: only temporarily haha

James: the resemblance is uncanny

James: my mom saw the pic of you on my screen and actually thought it was jessebelle

Jessie was surprised by this, and a little worried about what the implications were of James supposedly keeping contact with Jessebelle.

Jessie: oh god, what did she say??

James: she just kept going on about how great it is that i’m talking to my “future wife” without letting me get a word in edgewise

James: and now i think she’s in the other room booking the wedding

Jessie cringed at this, and also felt a little bad because it was her fault for sending the picture.

Jessie: i’m sorry, i had no idea that would happen

James: it’s alright, it’s not your fault! my parents have NOT stopped talking her up lately and how great of a wife she is going to be

Jessie: she’s pulling something illegal to get you a shiny vileplume, that’s certainly something

Jessie: i would definitely take it and run tho

James: why are you dressed as her, anyway? is this why they chose you for this mission?

This hadn’t occurred to Jessie before, but James could be right. She didn’t really think her superiors were clever enough to think this far ahead, but they’ve certainly surprised her before. Jessie sighed as she got up to leave for the beach, phone still in hand.

Jessie: i have to meet with this vileplume man dressed as her to stop the trade

James: well i’m sure it’ll work. not only do you look eerily like her, but you are also an amazing actress!

Jessie smiled at her phone, feeling smug because of course he was right but also strange because of a funny feeling she had in her chest. She couldn’t determine whether she was nervous about the mission or if something else was bothering her. James sent another text that snapped her out of her thoughts.

James: ....jess, this does give me an idea

Jessie: what is it??

James: do you think you would be able to keep jessebelle distracted for a while? like several days?

Jessie thought for a minute. Right now, she was speed-walking to the beach in order to meet this strange man on time. She supposed that given more time to think, she would be able to come up with a plan to get Jessebelle to leave for a longer period of time. Heck, she could tell her the Vileplume was somewhere in the Sinnoh mountains and she’d have to go there and get it herself.

Jessie: definitely, why?

James: i think that your disguise just might be good enough to fool my parents in person

Jessie stopped walking to confirm she had read that correctly.

Jessie: are you sure?? while i do have impeccable acting skills, they do actually know the beast. i don’t know if they’ll actually believe i’m jessebelle

James: i really think you can pull it off. if they think anything’s fishy, we can say you’re coming down with something

James: if we can do this, jess.... i could get my inheritance, and we could be loaded

James: you can get all the dresses and jewelry you want (and the thousands of handbags i know you secretly want) and we could have the best life in the beach house of your dreams

James: sorry for all these texts, it’s just.... the whole reason i came here of all places was so i could try to get my inheritance, and i think this is something we should consider trying

Jessie read these texts, but needed some time to actually think about what they contained. Jessie had now reached the beach, and saw the man standing on the docks ahead of her. She told James she would answer him after this meeting was done, and braced herself to lie her ass off.

After approaching him, she curtsied and spoke in a sickeningly pleasant tone to the man, explaining she had made a mistake in trying to buy this rare Vileplume and that the deal was off. The green Vileplume stood hiding behind the man’s leg, keeping to itself. The man seemed confused by her turning down the trade, clearly remembering Jessebelle’s desperation the night before, but was otherwise unaffected by this ordeal. She made sure to add that he should never try to contact her again, and anyone who tries to under her name should not be taken seriously. He shrugged and walked off of the docks, disappearing into the darkness of the beach. Vileplume stared at her for a moment with a puzzled look on its face before following the man. Jessie let out a deep breath she didn’t know she was holding before telling her superior that her mission was complete. She also made another decision that she hoped was the right one.

Jessie: alright, the great actress will assist you


Jessie, as promised, had gotten Jessebelle to leave for Sinnoh the next morning. After arriving at the supposed location the day before and not finding the man there, Jessebelle had frantically contacted him to try and figure out what was happening. Coincidentally, the contact information for this man that Jessebelle had was actually Jessie’s burner phone, and she told her that a family emergency had occurred in Sinnoh and that she should meet him there if she still wanted the Vileplume. Jessie watched as Jessebelle boarded a plane, pleased with herself about how flawlessly her plan had worked. She soon boarded her bus to get to James’ house.

Jessie haphazardly threw her disguise on at a rest stop on the way. Sending another picture of herself as Jessebelle to James, she hoped that it would be good enough to fool his parents.

James: you look great!

James: well, not great but... like jessebelle

Jessie smirked as she got back on the bus, putting her phone away so she could think before getting to James’ house. She hadn’t seen him in so long, and was a little nervous about it. It felt silly to be nervous about seeing James, but they went from spending everyday together to no days at all. Talking to him on the phone also made things feel different, because they were choosing to talk to each other rather than having to work together. Not that it hadn’t been great before, but this was just... better?

She felt odd thinking that. Things weren’t better, obviously. She had limited contact with both of her friends, mostly Meowth because he physically could not text them and only had so much time to speak over the phone, and Jessie missed him more than anyone. She at least had the ability to talk to James whenever she wanted (and when he was available), and being away from him had made her realize how much she truly enjoyed talking to him and sharing her thoughts with him throughout the day. She couldn’t imagine a life without him in it, and those couple of weeks where she didn’t hear from him felt unbelievably wrong. Jessie had had the bar to spend time at, Amelia to talk to, and even the beautiful beach to enjoy, but she had wanted him to be there to enjoy it all with her.

Jessie sighed. Her chest felt light and heavy at the same time, a feeling she recognized well. Of course this would happen after they were separated, possibly forever if this plan doesn’t work out. She also considered that maybe he wouldn’t return these feelings and that this was all on her end. He would be missing out, of course, but she also figured James was as oblivious as he was charming.

The bus let her off fairly close to James’ driveway, but she could still barely see his mansion in the distance.

Jessie: i’m at the end of your private road

James: it’s the driveway but....yeah

Jessie walked for about ten minutes before arriving at the front door. She took a deep breath before knocking on the door, praying that James would be the one to open it. One of the big doors slowly creeped open before she saw James’ butler standing there diligently.

“Why, Lady Jessebelle! Marvelous to see you! Please come in, Master James is around here somewhere, let me-“

“Jessebelle!” She heard a familiar voice say as she entered the room. It felt strange seeing him in a suit and not the Team Rocket uniform, and she figured it was his parent’s doing. Despite the falseness in his greeting, James’s smile was genuine as he walked up to her and hugged her tightly. She hugged him back, figuring it was alright to do disguised as Jessebelle if he was initiating it. He smelled like expensive cologne, and she smiled into his neck knowing he was definitely enjoying all the quirks of being wealthy while he still could. He pulled away from her, but still kept his hands on her arms as he discreetly kissed her cheek, something that made Jessie freeze as she tried to process it while keeping her act going. “Jessebelle” smiled weakly before curtsying, something that Jessie had noticed a lot of while trailing the woman, before allowing James to kiss her hand in a gentlemanly fashion.

“The Masters will be so pleased to know your fiancée is here, Master James! Excuse me, I’ll let them know of Lady Jessebelle’s arrival.”

His butler left the room, and Jessie felt her shoulders relax. She looked at James, who laughed softly before taking her hand and leading her into a different room. This room was the true living room, Jessie assumed, as the last room was only the “foyer.” Mansions are ridiculous, Jessie thought to herself.

“I’m so glad you’re here,” James told her, now sitting on the golden-plated couch. Jessie sat down and crossed her legs, trying her best to appear “proper” even when no one else was there besides James.

“I really hope this works,” she said quietly while trying to read James’ face. He seemed nervous, but there was also a light in his eye that made that feeling in her chest flutter.

“I have faith in your acting abilities,” he told her, reaching forward to play with her curls, “And the fact that you look almost exactly like her doesn’t hurt, either.”

Jessie laughed, mostly because of the nerves that ensued while he was in her personal space. They had lived in each other’s personal space for god knows how long, but now it felt electrified as his hand stroked her hair and his other hand rested casually on top of hers.

“I missed you, James,” she said softly, trying hard not to make eye contact, “I’m so glad we still get to talk, but-“

“Ah, Master James!” They heard his butler exclaim, and immediately pulled away from each other as if they had done something wrong. They both quickly realized that that probably looked more suspicious than the alternative, but the butler didn’t seem to notice.

“The Masters are just this way, if you’ll follow me.”

Sighing, Jessie allowed James to take her hand again as his butler lead them down the corridor. She looked around at all the tall, lavish paintings as canvas images of James’ family members looked down at her. She took note of all the rare-looking artifacts they passed on the way, and she gulped as she realized that they were trying to scam truly powerful and influential people. She was comforted by James’ confidence, however, as well as his gentle grip on her hand.

They stopped in front of two large oak doors, and the butler held one open for them. James let “Jessebelle” step in front of him with a smirk before walking in behind her.

James’s father sat at his desk, his mother standing in front of it. They both gasped when they saw the woman before them, clearly unable to believe their eyes.

“Why, it really is Jessebelle!” James’ mother exclaimed, hugging her as Jessie tried to cover her face as much as possible with her fan, “I am so happy for the two of you!”

“It’s so nice to see you both!” Jessie told them in her fakest, most pleasant tone, “I’m so excited to marry your son and get...our lives started together!”

Jessie winced as she felt herself almost slip up. The two didn’t seem to notice, however, as they still had comically large smiles on their faces.

“The wedding will be next week, don’t you worry! Everything’s been sorted out,” his mother told her reassuringly. Jessie was shocked by how fast this woman worked, but supposed she had been dreaming of this wedding for years and had it planned way ahead of time.

“That’s wonderful news!” James chimed in, but Jessie could hear the slight edge in his voice. He was most likely worried about keeping the real Jessebelle away for that long. “Is there any way we could push it up a little bit? Like to this weekend?”

“Why, James!” His father exclaimed, clearly surprised, “I’ve never seen you so eager to get married before! All that time on the road has changed you.”

“Yeah, it’s certainly made me realize what I want in life,” James said, sneaking a glance at Jessie. She smirked in response.

“Please, let’s move to the living room!” His mother told them, “We’ll have tea and catch up.”

“That sounds wonderful!” Jessie said through gritted teeth behind her fan.

James placed his hand on Jessie’s back as they walked out of the room and whispered, “You’re doing great,” in her ear, making her shiver. She smiled at him in response as they made their way to the living room, wondering just how far they could take this.

They were all seated now, sitting on elegant couches as the butler served them some sort of fancy tea Jessie had never had before. She was careful to mirror the actions of the more “proper” people around her so as not to cause suspicion.

“So, Jessie,” his mother said after taking a sip of tea, “How long have you been pretending to be Jessebelle?”

Jessie immediately almost spit her tea everywhere. She carefully put the cup back on the table and tried to keep her cool. She felt James tense up next to her.

“Why, I don’t know what you mean-“

She was cut off by a loud, distinct laughter from around the corner. Of course.

She entered the room with a terrifying grace that only the real Jessebelle could muster. She would be innocent-looking, Jessie decided, if it weren’t for that consistent plotting look in her green eyes.

“Why, thank you for bringing my Jamesy to me, Miss Jessie,” Jessebelle told her, “But that was mighty rude of you to cancel my business for me.”

“None of that was real, was it?” Jessie said, almost to herself as the pieces came together in her mind. “It was all a setup... Team Rocket’s not even safe from the likes of you!”

“Mr. Giovanni was happy to accept my offer, Miss Jessie,” she said, sounding impossibly polite, “He was happy to send you on a wild goose chase for a few measly millions.”

“But you already had James here, why-“

“Actually, darlin’,” Jessebelle said, now standing in front of Jessie, “You were the one I needed this time.”

Jessie’s stomach dropped as she tried to process her words.

“But why?”

“I need a favor from you,” the socialite told her in a casually sweet tone that would sound normal out of context, “And it’s a lot to ask, I know.”

“What is it?”

Jessebelle wore a mockingly sad expression, something that made Jessie’s stomach turn.

“I need you and the cat to keep away from Jamesy so we can start our new lives together.”

Jessie was shocked. Why her? Why did she jump through so many hoops just to trick Jessie into coming here and ask her for a favor? Why the hell would she do her this favor, of all things-

“Of course, there would be money involved.”

Jessie’s ears perked up at this.

“How much money are we talking?”

“Millions, Miss Jessie. Anything you want! You and that mangey cat can have it all!”

The gears in her mind were turning quickly. The idea of millions of dollars obviously appealed to her, and it was tempting to take it and leave. If I can somehow get the money and James the hell away from this place, however, that would be ideal, she thought to herself while trying to read the malicious expressions her hosts were wearing.

She was about to give her answer before the lights went out.


Jessie heard a familiar voice saying, “C’mon, follow me!” before a small paw took hold of her hand and pulled her into a running sprint. She was shocked, but could not be happier to see her friend, especially after what just happened.

“Meowth!” James exclaimed, “I knew you would come!”

“How did you know we were here?” Jessie asked breathlessly as they ran down the dark hallway.

“Jimmy here left me a message at the shop to meet you guys here,” the cat told them. “He said ya might need backup.”

“He couldn’t have been more right,” Jessie mumbled. She was completely blindsided by the whole scam, and a little upset with herself for not seeing it coming.

“We’ve missed you so much, Meowth,” James told their friend. “That shop needs to cut you a break once in a while!”

“Ya not wrong, Jimmy, but we’ll talk later. Where do ya parents keep the dough?”

James led them to a hidden room on the other side of the mansion. After taking a minute to open the encrypted doors, he pushed them open to reveal an unbelievable pile of gold and riches. It looked all too easy, like something out of a pirate adventure, and Jessie couldn’t wrap her head around it.

“Here it is, guys. Everything we’ve ever wanted.”

The three were already laying down on top of the pile and laughing, enjoying the promise of wealth and each other’s company while they still could. Wobbuffet came out of his Pokeball with delight and joined his friends.

“God, imagine how powerful we could be if we had a fraction of this!” Jessie said, running her hands through the various gold coins and jewels. “We could have our own Team Rocket! Heck, we could have ten Team Rockets!”

“I don’t know, Jess,” James said, twirling a long, fancy necklace around his finger. “Team Rocket’s got influence, but I rather have the luxury of disappearing.”

Jessie knew she agreed with him. Seeing all this wealth had rightfully given her delusions of grandeur, but what she really wanted more than power over a criminal organization was to be left to her own devices so she could thrive. She thought back to her and James’ conversation about what they would do if they had money, and she pictured the three of them being able to relax by the beach whenever they wanted. She wanted fame and notoriety, but she wanted to earn it with her natural gifts rather than with intimidation and stealing Pokemon. Jessie turned her head to look at James and smiled at him, and he smiled back. She couldn’t help but think he was having a similar fantasy.

“We better get going,” James said, reluctantly getting up. “I’m sure they’re looking for us.”

“Both of youse stuff as much gold as you can in ya pockets,” Meowth instructed. “We aren’t leaving until we can purchase at least two of the Orange Islands.”

The three grabbed as much as they could hold before making their way towards the exit. Jessie and Meowth made it out the door before hearing a yelp behind them.

They swung around to see Jessebelle standing behind James, her hand dug into his shirt keeping him where he stood. She smiled at them wickedly.

“Let go of me, Jessebelle,” James mumbled, and she loosened her grip on his shirt.

“Why, Jamesy, where do you think you’re going with all that money?”

James took a deep breath.

“I wasn’t going anywhere, dear,” he said, biting out the last word. “My friends were just leaving.”

Jessie and Meowth stood there, stunned by James’ change of heart.

“James, are you sure-“

“Jimmy, ya can’t stay with her! She’ll eat ya alive-“

“Please, guys,” he cut them off, sighing. “All of this has been planned out and is what has to happen. It’s my destiny. I hope you find yours.”

Jessebelle’s grin grew impossibly wide as she waved off the two.

“Lovely seein’ you both,” she said to them in that terribly sweet voice of hers, still keeping her grip on James’ shirt.

Jessie looked at James’ face. His eyes had started to well up, but he held eye contact with Jessie to assure her that this was okay, and he knew what he was doing. She nodded, trusting her partner to be able to take care of himself, before grabbing Meowth and taking off down the corridor.


Jessie sighed as she looked out at the water. She was sunbathing by the beach, now no longer burdened by several of her biggest problems. It still didn’t feel right, however.

Jessie and Meowth had made it back to Alola, riches on hand. Knowing their track record with money and consistent bad luck, they quickly began the process of purchasing one of the many beach houses she adored. Jessie had left Giovanni a colorful voicemail explaining just what she thought of him, and was now ignoring her buzzing phone. She no longer needed Team Rocket to survive now that she had the means to take care of herself and her friends, which did make her smile. One of her friends was missing from their presence, however, and the thought made her less excited about things to come.

“Ya think Jessebelle has ‘im chained up somewhere?” Meowth said at her side, laying on his own towel on the sand. “Is that why we haven’t heard from ‘im?”

“No, I’m sure she’s just ‘discouraged’ James from contacting us,” she sneered. “Besides, we did basically accept her offer by taking the money and running.”

Meowth sighed. “Poor Jimmy. He’d love ta’ be tanning right now.”

The two said nothing more on the topic as they lay relaxing, occasionally talking about their plans for the near future. It was late afternoon, and Meowth was close to falling asleep.

“Imma take a cat nap, Jess,” he told his friend, rolling up his towel, “I’ll see ya at the bar for Trivia Night?”

Jessie rolled her eyes at how silly it sounded, but nodded in agreement.

“I’ll be here.”

Before she knew it, an hour had passed. The air got slightly chillier, and she watched as the sun drew closer and closer to the horizon. She sighed as she wished Meowth was still here so she could enjoy it with him. This was probably the hundredth time she had seen the same sunset, and stunning as it was, it was something she wanted to experience with someone else. She had sent James pictures of it many times, but it wasn’t the same.

“Not that your photography skills are slacking, but this sunset is even more beautiful in person.”

Shocked by the sound of his voice, she couldn’t believe her eyes when she turned around. He was standing in the sand wearing an Alolan shirt and shorts, his hair pulled back and a large grin on his face.

“James…?” She said, in disbelief. “W-what are you doing here?”

“You should know by now that I wouldn’t stay with those monsters for any period of time unless I was planning to get money out of it,” he told her with a smirk, arms outstretched. She laughed and collapsed into his arms.

“Hey, me and Meowth got the money, who says we’ll share?”

She pulled back from him so she could see his reaction to her teasing, laughing at the exaggerated pout on his face.

“There’s no room for me in the beach house?”

“The one we’re looking at only has four bedrooms, you know. I require at least three.”

“Right, I’ll just crawl back to hell then,” he said, attempting to walk away from her. She laughed before pulling him back by the hand.

“I missed you, you know,” Jessie told him, trying to avoid his eyes. “Texting is fine, but it’s nothing compared to having you… here.”

“Yeah, ’cause you look ridiculous trying to do our motto by yourself.”

“Like you could it better?”

James laughed. “You’re right. I can rock your skirt, but the hair is a challenge I am not prepared for..”

Jessie laughed, making James laugh more. When they both stopped laughing, they caught each other’s’ eyes and shared a brief look of apprehension. James took a deep breath before taking a small step back, his hands still held by Jessie’s.

“Jess, I guess all of this… has made me realize that I have… stronger feelings for you than I thought, and…”

Jessie smiled softly upon hearing this, raising a hand to stroke his face with her thumb. James paused his speech and sighed happily, allowing her to get closer and kiss him. At the touch of his lips, Jessie felt not just bliss, but also wonder as to how they’d never done this before. She pulled back so that she could press her forehead against his and catch her breath.

“Alright, you can have half of one of my bedrooms.”

“What will another kiss get me?”

“Maybe a bathroom. There’s only three and a half.”

James laughed, looking to his right at all the beach houses along the shore.

“Which one will be ours, Madam?”

“Not so fast, James. You have to blend in with the locals here first.”

James scoffed and gestured to his outfit.

“Not good enough. They make you attend at least one Trivia Night.”

“Well, show me the way,” he told her, offering his hand.

“It also happens to be at my favorite bar. I’ve become a bit of a regular around here…”