Yeah, I'm a Pokemon Fan. I've had a few ideas percolating for an epic saga in my head, but given I've got so many other projects, it never fully materialized. Here Ash has Sebastian Connor has his mentor and teacher. He's the Johto League Champion and is the successor to become the Ecruteak City Gym Leader. He also trains May and Dawn, and all three of them become champions. During the Sinnoh arc, Sebastian approaches Ursula after the Daybreak Contest with an offer to train her, as detailed in this piece.
Hall of Records File 4
Ursula sat on a bench outside the Daybreak Contest Hall. Her delicate fingers dug into the ruffles of her red skirt. Once again she had to endure the embarassment of losing to that annoying girl with the Piplup. There was a small part of her who had to admit the Flame Ice combo used by Mamoswine and Cyndaquil was quite stunning, but it didn't hide the fact she still lost to that no talent hack! It should have been a guaranteed win with Plusle and Minun, given Dawn's past with the Cheering Pokemon, but the blue haired bitch had managed to squeak by with another victory and she was going to the Grand Festival!
"It's frustrating, isn't it?" a deep voice said from behind her. Ursula turned to see Sebastian leaning up against the wall. "Knowing you had a surefire strategy, you can sense victory is inches away from your grasp. And then it all blows up in your face." He took a breath, taking seat next to her, "I really hate it when that happens. But of course, who likes to lose? I know I don't."
"Your point being?" Ursula hissed, trying to wipe the tears from her face. "Did you come to rub it in?" To her surprise Sebastian just gave a gentle smile, pushing a strawberry ice cream cone into her hand. "What's this for?"
"You just look like you need it." Sebastian said, Ursula took the ice cream and began licking at it. "I'm here with a little proposition. When I saw you battle Dawn both times…and lose. I saw into your eyes." Sebastian pointed at her, "I saw your anger, your frustration, and I also saw a question. 'What is it that Dawn has that I don't?' The answer to that is sitting right in front of you." He indicated to himself. "What Dawn has…is me as her coach. Where do you she learned it all? I helped her perfect all her moves, helped her train her Pokemon to be the best they could."
"That's not to say you're bad, just the opposite in fact, Ursula. You are a genuinely talented Coordinator. Easily Dawn's equal. I remember watching your appeal during the Chocovine Town Contest with your Wormadam. I could tell immediately how hard you worked to refine it, because it was so beautiful. And the double battle you just had with Dawn was nothing short of art in motion! I made it a point to keep an eye on you after the Chocovine Contest, because if there's one thing I pride myself is a being a good judge of talent."
Ursula blushed, "It's nice to finally hear someone acknowledging my skill and hard work. So what are you getting at here? What is it you want?"
"I would like to coach you, Ursula Ashford, because I see a potential Grand Festival Champion in the making, I really do. All you have to do is say yes…it's that simple, my dear." Sebastian took Ursula's hand, kissing it lightly. The peach haired girl blushed some more as Sebastian stood up. "I'll give you some time to think about it. Since I'm sure you're going to be at the Grand Festival. You can let me know then. Until then you have a safe trip, Miss Ashford." He walked off, leaving her alone. Ursula held a hand to her face, the warmth burning in her cheeks.
Ultimately, Ursula would have agreed after losing to Dawn in the Grand Festival. Traveling with the gang the rest of the way through Sinnoh and attending the Lily of the Valley Conference where Sebastian and Cynthia have an epic full battle. Ash takes on Paul and later becomes Sinnoh League Champion.