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Despite what the tabloids may have gotten convinced of—be it that he was barely into his twenties, well into his forties or plain immortal—Grimsley is, in fact, the oldest of the four Unovan Elites.
He is not, however, the person to hold the title the longest. In fact, after Caitlin, he's held it the shortest despite the fact that it's been years by now.
Surprisingly enough, it's Shauntal who's had the position the longest out of the current four. From what he's heard, Shauntal had been dead-set on the position after attaining an ungodly amount of inspiration due to her own league challenge back in the day.
After that, Marshal acquired his position, a surprise to absolutely no one who followed the league information, really. Marshal is the by now former champion Alder's mentee and had a true passion for battling. Being able to balance that with his work as a martial artist meant he was more suited in the Elite than making a try for the Champion's seat. In other words, this position is working out pretty much perfectly for him.
Grimsley himself had simply been looking for more and more thrill at the time. A sort of thrill that any sort of gambling couldn't give him. He would actually argue that there was some gambling to do before a match but either way, he's quite content now with the way things are.
Then as the last of their current quartet is Caitlin, who came all the way from Sinnoh. She was never one to talk much of things gone by but she did mention she felt more content where she was now.
And that was really all to be said about it.
At first glance they were as different as four people could truly be. But after a while, it seemed almost too apparent they all clicked together unnaturally well. It was an odd kind of chemistry that the previous holders of the Elite's titles had never truly managed—they had mostly been co-workes and friends to some degree. At least, that's what Shauntal as well as the tabloids had said—only accentuated by the fact that they were all roughly the same age.
Not that many were truly aware of that fact. Then again, Grimsley was more than aware of the fact that literally everyone was more obsessed with them as people rather than their age.
After all, Grimsley is allegedly a cryptid, living in a limbo between some way too young age and immortality. Then there is Caitlin, an actual psychic that uses it to make her hair float around to appear like a goddess to intimidate challengers. There is Shauntal and her disgusting collection of horror books that Grimsley has seen the drafts of after having been shown them by the proud little freak (and truly he couldn't love it more despite the fact that he wanted to). Marshal is by hearsay the most normal person of the Elite Four, but then again, there has to be a reason for him to stick around a bunch of weirdos, right?
In either case, every member had always enjoyed, in one way or another, to leave the tabloids guessing at the truth. Be it personal amusement or a wish for some sense of privacy at having spread half a lie.
This little game of theirs started almost immediately as they took their positions and it kept going even now.
The only thing that did change (and mostly just grew) was their affection for one another.
If you asked anyone who started this game of seduction they would tell you it was Grimsley, if only for the fact that he's a natural flirt due to his dramatics.
(Then again, you don't become good at the kind of things Grimsley is good at by being a plain person.)
Despite the fact that Grimsley would flirt with anyone his age no matter what—if only for the thrill of it—none of them had truly planned things to go the way they did.
After all, no one had really anticipated the fact that Shauntal accidentally flirted just as hard as Grimsley did with her natural charm and easy way of earnestly complimenting those around her with flowery words.
Secondly, no one had assumed that Marshal would ever be so delightfully flushed at the mess of it all while both his gentleness and his confidence made him all the more alluring.
Everyone had then also greatly underestimated Caitlin's charm as she showed more and more affection as the time passed around them.
And then as a nail to the coffin (a saying Shauntal loved a bit too much, actually), Grimsley realised too late he'd lost interest in anyone but them while his flirtatious words became more genuine than just to seek that thrill of affection.
And frankly, they were all the fools, because it worked out a little too well to have even the slightest bit of reservation about it.
And as such, their relationship status was probably the thing the four of them loved to see the tabloids guess at the most.
Their little makeshift family later—rather, not actually that long ago—became somewhat literally that as Iris took over the Champion's title from Alder.
It was all fine and well, especially because Iris seemed to take her task more seriously than Alder ever had. And yes the situation with Alder might have only gotten the way it did after the passing of his beloved partner, but that didn't stop all the work from falling on their shoulders when the, at that moment, champion disappeared to any part of the region for Dragons knew how long.
Then again, dutiful as Iris may be, she is still a child, and that meant they still would be taking care of most of the league duties. At least the kid was dead-set on helping in some way. Shauntal was adored by it. Caitlin mostly seemed to be glad she would have less of someone else's work on her plate.
Marshal took everything as it was, probably also being the most understanding in Alder's situation seeing as the martial artist is, as ever, the closest to the former champion.
Grimsley himself didn't mind some extra work, per se, as long as he could drown out the extra stress in whatever way Marshal definitely didn't approve of.
Frankly it's not as if the kid really needed them to babysit and/or guide her, the girl is a genius in her field and can speak to the heart of any dragon. The matter is simply this:
No one wants the wrath of the Opelucid mayor on them.
Old as he may be, even Marshal wouldn't even consider doing anything to get on his bad side (that is, if Marshal could be convinced to do something underhanded in the first place). Who could blame him, anyway, when the old mayor literally wrestles with his Pokémon.
And so, without any sort of complaint they unofficially adopted the region's champion, leaving the tabloids to scream once more.
And truly, it was, as always, a delight to the four of them.