Well Gen 1 E4 does have a champion (Lance from gen II) AND a hacked Dragonite (Lance from gen II) as well as two pseudo legends (Lance from Gen II Manga). Not to mention, they wrecked all of Kanto with a flick of Agatha's finger (Manga).
I'd say they win.
Gamefreak better add a feature that can topple this fairy type.
Drake just stands dramatically in the light with his jacket billowing behind him, and the sheer force of his Drake-ocity and incredible moustache leads all the other E4s to bow before him.
But then Drayden shows up and it's Drake vs Drayden for best Dragon user ever, settled by who can wrestle the most dragons in 30 minutes. Lance just sits in the corner weeping for his masculinity and Iris is there rooting on Drayden. It ends when in a tie as Drake and Drayden suplex Reshiram and Zekrom into each other.
'Success rates are but scientific theory. A brave heart will defy any odds!' 'Don't beg for things, do it yourself or else you won't get anything.'