I would need to rewatch a lot of it as I haven't watched it pretty much since it was happening but Kingston is probably the MVP for the entirety of Chikara.
Even in the early years when it's a bunch of half trained guys having bad matches, Kingston manages to stand out even if it's through just engaging the crowd of 20 people. I'm making my way through Chikara at the moment so I'll try and post a list eventually of his best Chikara matches but by and large it will help strengthen his case. The best matches at least until where I'm up to in 2005 are his singles vs Chris Hero (August 27th 2004) and the match where he tags with Mickie Knuckles to take on Quack & Hero (Feb 19th 2005) (though that's more about Hero vs Mickie than anything else but Kingston is great in it too).
He'll be my high on my list, not exactly sure where and I think his AEW run will determine his final standing but he's an easy top 50 for me at the minute.
