Chuck was really awesome in particularly niche roles for a few years between 2007-2012. He worked great in Chikara, IWA-MS, and PWG; companies that weren't intended to be mainstream, or even taken too seriously. As much as folks can hate on the hand grenade and slow motion spots? They were highly entertaining with the right companies. There's a clip from a PWG show (one of the DDT4 tournaments, IIRC) where it's Best Friends vs. World's Cutest Tag Team (Joey Ryan/Candace LeRae), and Chuck can't bring himself to strike back at Candace, so he walks back to the locker room...only to come back out wearing a dress and a wig before proceeding to go HOUSE EN FUEGO~ (TM Dames) on her. That kind of cheesy buffoonery worked for smaller audiences that wanted high spots and chicanery, and I was, overall, in that camp for a bit.
When AEW started, though, Chuck was about 8 years removed from being a worthy investment, scooped up because he had some indy clout at a time when AEW was basically "a super-indy with prime time TV." Dude was washed, really. He proved he could work serious with runs in EVOLVE and DG:USA, but there's a very real reason he never got looked at beyond occasional job duty (if even) in ROH, TNA, or WWE.
I'm not sure how much of Chuck's awful AEW run was his own doing, being older and lazier and realizing he'd never be more than a curtain jerking JTTS, and how much was Tony K's overt lack of booking skills. Maybe an 80/20 split, because Best Friends were all over the shows for a while, but Chuck always gave off the feeling that he was just there to cash a check and hang out with some of his old locker room pals.
Regardless, it sucks that this is the way his career ends. I hope he has enough saved up to cover his living expenses while looking for some Regular Joe type work, especially with the cost of cereal these days.