I'm... not sure what you're picturing here. Is the idea he'll leap into the air and grab it as Gildedguy is tossing it? What stops him from playing area denial with his Long Sword or just flat out hitting him in an intercept? Mobility isn't the same thing as raw speed, and just being in the air isn't going to stop someone with kilometers of range to work with.
I hold to my statement about mobility, and in turn mobility is something Gildedguy can get around by just restraining them with the pen. Even without him being the best at doing it,
it's still something that can tie the hands of guys on par with him, use that to tie Cinner's legs and that causes way more of an issue.
It goes both ways given Gildedguy's showings in this ballpark, but the fact he has a sword rather than a staff means he can really sever a limb or two to invoke this issue, at least given enough time to work with. Really it's generally going to be a very drawn out battle, so when I say things don't get the impression it'd happen immediately or even super soon, just eventually.
It's not a matter of him being hit, it's lifting strength. He could get his hand (Or his pen, really that makes getting anywhere near GildedGuy at all with a melee implement a risk) on that object and exert 100x the force Cinner can to get it out of his hands or away. And melee is very well where that advantage will be most prevalent, because without range that's going to be easier and easier to pull off.
I don't know where you're getting this from. I guess he did lose when it was destroyed vs Jade, but that seemed more like a tournament rule rather than him surrendering or being significantly weakened, and we see him very much so operate at peak condition with not only a stab wound through his arm but
half of his armor still on his body. Heck he beat Bog specifically when the thing leaked through his armor and into his blood.
The terrain isn't really durable enough to take 8-A hits reliably and we know Gildedguy
can just lash out by spinning around in his longsword if he loses line of sight, so that's not really risk free.
I mean, how complete is this forcefield's insulation anyways? It says it's a sphere that lasts for a time or a certain amount of attacks, can he just poke through it anyways? If so, that still means his weapon is poking out and could be grabbed.
That wasn't a skill issue,
Andre pretty clearly is just overpowering them both at once on top of being generally good at a fight. You don't borderline no sell a rush of attacks on either side of you (which did hit, you can see he's not really blocking all of them) and repel their assaults by just skillgapping someone.